Category: pyrimidines

Electric Literature of C5H11NO. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: (S)-3-Methoxypyrrolidine, is researched, Molecular C5H11NO, CAS is 120099-61-8, about Novel 7-formyl-naphthyridyl-ureas derivatives as potential selective FGFR4 inhibitors: Design, synthesis, and biological activity studies. Author is Sun, Chang’an; Fang, Lei; Zhang, Xiaobing; Gao, Peng; Gou, Shaohua.

Total twenty-five 7-formyl-naphthyridyl-urea derivatives were designed, synthesized and evaluated for their inhibition of FGFR4 kinase and antitumor activity. The pharmacol. data indicated that most of the tested compounds showed high selectivity towards FGFR4 kinase and could significantly inhibit FGFR4 and the tumor cells lines with the high expression of FGFR4. In particular, compounds 6f, 6g, 6h, 6l, 6m and 6s showed a good performance in pharmacokinetic tests. When tested in mice, the representative compound 6f was found to have good pharmacokinetic parameters, low toxicity, and better tumor inhibiting activity in vivo.

In some applications, this compound(120099-61-8)Electric Literature of C5H11NO is unique.If you want to know more details about this compound, you can contact with the author or consult more relevant literature.

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Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Aminoalkylphenols as antimalarials. II. (Heterocyclic amino)-α-amino-ο-cresols. The synthesis of camoquin》. Authors are Burckhalter, J. H.; Tendick, F. H.; Jones, Eldon M.; Jones, Patricia A.; Holcomb, W. F.; Rawlins, A. L..The article about the compound:4-Chloro-8-methylquinolinecas:18436-73-2,SMILESS:CC1=C2N=CC=C(Cl)C2=CC=C1).Recommanded Product: 4-Chloro-8-methylquinoline. Through the article, more information about this compound (cas:18436-73-2) is conveyed.

In view of the high antimalarial activity of certain substituted α-amino-ο-cresols, earlier work (C.A. 41, 414d) has been extended to analogs containing heterocyclic nuclei. This reports the preparation of a group of 122 (heterocyclic amino)-α-amino-ο-cresols and a related group of 12 (heterocyclic amino)benzylamines, as well as the new intermediates used therein. This work has resulted in the preparation of a promising antimalarial (SN 10,751) named camoquin, as well as other compounds which are the most active 4-aminoquinoline derivatives heretofore reported in trophozoite-induced Plasmodium gallinaceum infection in the chick. Catalytic reduction of the appropriate nitrophenol in the presence of Ac2O gave these 4-acetamidophenols: 2-Cl, m. 144°, 55% yield; 2-Ph, m. 160°, 60%; and 2-acetamidophenols: 4-Cl, m. 186°, 52%; 4-Ph, m. 165°, 89%; and 4-tert-Bu, m. 170°, 79%. 2-Allyl-4-acetamidophenol, m. 93-4°, was obtained in 83% yield from the rearrangement of 4-CH2:CHCH2OC6H4NHAc. The Mannich reaction on the substituted acetamidophenols gave these 4-acetamido-α-substituted-ο-cresols: diethylamino (I), m. 135°, 82%; dibutylamino, m. 73°, 87% (picrate, m. 183-5°); dibenzylamino, m. 230°, 75%; (2-methyl-1-piperidyl) (HCl.H2O, m. 175°, 65%); 4-morpholinyl, m. 133°, 27%; [methyl(2-hydroxyethyl)amino] (HCl, m. 198°, 50%); (2-butylamino), m. 156°, 37%; (2-hydroxyethylamino) (HCl, m. 230°, 31%); the 6-allyl derivative of I, m. 86°, 58%: the 5-acetamido isomer of I (HCl, m. 210°, 33%); and these 6-acetamido-α-diethylamino-4-substituted-ο-cresols: Cl (HCl, m. 212°, 66%); tert-Bu (HCl, m. 158°, 53%); and Ph (HCl, m. 183°). Acid hydrolysis of the appropriate 4-acetamido compound gave these 4-amino-α-substituted-ο-cresols (di-HCl salts) (all m. with decomposition); diethylamino, SN 12,458, m. 218-20°, 96%; 1-piperidyl, m. 153-5°, 91%; and 4-morpholinyl, m. 259-60°, 45%. The Mannich reaction on 4-nitrophenol (A) and the reaction of the amine on 2-(chloromethyl)-4-nitrophenol (B) were used to prepare these α-substituted-4-nitro-ο-cresol HCl salts (all m. with decomposition): diethylamino, A, m. 224°, 40%; diisopropylamino, B, m. 193°, 19%; dibutylamino, B, m. 176°, 75%; diisobutylamino (free base), B, m. 113°, 43%; diisoamylamino, B, m. 132°, 32%; isopropylamino, B, m. 238°, 38%; isobutylamino, B, m. 247°, 29%; tertbutylamino, B, m. 275°, 20%; 1-piperidyl, A, m. 260°, 68%; and α-diethylamino-4-nitro-6-phenyl-ο-cresol, A, m. 125°, 21%; and 4-tert-butyl-α-diethylamino-6-nitro-ο-cresol, A, m. 103°, 50%. The method of Price and Roberts (C.A. 40, 5739.5) was used to prepare these substituted 4-chloroquinolines: 6-Me, m. 55°, 50%; 6-anilino, m. 148°, 6%; 7-EtO, m. 76°, 53%; 7-hexyloxy, a high-boiling liquid, 41%; 8-Me, m. 99°, 71%; 5,7-di-Me, m. 59°, 51%; 5,8-di-Me, m. 51°, 59%; 5-chloro-8-methoxy, m. 127°, 6%; 5-methyl-8-methoxy, m. 78°, 45%; 6,8-di-Me, m. 90°, 82%; and 6,7,8-trichloro, m. 156°, 39%. The (heterocyclic amino)-α-alkylamino-ο-cresols were prepared by minor variations of the general procedure of heating the chloroheterocycle with the amino-α-alkylamino-ο-cresols in aqueous or alc. solution on the steam bath. The latter were obtained either by acid hydrolysis of the acetamido derivatives or by catalytic reduction of the nitro derivatives and were usually condensed without isolation. The products are isolated either as the free bases or HCl salts. All the quinine equivalents (Q) reported here are based on the B4 test using P. gallinaceum in the chick. Nearly all the HCl salts m. with decomposition and are colored yellow to orange. 4-(4-Quinolylamino)-α-diethylamino-ο-cresol (II) di-HCl, SN 12,452, m. above 300°, was obtained in 48% yield and had a quinine equivalent of 3 (designated hereafter in the form Q 3). Analogs of II, substituted on the quinoline nucleus: 2-Cl (2HCl, SN 11,986, m. 248°, 30%, Q <0.07); 3-Ph, SN 11,631, m. 155°, 31%, Q 0.4; 6-MeO (2HCl, SN 10,274, m. 270°, 75%, Q 8); 6-Cl (HCl.0.5H2O, SN 11,597, m. 220°, 60%, Q 3.0); 6-Me, SN 11,559, m. 172° (2HCl, m. 238°, 56%, Q 4); 6-anilino (2HCl.H2O, SN 12,361, m. 196°, 63%, Q 0.2); 6-dimethylamino (3HCl.0.5H2O, SN 11,984, m. 235°, 73%, Q 2.5); 6-nitro (2HCl.1.5H2O, m. 210°, 63%, Q 0.8); 7-MeO (2HCl.0.5H2O, SN 11,554, m. 210°, 43%, Q 7); 7-EtO (2HCl.2H2O, SN 11,281, m. 136°, 44%, Q 7); (7-hexyloxy, SN 11,634, m. 153°, 35%, Q 0.5; Q 7); 7-Me (2HCl, SN 12,699, m. 245°, 93%, Q 9); 7-Cl (camoquin) SN 10,751, m. 208°, 86%, Q 25 (2HCl.0.5H2O, m. 243°); 2HCl.H2O, m. 183°; (2HCl.2H2O, m. 160°, 90%); 8-Cl, SN 11,551, m. 212° (2HCl.0.5H2O, m. 253°, 79%, Q 0.5); 8-MeO (2HCl.1.5H2O, SN 11,594, m. 241°, 50%, Q 0.8); 8-Me (2HCl.H2O, SN 11,601, m. 253°, 66%, Q 0.7); 5-chloro-3-Me (2HCl, SN 11,985, m. 258°, 48%, Q 0.3); 5,7-di-Cl (2HCl, SN 12,700, m. 200°, 65%, Q 3); 5,7-di-Me (2HCl, SN 11,561, m. 242°, 67%, Q 10); 5,8-di-Cl (2HCl.H2O, SN 11,596, m. 235°, 60%, Q 0.25); 5,8-di-Me (2HCl, SN 11,560, m. 249°, 80%, Q 0.6); 5-chloro-8-methoxy [2HCl, SN 12,162,(incorrectly given as 12,161 in original), m. 231°, 80%, Q 0.4]; 6-methoxy-2-Me (2HCl, SN 9223, m. 278°, 45%, Q 1.2); 6-methoxy-2-Ph (2HCl.1.75H2O, SN 11,592, m. 198°, 61%, Q 0.25); 6,7-di-Cl (2HCl, SN 12,161, m. 257°, 71.5%, Q 5); 6,7-di-MeO (2HCl, SN 13,395, m. 258°, 68%, Q 2.5); 6,7-di-Me, SN 11,990, m. 215°, 49%, Q 6; 6,8-di-Me (2HCl.H2O, SN 11,558, m. 264°, 54%, Q 0.6); 7-chloro-2-Ph (2HCl, SN 11,232, m. 260°, 41%, Q 0.3); 7-chloro-3-Ph, SN 12,228, m. 165°, Q 1; 7-chloro-3-Me (2HCl, SN 10,492, m. 260°, 64%, Q 6); 8-methoxy-5-Me (2HCl, SN 11,632, m. 210°, 90%, Q 0.6); 6,7,8-tri-Cl (2HCl, SN 11,633, m. 277°, 40%, Q <0.3); and 6-HO (2HCl, SN 11,563, m. 262°, 64%, Q 0.2) (prepared by HBr demethylation of the 6-MeO derivative). 4-(6-Methoxy-4-quinolylamino)-α-dibutylamino-ο-cresol (III) (2HCl.1.25H2O, m. 193°, 10%, Q 9); the (7-chloro-3-methyl-4-quinolylamino) analog of III (2HCl.1.5H2O, m. 177°, 43%, Q 10). 4-(6-Methoxy-4-quinolylamino)-α-1-piperidyl-ο-cresol (IV) (2HCl.0.5H2O, SN 12,038, m. 270°, 80%, Q 8); analogs of IV: (6,7-dimethoxy-4-quinolylamino) (2HCl, SN 13,413, m. 230°, 40%, Q 4); (7-chloro-3-methyl-4-quinolylamino) (2HCl, SN 12,360, m. 270°, 47%, Q 2); (6-methyl-4-quinolylamino) (2HCl, SN 12,456, m. 240°, 41%, Q 2.5). 4-(6-Methoxy-4-quinolylamino)-α-4-morpholinyl-ο-cresol (V) (2HCl, SN 11,989, m. 265°, 57%, Q 1); analogs of V: (7-chloro-3-methyl-4-quinolylamino) (2HCl, SN 12,362, m. 242°, 33%, Q 0.15); (6-methyl-4-quinolylamino), SN 12,457, m. 239°, 50%, Q 0.8. 5-(7-Chloro-4-quinolylamino)-α-diethylamino-ο-cresol, SN 13,730, m. 173°, Q 9; 6-(7-chloro-4-quinolylamino)-α-diethylamino-4-(diethylaminomethyl)-ο-cresol-1.5H2O, m. 145°, Q 5; 4-chloro-α-diethylamino-6-(6-methoxy-4-quinolylamino)-ο-cresol (2HCl, SN 12,885, m 205°, 50%, Q 0.5). 6-Chloro-4-(7-chloro-4-quinolylamino)-α-diethylamino-ο-cresol (VI), SN 13,729, m. 225°, Q 12; analogs of VI: 6-Ph (0.5H2O, m. 235°, 25%); 6-allyl, SN 11,991, m. 148°, 44%, Q 10; 6-allyl-α-1-piperidyl, SN 12,697, m. 190°, 32%, Q 4; 6-allyl-α-diallylamino, SN 13,394, m. 131°, 25%, Q 0.7. 6-Allyl-α-diethylamino-4-(6-methoxy-4-quinolylamino)-ο-cresol, SN 12,039, m. 161°, 33%, Q 7. Variations of the alkylamino group on the cresol portion of camoquin were studied: α-amino-4-(7-chloro-4-quinolylamino)-ο-cresol (VII) (2HCl.0.5H2O, SN 1603, m. 325°, 80%, Q 6); analogs of VII (substituents on the α-amino group): benzoyl (HCl, SN. 11,557, m. 289°, 80%, Q 0.15); Et (2HCl, m. 280°, Q 40, 4% conversion, prepared by the Mannich reaction of EtNH2, (HCHO)x, and 7-chloro-4-(4-hydroxyanilino)quinoline (HCl, m. above 320°, 94%)); Pr(2HCl.0.5H2O, m. 244°, 24%, Q 30); iso-Pr (2HCl, m. 287° 50%, Q 40); Bu (2HCl, m. 254°, 6%, Q 30); sec-Bu (2HCl.H2O, m. 252°, 3%, Q 50); iso-Bu (2HCl, m. 256°, 65%, Q 75); tert-Bu (2HCl, m. 285°, 36%, Q 40); Am (2HCl, m. 266°, 15%, Q 50); (1-methylbutyl 2HCl, m. 231°, 22%, Q 40); iso-Am (2HCl, m. 279°, 20%, Q 50); hexyl (2HCl, m. 280°, 56%, Q 25); (2-ethylbutyl (2HCl, m. 263°, 15%, Q 50)); heptyl (2HCl, m. 278°, 29%, Q 15); octyl, m. 150°, 15%, Q 2.5; allyl (2HCl, m. 257°, 3%, Q 20); 1-methylallyl (2HCl.1.75H2O, m. 95°); cyclohexyl (2HCl.0.25H2O, m. 252°, 30%, Q 30); 2-hydroxyethyl (2HCl.H2O, m. 182°, 15%, Q 3); 2-methoxyethyl (2HCl, m. 271°, Q 25); benzyl (2HCl, m. 270°, Q 16); (α-methylphenethyl) (2HCl.0.25H2O, m. 243°, 31%, Q 25); di-Me (2HCl, m. 290°, 85%, Q 6); N-ethyl-N-butyl(2HCl, m. 240°, 65%, Q 30); di-Pr, SN 13,835, m. 181°, 11%, Q 25; di-Bu, SN 14,105, m. 164°, 20%, Q 35; diiso-Bu (0.5H2O, m. 166°, 38%); diiso-Am (0.5H2O, m. 135°); dihexyl (2HCl, m. 220°, 40%, Q 0.5); diheptyl (2HCl, m. 203°, 52%, Q 1); dioctyl (2HCl, m. 192°, 46%, Q 0.2); bis(2-ethylhexyl) (2HCl.H2O, m. 154°, 1%, Q 3); methyl(2-hydroxyethyl) (2HCl, SN 12,363, m. 250°, 63%, Q 3); butyl(2-hydroxyethyl), SN 14,824, m. 149°, 22%, Q 12; bis(2-hydroxyethyl), m. 193°, 25%, Q 0.6; dibenzyl (2HCl, m. 235°, 74%, Q 2.5); N-methyl-N-Ph (H2O, m. 140°, 39%, Q 0.07); N-ethyl-N-Ph, m. 131°, 54%, Q <0.05. Further analogs of VII: α-1-piperidyl (2HCl.2.5H2O, SN 11,636, m. 302°, 77.5%, Q 25); α-(2-methyl-1-piperidyl) (2HCl, SN 12,357, m. 288°, 66%, Q 20); α-4-morpholinyl (2HCl, SN 11,987, m. 292°, 60-5%, Q 4). Compounds containing heterocyclic nuclei other than the 4-quinolyl include the following 4-(heterocyclic amino)-α-diethylamino-ο-cresols: 9-acridyl (2HCl, SN 12,356, m. 265°, 45%, Q 1.5); (3-chloro-9-acridyl) (2HCl, SN 12,355, m. 267°, 52%, Q 3); (4-methoxy-9-acridyl) (2HCl, SN 12,164, m. 245°, 50%, Q 0.15); (3-chloro-5-methyl-9-acridyl) (2HCl, SN 11,988, m. 275°, 40%, Q 0.25); 2-quinolyl (2HCl, SN 9559, m. 230°, 48%, Q 0.12); (6-methoxy-2-quinolyl) (2HCl, SN 11,537, m. 237°, 20.5%, Q 0.7); (5-nitro-2-quinolyl) (2HCl, SN 9307, m. 245°, 33%, Q <0.07); (2-amino-4-pyrimidyl) (2HCl, SN 9591, m. 258°, 41%, Q 1.1); [2-(1-piperidyl)-4-pyrimidyl], SN 10,177, m. 156°, 31%, Q 0.4; (2-amino-6-methyl-4-pyrimidyl) (2HCl, m. 245°, 55%); (4-methoxy-2-benzothiazolyl) (2HCl, SN 11,189, m. 163°, 47%, Q <0.07); (6-chloro-2-methoxy-9-acridyl) (VIII), SN 8617, m. 175°, 50% (H2O, m. 117°; 2HCl, m. 280°, 76%, Q 4; 2HCl.2H2O, m. 180°); analogs of VIII: α-(ethylbutylamino) (2HCl, m. 252°, 36%, Q 5); α-dibutylamino (2HCl, SN 11,599, m. 246°, 69%, Q 2.5); α-diallylamino, SN 13,163, m. 158°, 16%, Q 0.5; α-dihexylamino (2HCl, m. 254°, 23%, Q 0.4); α-dioctylamino (2HCl, m. 285°, 20%, Q <0.06); α-1-piperidylamino (2HCl, SN 11,536, m. 287°, Q 0.6); α-hexylamino (2HCl.H2O, m. 226°, 7%, Q 1); α-(2-hydroxyethylamino) (2HCl.H2O, SN 11,233, m. 284°, 90%, Q 0.2); α-benzamido (HCl.0.5H2O, SN 11,589, m. 294°, 95%, Q <0.04). 5-(6-Chloro-2-methoxy-9-acridylamino)-α-diethylamino-ο-cresol (2HCl.0.5H2O, SN 9614, m. 237°, 50%, Q 1); 4-tert-butyl-6-(6-chloro-2-methoxy-9-acridylamino)-α-diethylamino-ο-cresol (IX) (2HCl, SN 11,544, m. 271°, 98%, Q 0.6); 4-Ph analog of IX (2HCl, SN 11,553, m. 274°, 84%, Q 0.5); 4-diethylaminomethyl analog of IX (3HCl.H2O, SN 11,550, m. 257°, 73%, Q 2); 6-allyl-4-(6-chloro-2-methoxy-9-acridylamino)-α-diethylaminο-ο-cresol (X) (2HCl, SN 11,234, m. 233°, 65%, Q 3); α-diallylamino analog of X (2HCl.H2O, SN 13,399, m. 188°, 12%, Q 0.3); and α-1-piperidyl analog of X, SN 12,701, m. 164°, 44%, Q 2. A series of nitrobenzylamines was prepared by condensation of the nitrobenzyl chloride with the amine in absolute EtOH. During the course of this work, 2-(chloromethyl)-4-nitrophenetole,m. 72-5°, was obtained in 75% yield from the chloromethylation of 4-nitrophenetole. The nitrobenzylamines were reduced catalytically in absolute EtOH and the resulting aminobenzylamines without isolation were condensed with the chloroheterocycle. Thus were obtained: N,N-diethyl-3-nitrobenzylamine, b6 145-8°, 60%; 4-nitro isomer (XI) (HCl, m. 162°, 45%); analogs of XI: N,N-di-Pr (HCl, m. 138°, 68%); N-monoisopropyl (HCl, m. 232°, 82%); N-monoisobutyl (HCl, m. 214°, 64%). N,N-Diethyl-5-nitro-2-methoxybenzylamine (XII) (HCl, m. 178°, 72%); analogs of XII: N-monoisobutyl (HCl, m. 176°, 63%); N-monoamyl (HCl salt could not be separated from an impurity of AmNH2.HCl). N,N-Diethyl-5-nitro-2-ethoxybenzylamine (HCl, m. 182°, 56%). 3-(7-Chloro-4-quinolylamino)-N,N-diethylbenzylamine (2HCl.2H2O, SN 11,590, m. 128° (all these HCl salts m. with decomposition), 85%, Q 1); 4-(7-chloro-4-quinolylamino)-N,N-diethylbenzylamine (XIII) (2HCl, SN 12,455, m. 261°, Q 4); N,N-di-Pr analog of XIII (2HCl, m. 255°, 60%, Q 4); the N-monoisopropyl analog of XIII (2HCl salt, m. 303°, 23%, Q 10); N-monoisobutyl analog of XIII (2HCl.H2O, m. 288°, 76%); 5-(7-chloro-4-quinolylamino)-N,N-diethyl-2-methoxybenzylamine (XIV), m. 203°, 64%, Q 25; N-monoisobutyl analog of XIV (2HCl.0.25H2O, m. 194°, 76%, Q 17); N-monoamyl analog of XIV (2HCl, m. 288°, 42%, Q 15); 2-ethoxy analog of XIV (2HCl.2H2O, m. 247°, 73%, Q 8); 3-(6-chloro-2-methoxy-9-acridylamino)-N,N-diethylbenzylamine (XV) (2HCl.0.75H2O, SN 10,984, m. 278°, 55%, Q 0.5); the 4-substituted benzyl isomer of XV (2HCl.0.5H2O, SN 10,028, m. 260°, 92%, Q 0.4); and 5-(6-chloro-2-methoxy-9-acridylamino)-2-methoxy-N,N-diethylbenzylamine (2HCl.0.5H2O, m. 212°, 67%, Q 3). 6-Chloro-9-(4-hydroxyanilino)-2-methoxyacridine, m. 266° (decomposition) (HCl, orange, m. above 300°, prepared in 98% yield from p-NH2C6H4OH and 6,9-dichloro-2-methoxyacridine on the steam bath), failed to undergo the usual Mannich reaction. Failure of this reaction led to the development of the method of synthesis used for all of the heterocyclic derivatives reported in this paper. In some applications, this compound(18436-73-2)Recommanded Product: 4-Chloro-8-methylquinoline is unique.If you want to know more details about this compound, you can contact with the author or consult more relevant literature.

Reference:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: 5-Methylfuran-2(3H)-one( cas:591-12-8 ) is researched.Name: 5-Methylfuran-2(3H)-one.Wei, Yunlong; Zhang, Hong; Wu, Xinxin; Zhu, Chen published the article 《Alkene Difunctionalization Triggered by a Stabilized Allenyl Radical: Concomitant Installation of Two Unsaturated C-C Bonds》 about this compound( cas:591-12-8 ) in Angewandte Chemie, International Edition. Keywords: radical alkynylalkenylation enynylalkenylation alkenes dual function sulfone reagent; alkene difunctionalization; alkyne; allenyl radical; radical reactions; rearrangement. Let’s learn more about this compound (cas:591-12-8).

Radical-mediated difunctionalization of alkenes provides a promising approach to introduce one alkenyl or alkynyl group to target compounds However, simultaneous installation of two unsaturated C-C bonds via alkene difunctionalization remains elusive, attributable to the high instability and transient lifetimes of alkenyl and alkynyl radicals. Herein, we report the photocatalytic 1,2-alkynylalkenylation and 1,2-enynylalkenylation of alkenes for the first time, triggered by the intermol. addition of a stabilized allenyl radical to an alkene. A portfolio of strategically designed, easily accessible dual-function reagents are applied to a radical docking-migration cascade. The protocol has broad substrate scope and efficiently increases the degree of unsaturation

In some applications, this compound(591-12-8)Name: 5-Methylfuran-2(3H)-one is unique.If you want to know more details about this compound, you can contact with the author or consult more relevant literature.

Reference:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called Chemistry of vitamin B6. IX. Derivatives of 5-deoxypyridoxine, published in 1953, which mentions a compound: 148-51-6, mainly applied to , SDS of cas: 148-51-6.

cf. C.A. 47, 8745g. The 5-deoxy derivatives (I) of pyridoxine (II), pyridoxal (III), and pyridoxamine (IV) were prepared and characterized. The I can participate normally in biochemical reactions involving the substituent at the 4-position but cannot be phosphorylated like II, III, and IV. As expected the I had no vitamin B6 activity but were effective antimetabolites. Codecarboxylase has been catalytically hydrogenated to 5-deoxypyridoxine (V); both II and III yielded under the same conditions a mixture of 4-deoxypyridoxine (VI) and V. The absorption spectra of 5-deoxypyridoxal (VII) (recorded) and pure pyridoxal-5-phosphate (codecarboxylase) (VIII) at pH 11.0 and 1.9, resp., are almost identical. The deep yellow color of both VII and VIII in alk. solution together with other absorption characteristics is ascribed to a quinoid structure. 2-Methyl-3-hydroxy-4-methoxymethyl-5-chloromethylpyridine (IX).HCl (2.38 g.) in 125 cc. MeOH was shaken with H in the presence of 2 g. 5% Pd-Darco, the mixture filtered, and the filtrate concentrated to 20 cc. to yield 1.5 g. (75%) 2,5-dimethyl-3-hydroxy-4-methoxymethylpyridine (X).HCl, m. 152-3° (from EtOH-Et2O). IX.HCl (23.7 g.) reduced similarly in 2 equal portions, each one in 600 cc. MeOH with 5 g. Pd catalyst yielded 19.0 g. (94%) X.HCl. X.HCl (1.47 g.) in 50 cc. 4N HCl heated 3 hrs. at 180-90° in a sealed tube, the colorless solution filtered, the filtrate concentrated to dryness, and the H2O removed azeotropically with EtOH and C6H6 yielded 0.96 g. (70%) V.HCl, m. 143-3.5° (from EtOH-Et2O); treated with excess NaHCO3 gave V, m. 181-2° (from EtOH). X.HCl was treated in H2O with NaHCO3, the mixture concentrated in vacuo and extracted with Et2O, the extract evaporated, 3.1 g. of the residual free base heated 18 hrs. with 50 cc. MeOH and 50 cc. liquid NH3 in a sealed tube, the mixture evaporated in vacuo to dryness, MeOH added and removed twice by distillation, and the residue extracted with Et2O to leave 1.86 g. (60%) 5-deoxypyridoxamine (XI); m. 160-1° (from MeOH); 2,5-dimethyl-3-p-toluenesulfonoxy-4-p-toluenesulfonylaminopyridine-HCl, m. 194-5° (from EtOH). A small sample of XI was heated 20 min. with Ac2O on a steam bath, the solution concentrated to dryness, the residue treated with EtOH, distilled to dryness, dissolved in HCl, treated with Darco, neutralized with NaHCO3, chilled, and the crystalline deposit recrystallized from C6H6 containing a few drops EtOH to give 2,5-dimethyl-3-acetoxy-4-acetylaminomethylpyridine, m. 174-5°. V.HCl (5.7 g.) was stirred 2 hrs. at 60-70° with 2.8 g. MnO2, 1.5 cc. H2SO4, and 75 cc. H2O, the mixture filtered, the filtrate concentrated in vacuo, the sirup taken up in 15 cc. H2O, excess solid AcONa added, and the thick, crystalline precipitate cooled, filtered off, and washed with ice water to give 1.30 g. (29%) VII, m. 108-9° (from petr. ether); the aqueous filtrate from VII gave with 2 g. NH2OH.HCl 0.9 g. (18%) oxime of VII, m. 239-40° (decomposition) (from EtOH). To the aqueous filtrate of a similar run were added 12 g. NaOAc and 4.5 g. NH2OH.HCl and the mixture was heated 10 min. on a steam bath to yield 2.43 g. (49%) oxime of VII. VII in CHCl3 treated with excess alc. HCl, the solution evaporated in vacuo to dryness, a little H2O added and removed in vacuo, and the residue treated with CHCl3 yielded VII.HCl, m. 191-3° (decomposition). VII (90 mg.) in 1 cc. H2O was cooled in ice, the pH adjusted to 11 with 6N NaOH, 4 drops 30% H2O2 added, the mixture adjusted to pH 3 with HCl and cooled, and the precipitate washed with H2O, EtOH, and Et2O to yield 70 mg. (85%) 2,5-dimethyl-3,4-dihydroxypyridine, decomposed 262-70°. Crude Ca codecarboxylase (0.5 g.) was suspended in H2O and treated with 0.7 cc. 6N HCl, the mixture filtered, the filtrate diluted to 50 cc. shaken 2.25 hrs. at atm. pressure with H and 0.5 g. 10% Pd-C, filtered and concentrated to dryness in vacuo, the residue dissolved in about 3 cc. H2O, the solution treated with excess solid NaHCO3, filtered, the filter residue washed with H2O, the combined filtrate and washings were concentrated in vacuo to 5 cc., the concentrate extracted 21 hrs. continuously with CHCl3, the extract evaporated, and the residue treated with alc. HCl and precipitated with Et2O to give 0.07 g. V.HCl, m. 140-1°. III.HCl (0.35 g.) was treated with 0.10 g. CaO and 0.17 g. H3PO4 and hydrogenated similarly to give 0.08 g. (24%) VI.HCl, m. 264-5°, and 0.11 g. (33%) V.HCl; the aqueous filtrate left from the CHCl3-extraction was concentrated to dryness, the residue extracted with EtOH, and the extract acidified with alc. HCl to give 0.11 g. (30%) I.HCl. Similar hydrogenation of 0.40 g. I.HCl in 0.3 cc. 6N HCl and 50 cc. H2O for 4-5 hrs. gave 0.16 g. (42%) VI.HCl and 0.09 g. (24%) V.HCl. Attempted similar hydrogenation of V gave only recovered starting material.

In some applications, this compound(148-51-6)SDS of cas: 148-51-6 is unique.If you want to know more details about this compound, you can contact with the author or consult more relevant literature.

Reference:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Heterocyclic compounds can be divided into two categories: alicyclic heterocycles and aromatic heterocycles. Compounds whose heterocycles in the molecular skeleton cannot reflect aromaticity are called alicyclic heterocyclic compounds. Compound: 148-51-6, is researched, Molecular C8H12ClNO2, about Convulsive seizure induced by intracerebral injection of semicarbazide (an anti-vitamin B6) in the mouse, the main research direction is semicarbazide convulsion; antivitamin B6 convulsion.Application of 148-51-6.

Intracerebral injection of semicarbazide-HCl (I) [563-41-7] was more effective than systemic administration in inducing convulsions and tremors in mice. The symptoms were prevented by pyridoxine [65-23-6], aminooxyacetic acid [645-88-5] and acetone [67-64-1], but were enhanced by pyridoxal [66-72-8], pyridoxal phosphate [54-47-7] and other anti-B6 agents. Smaller doses of I were required for induction of the symptoms in vitamin B6-deficient mice than in controls. I applied to the vicinity of the lambda caused running fits, followed by convulsions and tremors.

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Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Degradation of Cyclohexane to Benzene》. Authors are Willstatter, Richard; Hatt, Daniel.The article about the compound:5-(hydroxymethyl)-2,4-dimethylpyridin-3-ol hydrochloridecas:148-51-6,SMILESS:OC1=C(C)C(CO)=CN=C1C.[H]Cl).Product Details of 148-51-6. Through the article, more information about this compound (cas:148-51-6) is conveyed.

cf. C. A., 6, 748.-The prepare of cyclohexene by heating cyclohexanol with (CO2H)2 (Zelinskii and Zelikov, Ber., 34, 3251) gives poor yields owing to the formation (15 g. from 60 g. of alc.) of dicyclohexyl oxalate, (CO2 C6H11)2, quadratic leaves, m. 42°. Brunel’s method (use of KHSO4, Bull. soc. chim. 33, 270) gives an 80% yield, together with (C6H11)2O, b. 97-8.5°,b737 259-40° (Ipatiev and Philipov, C. A., 3, 1014, give the b. p. as 275-7°). Cyclohexene dibromide, heated 9 hrs. at 110-5° in scaled tubes with 6 mols. NHMe2 in 18% C6H6 solution, gave 75% of δ-dimethylaminocyclohexene, b725 89-91.5°, b725 160.5-2.5°. Chloroplatinate, prisms, m. 185°. Methiodide, needles, m. 173-4° 1,3-Cyclohexadiene prepared by Crossley’s method from cyclohexene dibromide and quinoline (J.Chem.Soc., 85, 1403) contains cyclohexene, bromocyclohexene and C6H6 (20% of the latter in 145 g. of the crude product). Obtained pure by Harries’ method (C. A., 6, 108), It b72, 78.3-8.8°, d420 0.8404, nD20 1.47439,nα20 1.47025,nβ20 1.48516, nγ20 1.49491, MD 26.77, Mα 26.59, Mβ 27.19, Mγ 27.55, Mγ-α 0.97. It quickly absorbs 4 ats.H in the presence of Pt. With NHMe2 in cold concentrateC6H6 solution, the dibromide gives quant. Δ2-tetramethyldiaminocyclohexene, b10 90.5-2.5°, b725 219.5-3-5°, d40 0.920. Chloroplatinate, rhombic tablets, blacken 240°, decompose 259-60°. Methiodide, microscopic quadratic tables, m. 236° (decompose); the quaternary base obtained by the action of Ag2O on the methiodide, decompose, on evaporation of the solution, into C6H6 and NMe2, the temperature of decompose depending on the pressure (98-104° at atm. pressure with an 80-5% yield of C6H4; 40-50° under 20° mm.; -3° to 5° under 0.008-0.02 mm.

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Pyrimidine – Wikipedia

Reference of 5-(hydroxymethyl)-2,4-dimethylpyridin-3-ol hydrochloride. So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic. Compound: 5-(hydroxymethyl)-2,4-dimethylpyridin-3-ol hydrochloride, is researched, Molecular C8H12ClNO2, CAS is 148-51-6, about Comparative study of the use of microörganisms in the screening of potential antitumor agents.

Collaborative studies were organized to include 16 microbial systems, with bacteria, fungi, and protozoa as the assay microörganisms. A series of 200 compounds were studied. It appears that 95% of the compounds adjudged to be tumor-active in animal assays can be detected by virtue of their inhibitory effects on microörganisms, with as few as 4 selected bioassay systems. 34 references

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Pyrimidine – Wikipedia

The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: 5-Methylfuran-2(3H)-one( cas:591-12-8 ) is researched.Synthetic Route of C5H6O2.Thatikonda, Thanusha; Deepake, Siddharth K.; Das, Utpal published the article 《α-Angelica Lactone in a New Role: Facile Access to N-Aryl Tetrahydroisoquinolinones and Isoindolinones via Organocatalytic α-CH2 Oxygenation》 about this compound( cas:591-12-8 ) in Organic Letters. Keywords: tetrahydroisoquinolinone preparation; isoindolinone preparation; tetrahydroisoquinoline oxygenation organocatalyst; isoindoline oxygenation organocatalyst. Let’s learn more about this compound (cas:591-12-8).

A method for the direct oxidation of various N-aryl tetrahydroisoquinolines and isoindolines to the corresponding lactams using α-angelica lactone as a catalyst was developed. The utility of the method was further demonstrated by synthesis of indoprofen and indobufen.

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Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic.Gupta, Vijay; Sahu, Debashish; Jain, Shailja; Vanka, Kumar; Singh, Ravi P. researched the compound: 5-Methylfuran-2(3H)-one( cas:591-12-8 ).Computed Properties of C5H6O2.They published the article 《Diastereoselective multi-component tandem condensation: synthesis of 2-amino-4-(2-furanone)-4H-chromene-3-carbonitriles》 about this compound( cas:591-12-8 ) in Organic & Biomolecular Chemistry. Keywords: amino furanone chromene carbonitrile diastereoselective synthesis; multicomponent tandem Knoevenagel Pinner vinylogous Michael condensation sequence. We’ll tell you more about this compound (cas:591-12-8).

A general strategy for a one-pot stereoselective synthesis of 2-amino-4-(2-furanone)-4H-chromene-3-carbonitriles by reaction of salicylaldehyde, malononitrile and butenolides via a tandem Knoevenagel/Pinner/vinylogous Michael condensation is presented. The β,γ-butenolides gave a syn-selective MCR adduct with a dr up to 11.5 : 1. The mechanistic insight into the MCR was obtained by DFT calculations

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Sawaya, Christina; Horton, Roger; Meldrum, Brian published the article 《Transmitter synthesis and convulsant drugs: effects of pyridoxal phosphate antagonists and allylglycine》. Keywords: convulsant brain transmitter pyridoxal phosphate.They researched the compound: 5-(hydroxymethyl)-2,4-dimethylpyridin-3-ol hydrochloride( cas:148-51-6 ).Formula: C8H12ClNO2. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:148-51-6) here.

Glutamic acid decarboxylase (EC 4.1.1.15) (I) [9024-58-2] and dopa decarboxylase (EC 4.1.1.26) (II) [9042-64-2] in mouse brain homogenates were inhibited after administration of methyldithiocarbazinate [5397-03-5] (45 mg/kg, i.p.), thiosemicarbazide [79-19-6] (100 mg/kg, i.p.), or 4-deoxypyridoxine-HCl (III) [148-51-6] (250 mg/kg, i.p.); addition of pyridoxal phosphate [54-47-7] abolished the inhibition. I activity was inhibited by allylglycine (IV) [3182-77-2] in vivo (200 mg/kg, i.p.) and in vitro whereas II activity was unaffected. III (250 mg/kg, i.p.) decreased brain GABA [56-12-2] levels, increased homovanillic acid [306-08-1] and 5-hydroxyindoleacetic acid [54-16-0] levels, and did not alter dopamine [51-61-6] and serotonin [50-67-9] levels. Brain GABA levels were decreased by IV while monoamine and monoamine metabolite levels were unchanged. Inhibition of II activity is not the primary or critical mechanism in the convulsant action of hydrazides and IV.

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Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia