Category: pyrimidines

Zheng, Wen-Na published the artcileSynthesis, crystal structure, herbicide safening, and antifungal activity of N-(4,6-dichloropyrimidine-2-yl)benzamide, Application In Synthesis of 56-05-3, the publication is Crystals (2018), 8(2), 75/1-75/10, database is CAplus.

The compound N-(4,6-dichloropyrimidine-2-yl)benzamide (C₁₁H₇Cl₂N₃O) was synthesized and the corresponding structure was confirmed by ¹H NMR, ¹³C NMR, HRMS, IR, and single-crystal X-ray diffraction. The compound crystallized in a monoclinic system with space group P 2₁/c, where a = 14.9156(6), b = 16.6291(8), c = 14.4740(6) Å, β = 95.160(2)°, V = 3575.5(3) ų, Z = 12, Dc = 1.494 g·cm^-3, F(000) = 1632, μ(MoKa) = 3.182 mm^-1, final R = 0.0870, and wR = 0.2331 with I > 2σ(I). The crystal structure was found to be stabilized by intermol. hydrogen bonding interactions N-H···O and C-H···Cl. Furthermore, the results from biol. assays indicated that the compound showed a similar protective effect on metolachlor injury in rice seedlings compared to fenclorim at a concentration of 4.0 mg·L^-1. Moreover, the compound exhibited an improved antifungal activity compared to pyrimethanil against S. sclerotiorum and F. oxysporum. Potentially, these results lay the foundation for the development of novel herbicide safeners and fungicides.

Crystals published new progress about 56-05-3. 56-05-3 belongs to pyrimidines, auxiliary class Pyrimidine,Chloride,Amine,API, name is 2-Amino-4,6-dichloropyrimidine, and the molecular formula is C12H10F2Si, Application In Synthesis of 56-05-3.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Boon, W. R. published the artcilePteridines. IV. Derivatives of 2,4-diaminopteridine and related compounds, Formula: C6H9N3O2, the publication is Journal of the Chemical Society (1957), 2146-58, database is CAplus.

cf. C.A. 46, 2082g. Several derivatives of 2,4-(H₂N)₂-Y (in this abstract Y = pteridine) possess antimalarial activity (Potter and Henshall, C.A. 51, 1974h). A series of 2,4,6,7-(H₂N)₂Ph₂-Y were prepared in which the H₂N groups were progressively substituted by Me. Antimalarial activity was immediately lost, but the compounds were active against exptl. schistosomiasis in mice. Further modifications of the substituents always lowered the activity. Only a few compounds showed any appreciable activity. 2,4,6-Me₂N-(HO)₂-Z (in this abstract Z = pyrimidine) ground to pass a 30-mesh sieve, added with stirring during 45 min. to 280 cc. AcOH and 65 cc. HNO₃ (d. 1.5) at 20-5°, stirred an addnl. 45 min., the mixture poured into 1350 cc. H₂O, the solid separated, washed free from acid, and dried gave 81 g. 5-O₂N derivative (I). I (5 g.), 60 cc. POCl₃, and 20 cc. PhNMe₂ heated to 105° (bath temperature), after the vigorous reaction the heating continued 1 hr., excess POCl₃ removed in vacuo, the residue treated with 200 g. ice, the suspension extracted with four 50-cc. portions of Et₂O, the combined extracts dried, filtered, evaporated, and the residue crystallized from petr. ether (b. 60-80°) gave 3.7 g. 4,6-Cl₂ compound (II), m. 117-20°. II (14 g.), 90 cc. C₆H₆, and 10 cc. aqueous NH₃ (d. 0.880) shaken overnight, the mixture filtered, and the residue (4.2 g.) crystallized twice from dioxane gave the 4,6-(H₂N)₂ compound, m. 249-50°; evaporation of the filtrate gave a residue which, after chromatography on 120 g. Al₂O₃ in 30 cc. C₆H₆ and crystallization from EtOAc-petr. ether afforded 0.5 g. 4-H₂N compound, m. 132°. To 91 g. Na in 2 l. MeOH was added 509 g. [MeHNC(:NH)NH₂]₂.H₂SO₄, the mixture refluxed 30 min. with stirring, CH₂(CO₂Et)₂ added, the heating continued 6 hrs., the mixture cooled, diluted with 5 l. H₂O, treated with C, filtered, the filtrate acidified to litmus with AcOH, and the precipitate collected to give 183 g. 2,4,6-MeHN(HO)₂-Z (III); the mother liquors deposited 15 g. presumably 2-amino-1,4,5,6-tetrahydro-1-methyl-4,6-dioxo-Z, m. above 360°. III (93g.) and 510 g. POCl₃ refluxed 1 hr., the mixture filtered through sintered glass, the filtrate poured on 2250 cc. 32% aqueous NaOH and ice, the separated solid collected, washed with H₂O, and crystallized from MeOH gave 88 g. 2,4,6-(MeHN)Cl₂-Z (IV), m. 164°. IV (130 g.) heated 12 hrs. with NaOMe (from 168 g. Na in 570 cc. MeOH), the solution cooled, the precipitate collected, washed with H₂O, and crystallized from MeOH yielded 95 g. 4,6,2-Cl(MeO)(MeHN)-Z, m. 153°. Similarly was prepared 81% 4,6,2-Cl(MeO)(Me₂N)-Z (VI), m. 62° (after sublimation at 55°/0.1 mm.), from 4,6,2-Cl₂(Me₂N)-Z at room temperature VI (10 g.) heated 30 min. on a steam bath with 50 cc. HCl, the solution cooled, the product collected, and purified by solution in aqueous alkali, treatment with C, and reprecipitation with AcOH gave 5.5 g. 6-HO compound, m. 265° (decomposition). Similarly was obtained from VI 95% 4,6,2-Cl(HO)(Me₂N)-Z (VII), m. 217°. 4,6,2-ClMe(H₂N)-Z (28.7 g.) and 78 cc. 19.5% alc. Me₂NH heated 17 hrs. at 110-20° gave 172 g. 4-Me₂N derivative, m. 172° (from C₆H₆). Ph(H₂N)CHCOPh.HCl (47 g.) dissolved in 750 cc. H₂O. basified at 0° with aqueous NH₃, the base collected, sucked as dry as possible, added to 35 g. 2,4,6-Cl₃-Z (VIII) in 750 cc. EtOH, the mixture set aside 2 days at room temperature, the precipitate (12 g.) collected, and crystallized from EtOH gave α-(2,4-dichloro-6-pyrimidylamino)deoxybenzoin (IX), m. 165°. p-ClC₆H₄CHBzNH₂ (X) (28.5 g.) converted to the base, the latter treated as above with 9 g. VIII, the crude product refluxed 3 hrs. with 10 cc. 19.5% alc. Me₂NH and 10 cc. EtOH, the solution evaporated to 0.5 its volume, and the solid recrystallized from MeOH gave ω-(4-chloro-2-dimethylamino-6-pyrimidyl-amino)-ω-(p-chlorophenyl)acetophenone, m. 151-2°; the mother liquors gave the 6-Me₂N isomer, m. 181-2° (from EtOH), and a small amount of another compound believed to be 2,5-di(p-chlorophenyl)-3,6-diphenylpyrazine, m. 239-40°. 4,6,2-Cl₂(H₂N)-Z (XI) (33 g.) heated 3 hrs. with 175 cc. 19.5% alc. Me₂NH, after the initial reaction had subsided the solution cooled, the precipitate (24 g.) collected, and crystallized from MeOH and then from C₆H₆ gave 4,2,6-Cl(H₂N)(Me₂N)-Z, m. 164-5°. Similarly were obtained in 70% yield from the appropriate derivative of XI and an alc. solution of H₂NCH₂CO₂Et, Et 4-chloro-2-methylamino-6-pyrimidylaminoacetate (XII), m. 167°, and Et 4-chloro-2-dimethylamino-6-pyrimidylamino-acetate, m. 121°. 2,4,6-Cl₂(Me₂N)-Z (36 g.), 200 cc. EtOH, and 50 cc. 70% aqueous EtNH₂ refluxed 6 hrs., EtOH removed, the mixture diluted with H₂O, extracted with Et₂O, the extract dried, Et₂O removed, the residue dissolved in 70 cc. absolute EtOH, 9 cc. concentrated H₂SO₄ added (the mixture acid to Congo red), and dry Et₂O added to a permanent turbidity gave 34 g. 4,6,2-Cl(EtNH)(MeNH)-Z sulfate, m. 148° (from EtOH-Et₂O). The following compounds were prepared similarly: 4,2,6-Cl(Me₂N)(MeNH)-Z, m. 78° (from petr. ether); 4,2,6-Cl(Et₂N)(MeNH)-Z sulfate, m. 148-9° (from EtOH-Et₂O); 4-chloro-6-methylamino-2-piperidino-Z, m. 118° (from MeOH); 4,6,2-Cl(MeNH)(Me₂NCH₂CH₂NH)-Z, m. 99° (from EtOAc-petr. ether). To 17.5 g. VII in 500 cc. H₂O containing 60 cc. 2N NaOH and 12.6 g. NaHCO₃ was added 4-ClC₆H₄N₂Cl (XIII) [from 12.75 g. 4-ClC₆H₄NH₂ (XIV)], the solution stirred overnight, the precipitate collected, washed with H₂O, EtOH, and Et₂O, and crystallized from dioxane to give 20 g. 5-p-ClC₆H₄N₂ derivative (XV), m. 220-2° (decomposition). 4,6,2,5-Cl(HO)(MeNH)(p-ClC₆H₄N₂)-Z was obtained similarly but could not be purified without decomposition XIII (500 cc. 0.025M) and 46 g. NaOAc.3H₂O (XVI) added with stirring to 3.8 g. 6,4,2-Me(HO)(Me₂N)-Z in 500 cc. H₂O, after 16 hrs. the precipitate collected, washed, dried in air, and recrystallized from BuOH gave 5.5 g. 5-(p-ClC₆H₄N₂) derivative, m. 216-17°. XIII (50 cc. 0.025M) and 40 g. XVI added with stirring to 5.0 g. 4,2,6-Cl(Me₂N)₂-Z in 70 cc. AcOH, diluted with 200 cc. H₂O, after 48 hrs. stirring the solid collected, washed with H₂O, and crystallized twice from EtOH gave 5 g. 5-(p-ClC₆H₄N₂) derivative (XVII), m. 91°. The following N.CX:N.CW:C(N:NR).CY (XVIII) (W = Cl) were prepared (X, Y, R, m.p., crystallization solvent, % yield given): NH₂, NHMe, p-ClC₆H₄, 255°, HCONMe (XIX), 47; NH₂, NMe₂, p-ClC₆H₄, 204°, XIX-EtOH, 65; NHMe, NH₂, p-ClC₆H₄, 272° (decomposition), XIX, 90; NHMe, NHMe, p-ClC₆H₄, 272°, XIX-EtOH, 95; NHEt, NHMe, p-ClC₆H₄, 214°, BuOH, 75; NMe₂, NH₂, p-ClC₆H₄, 229°, BuOH, 90; NMe₂, NHMe, Ph, 163°, EtOH, 78; NMe₂, NHMe, p-ClC₆H₄, 183°, BuOH, 90; HNCH₂CH₂NMe₂, NHMe, p-ClC₆H₄, 158°, EtOH, 50. 6,4,2,5-Cl(H₂N)(Me₂N)(p-ClC₆ H₄N₂)-Z (XX) (2 g.) and 40 cc. saturated alc. NH₃ heated 36 hrs. at 150-60°, the solution cooled, and the product (1.75 g.) crystallized from BuOH gave 6-H₂N compound, m. 272-3° [HCl salt, m. 301° (decomposition) (from 80% HCO₂H) (prepared from XIII and 4,6,2-(H₂N)₂(Me₂N)-Z in AcOH)]. Similarly were prepared the following XVIII (W = NH₂, R = p-ClC₆H₄) (X, Y, m.p., crystallization solvent, % yield given): NH₂, NHMe, 213°, BuOH, 40 and 80; NH₂, NMe₂, 205°, XIX-H₂O, 96; NH₂,

Journal of the Chemical Society published new progress about 5738-14-7. 5738-14-7 belongs to pyrimidines, auxiliary class Pyrimidine,Amine,Alcohol,Pyrimidine, name is 2-(Dimethylamino)pyrimidine-4,6-diol, and the molecular formula is C6H9N3O2, Formula: C6H9N3O2.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Boon, W. R. published the artcile4,6-Dichloro-2-dimethylaminopyrimidine, Quality Control of 5738-14-7, the publication is Journal of the Chemical Society (1952), 1532, database is CAplus.

Me₂NC(:NH)NH₂.0.5H₂SO₄ (91 g.), stirred 30 min. with 300 cc. boiling MeOH containing 15 g. Na, the solution treated with 116 g. CH₂(CO₂Et)₂, refluxed 6 hrs., diluted with 450 cc. H₂O, and acidified with AcOH, gives 85 g. 2-dimethylamino-4,6-dihydroxypyrimidine (I), with 3 mols. H₂O, does not m. at 350°. I (15.5 g.) and 60 cc.POCl₃, refluxed 35 min. and poured into 1 l. cold 2 N NaOH, give 16 g. 4,6-dichloro-2-dimethylaminopyrimidine (II), m. 54°; II also results from the reaction of 2,4,6-tri-chloropyrimidine and Me₂NH on crystallization from petr. ether and aqueous MeOH (cf. King and King, C.A. 42, 1280h). I (3.8 g.) and 10 cc. 10% EtOH-NH₃, heated 18 hrs. at 110-20°, give 4-amino-6-chloro-2-dimethylaminopyrimidine, m. 151°; this results also from 4-amino-2,6-dichloropyrimidine and Me₂NH (10 hrs. at 80°). I and EtOH-MeNH₂ or 2,4-dichloro-6-methylaminopyrimidine and alc. Me₂NH give 4-chloro-2-dimethylamino-6-aminopyrimidine, b₁ 122-5°. Il and EtOH-Me₂NH give 4-chloro-2,6-bis(dimethylamino)-pyrimidine, m. 52.2°, sublimes 56°/0.1 mm.

Journal of the Chemical Society published new progress about 5738-14-7. 5738-14-7 belongs to pyrimidines, auxiliary class Pyrimidine,Amine,Alcohol,Pyrimidine, name is 2-(Dimethylamino)pyrimidine-4,6-diol, and the molecular formula is C6H9N3O2, Quality Control of 5738-14-7.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Jovanovic, Misa V. published the artcileSyntheses of some pyrimidine N-oxides, Synthetic Route of 31401-45-3, the publication is Canadian Journal of Chemistry (1984), 62(6), 1176-80, database is CAplus.

Various monosubstituted pyrimidines and methylpyrimidines were N-oxidized with a number of different peracids. In general, they are more susceptible to side reactions accompanying N-oxidation than other π-deficient diazines and triazines. Unsym. pyrimidines, which can potentially yield 2 isomeric products, were N-oxidized preferentially at the site para to strong electron-donating substituents. Weaker ring-activating groups, such as Me, are mainly ortho-directing and only aid in the N-oxidation of pyrimidine nuclei having ortho/para-directing substituents.

Canadian Journal of Chemistry published new progress about 31401-45-3. 31401-45-3 belongs to pyrimidines, auxiliary class Pyrimidine,Amine, name is N,N-Dimethylpyrimidin-4-amine, and the molecular formula is C6H9N3, Synthetic Route of 31401-45-3.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Kobayashi, Shigeru published the artcileSynthesis of pyrimidines and condensed pyrimidines, COA of Formula: C6H9N3, the publication is Bulletin of the Chemical Society of Japan (1973), 46(9), 2835-9, database is CAplus.

A new one-step synthesis of pyrimidines, e.g. I (R = alkyl) and condensed pyrimidines, e.g., II (n = 2-4) by heating carboxamides or cyclic lactams with formamide in the presence of POCl3 in a sealed tube is described.

Bulletin of the Chemical Society of Japan published new progress about 31401-45-3. 31401-45-3 belongs to pyrimidines, auxiliary class Pyrimidine,Amine, name is N,N-Dimethylpyrimidin-4-amine, and the molecular formula is C6H9N3, COA of Formula: C6H9N3.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Poznanski, Jaroslaw published the artcilePartial molar volume as an important thermodynamic parameter. Application for uracil methyl derivatives, Product Details of C5H6N2O2, the publication is Journal of Molecular Liquids (2005), 121(1), 15-20, database is CAplus.

Quantum mech. calculations of the solvation were performed for all 16 possible methylated uracil derivatives using the Polarizable Continuum Model (PCM) approach. The obtained results were found to reproduce the exptl. data of hydration enthalpies. The decomposition of QM-derived Gibbs energy enabled us to correlate the solute-solvent Gibbs energy interaction with the difference between partial molar volume and mol. volume In aqueous medium, the change of the “effective” solute volume upon dissolution costs 1.8 kJ mol^-1 per every 1 cm³ mol^-1 of the difference between solute partial molar volume and mol. volume

Journal of Molecular Liquids published new progress about 608-34-4. 608-34-4 belongs to pyrimidines, auxiliary class Pyrimidine,Amide, name is 3-Methylpyrimidine-2,4(1H,3H)-dione, and the molecular formula is C5H6N2O2, Product Details of C5H6N2O2.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Robba, Max published the artcileCertain derivatives of diazines. II. Reactions of nitriles of diazines, Related Products of pyrimidines, the publication is Ann. Chim. (Paris) (1960), 414, database is CAplus.

Several thioamides, amidoximes, tetrazoles, imino esters, amidines, and imino ketones containing diazine structures were prepared VII (1 g.) and 14 ml. EtOH saturated at 0° with NH₃ then H₂S, refrigerated 16 hrs., the precipitate removed, dried, and crystallized from EtOH gave 90% 4-thiocarbamoylpyridazine, m. 214-15°. 3-Thiocarbamoylpyridazine, m. 168°, and 2-, 4-, and 5-thiocarbamoylpyrimidine (XVI), m. 225°, 236°, and 170°, resp., were similarly prepared 3-Hydroxy-4-cyanopyridazine (XVII) (1 g.), 10 ml. C₅H₅N, and 0.83 g. Et₃N saturated at 0° with H₂S, the precipitate removed after refrigeration 16 hrs., and a 2nd crop obtained by addition of 15 ml. H₂O gave 89% 3-hydroxy-4-thiocarbamoylpyridazine, m. 305°. XV (0.517 g.) in 0.5 ml. H₂O at 40° treated with 0.34 g. NH₂OH.HCl in 1 ml. H₂O and 1.45 g. Na₂CO₃ in 7 ml. H₂O, the mixture heated 1.5 hrs. at 70-5°, and refrigerated 16 hrs. gave 0.51 g. pyrazine-2-amidoxime, m. 185-6°. Pyridazine-3-amidoxine m. 240°, pyridazine-4-amidoxime m. 209°, 3-hydroxypyridazine-4-amidoxime m. 232°, and 4-pyridine-amidoxime m. 186°. Pyrimidine-2-amidoxime, m. 262°, required 2.3 hrs. heating; 3-hydroxypyridazine-4-amidoxime, m. 305°, was recovered after acidification with HOAc. 5-Thiocarbamoyl pyrimidine (XVI) (0.5 g.), 0.25 g. NH₂OH.HCl, 1 g. Na₂CO₃, 15 ml. EtOH, and 8 ml. H₂O refluxed 8 hrs., the mixture concentrated, and refrigerated 24 hrs. yielded pyrimidine-5-amidoxime, m. 165°. I (0.9 g.), 0.65 g. NaN₃, 1.8 ml. HOAc, and 3 ml. iso-PrOH heated 108 hrs. at 150°, refrigerated 16 hrs., the dried precipitate dissolved in 10 ml. H₂O, and acidified with 10% HCl yielded 1.14 g. 3-(5-tetrazolyl)pyridazine (XVIII), m. 307-8°, after sublimation at 210°/0.01 mm. Similarly prepared were: 4-(5-tetrazolyl)pyridazine, m. 237°; 3-hydroxy-4-(5-tetrazolyl)pyridazine, m. 331°; 2-(5-tetrazolyl)pyrimidine, m. 233°; and 4-(5-tetrazolyl)pyrimidine, m. 266°. XII (1 g.), 0.7 g. NaN₃, 0.57 g. NH₄Cl, and 13 ml. HCONMe₂ stirred 7 hrs. at 125-30°, the solvent evacuated, and the residue worked up as for XVIII yielded 0.872 g. 4-(5-tetrazolyl)pyrimidine, m. 257°. XV (1 g.) in 5 ml. EtOH saturated with HCl at 0°, excess HCl and EtOH evacuated, the residue washed with Et₂O, suspended in 5 ml. EtOH, saturated with NH₃ at -15°, added to 3 ml. saturated NaCl at 0°, extracted with Et₂O, and the extract gave 0.84 g. ethyl pyrazinimidate, m. 49-50°, after sublimation. Similarly obtained were: ethyl pyrimidine-4-carboximidate (XIX), m. 29-30°; methyl pyridazine-4-carboximidate, m. 102-3°; methyl pyridazine-3-carboximidate, m. 79-80°; ethyl pyrimidine-5-carboximidate (XX), m. 87°; and ethyl pyrimidine-2-carboximidate hydrochlorides, m. 64-5°. For XIX, the solution was filtered prior to extraction with Et₂O. XIII (1 g.) treated similarly to XV, the residue washed with Et₂O, and the Et₂O evaporated yielded 0.634 g. XX. The residue on crystallization from EtOH yielded 0.607 g. 5-amidinopyrimidine hydrochloride, m. 213°, also obtained by refluxing 1 hr. 0.545 g. XX, 0.19 g. NH₄Cl, 9 ml. EtOH, and 1 ml. H₂O. For preparation of N-monosubstituted diazinoamidines, 0.0085-0.036 mole nitrile was fused with an equimolar amount of amine at 30-75° (130-150° for XVII), an equimolar amount of AlCl₃ added such that a temperature of 140-220° is reached (170-180° for best yields), the mixture cooled, dissolved in H₂O at 80°, the solution filtered, the filtrate washed with Et₂O, and made alk. with 40% NaOH (Na₂CO₃ for XVII); the amidine was recovered by filtration or extraction with Et₂O or CHCl₃ and purified by crystallization or sublimation. The following 2-(N-monosubstituted-amidino)-pyrazines were prepared: phenyl, m. 104°; o-tolyl, m. 131°, p-chlorophenyl, m. 148°; benzyl, m. 118°; α-naphthyl, m. 128°; β-naphthyl, m. 114°; and p-tolyl, m. 137°. 3-(N-Monosubstituted-amidino)pyridazines: phenyl, m. 121°; p-tolyl, m. 133°; benzyl, m. 92°; p-chlorophenyl, m. 152°; β-naphthyl, m. 137-8°. 4-Analogs: phenyl, m. 160; p-tolyl, m. 167°; p-methoxyphenyl, m. 118°; p-chlorophenyl, m. 149°; β-naphthyl, m. 128°. The following pyridazines: 3-hydroxy-4-(phenylamidino), m. 177°; 3-hydroxy-4-(p-tolylamidino), m. 190°; 3-hydroxy-4-(p-methoxyphenylamidino), m. 178°; 3-hydroxy-4-(p-chlorophenyl)amidino, m. 198°; 3-hydroxy-4-(β-naphthyl)amidino, m. 183°; and 3-hydroxy-4-(2-pyridyl)amidino, m. 197°. 2-(Monosubstituted-amidino)pyrimidines: phenyl, m. 117-18°; o-tolyl, m. 92-3°; p-tolyl, m. 128°; p-chlorophenyl, m. 112°; α-naphthyl, m. 154-5°; β-naphthyl, m. 166°; benzyl, m. 80°. 4-Analogs: phenyl, m. 126°; o-tolyl, m. 104°; p-tolyl, m. 134°; benzyl, m. 72°; α-naphthyl, m. 148°; β-naphthyl, m. 152°; and p-chlorophenyl, m. 135°. VII, PhCH₂NH₂, and AlCl₃ gave, in addition to the amidine, 4-(N-benzylcarbamoyl)pyridazine, m. 80-1°, also prepared from 4-carbomethoxypyridazine. AlCl₃ (0.0095 mole) added in portions to 0.0095 mole each XIII and amine in 25 ml. CS₂, the solution refluxed 3-4 hrs., decomposed in ice-HCl, the product taken up in dilute HCl, and liberated with 20% NaOH at 0-5° gave 10-38% yields of the following pyrimidines: 5-(N-phenylamidino), m. 172°; 5-(p-tolylamidino), m. 190°; 5-(p-methoxyphenylamidino), m. 178-9°; 5-(2-pyridylamidino), m. 151°; and 5-(2-thiazolylamidino), m. 162-3°. MeMgI (0.0283 mole) in 20 ml. Et₂O added to 0.0905 mole I in 30 ml. Et₂O, the mixture stirred 3 hrs., 15 g. ice and 3 g. NH₄Cl added after 16 hrs., the Et₂O layer separated, the aqueous layer extracted with Et₂O, the Et₂O extracts washed with NaCl, dried, and concentrated gave 0.64 g. oil, which chromatographed (Al₂O₃) gave 3-acetylpyridazine (XXI), m. 87-8°, and VI. The aqueous phase stirred 1 hr. with 20% HCl below 5°, neutralized with 40% NaOH, and the product taken up in Et₂O gave addnl. XXI in 27% total yield. 4-Acetylpyrimidine, m. 67°, was obtained similarly. VII (1 g.) in 50 ml. Et₂O and 5 ml. C₆H₆ treated with 0.0283 mole MeMgI and the mixture treated as in the preparation of XXI, yielded 71% 4-(iminoacetyl)pyridazine, m. 78-9°. 5-(Iminoacetyl)pyrimidine, m. 180-1°, was prepared similarly. Et₂NH (0.0042 mole) in 5 ml. Et₂O added to 0.0142 mole EtMgBr in 12 ml. Et₂O, the solution refluxed 20 min., cooled, 1 g. III in 5 ml. Et₂O and 2 ml. C₆H₆ added, the mixture refluxed 2 hrs., and worked up as for XXI then chromatographed gave 0.208 g. 2-(diethylcarbamoyl)pyrimidine, m. 35-6°. XII gave 4-(diethylcarbamoyl)pyrimidine, m. 36-7°, and XI.

Ann. Chim. (Paris) published new progress about 92306-69-9. 92306-69-9 belongs to pyrimidines, auxiliary class Tetrazoles, name is 4-(1H-1,2,3,4-Tetrazol-5-yl)pyrimidine, and the molecular formula is C5H4N6, Related Products of pyrimidines.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Robba, Max published the artcileCertain derivatives of diazines. I. Synthesis of nitriles of diazines, SDS of cas: 92306-69-9, the publication is Ann. Chim. (Paris) (1960), 351-79, database is CAplus.

All six possible nitriles of pyridazine, pyrimidine, and pyrazine were prepared by dehydration of the corresponding amides with POCl₃. 3-Cyanopyridazine (I) was prepared in poor yield from 3-bromopyridazine (II) and 2-cyanopyrimidine (III) from 2-pyrimidinesulfonic acid. α-Oxoglutaric acid (230 g.) in 390 ml. boiling H₂O treated in 20 min. with 160 g. NaOH, 280 g. (N₂H₄)₂.H₂SO₄ and 980 ml. H₂O, heated 5 min., and cooled gave 181 g. 3-hydroxy-6-carboxy-4,5-dihydropyridazine, m. 196°, which by reaction with POBr₃ gave II. 2,5-Dimethoxy-2,5-dihydrofurfuryl acetate (10.1 g.) and 40 ml. N H₂SO₄ boiled 1 min., cooled rapidly, 5 ml. N₂H₄.H₂O added, the mixture refluxed 20 min., the mixture extracted with 7% MeOH-Et₂O, and the extract distilled yielded isopropylideneacetylhydrazine, b₇ 135-40°, m. 133°, and 28% 3-(hydroxymethyl)pyridazine (IV), b₇ 140-165°, m. 66° (Et₂O-petr. ether). IV was oxidized to 3-carboxypyridazine, which was esterified quant. with CH₂N₂ to 3-carbomethoxypyridazine (V), m. 139° (Et₂O). V (27 g.) in 27 g. MeOH and 70 g. saturated NH₃MeOH gave after several days 90% 3-carbamoylpyridazine (VI), m. 182° (H₂O). VI (3 g.) and 15 ml. POCl₃ treated after 1 hr. with 15 ml. PhMe, refluxed 1 hr., the solvent evacuated, the residue desiccated 24 hrs., dissolved in 30 ml. saturated Na₂CO₃ at 5°, the solution extracted with Et₂O, the extract dried, and concentrated gave 70% I, m. 43-4° (Et₂O). Subsequent nitriles were prepared similarly. 4-Cyanopyridazine (VII) could not be obtained by dehalogenation of 3-chloro-4-cyanopyridazine. 4-Carbomethoxypyridazine, m. 63°, yielded 65% VII, m. 79-80°. 2-Methylpyrimidine (3.6 g.), 26 g. NaOAc, and 55 ml. HOAc treated at 90° with 24.5 g. Br in 10 ml. HOAc, the mixture heated 45 min., refrigerated 1 hr., 90 ml. H₂O added slowly, cooling continued 16 hrs., the product removed, and the addition of H₂O and cooling repeated gave 7.3 g. total 2-tribromomethyl-5-bromopyrimidine (VIII), m. 131° (CHCl₃). AgNO₃ (4.7 g.), 11 ml. H₂O, 3.9 g. VIII, and 29 ml. HOAc heated 1 hr. on a steam bath, filtered, the residue washed with boiling H₂O, the filtrate acidified with 4 ml. HCl, extracted with CHCl₃, and the extract evaporated gave 70% 2-carboxy-5-bromopyrimidine (IX).H₂O, m. 191-2°; free IX m. 231°; methyl ester m. 148-9°, 2-carbamoyl-5-bromopyrimidine (0.75 g.), m. 209°, 60 ml. EtOH, 30 ml. Et₂O, 1.2 ml. 20% Na₂CO₃, and 1 g. Raney Ni stirred 3 hrs. at 50° under 3 kg. II pressure, filtered, the solvents evaporated and the residue extracted with hot CHCl₃ yielded 50% 2-carbamoylpyrimidine, m. 166-7°, after sublimation, converted to III, m. 42°. 2-Chloropyrimidine (3.6 g.), 4.4 g. NaHSO₃, and 20 ml. H₂O heated 1 hr., evaporated, 2 g. KCN ground in, the mixture heated gently at 3 mm. to 260° in 20 min. then to 300° in 20 min., and maintained at 300° until nitrile distillation ceased gave 21% III. 4-Carbomethoxypyrimidine (X), m. 70-1°, was obtained in 47, 52, or 100% yields from the free acid and MeOH-H₂SO₄, MeOH-HCl, or CH₂N₂, resp. X was converted to 4-carbamoylpyrimidine (XI), m. 197°. XI (5.0 g.) stirred 20 hrs. with 30 ml. POCl₃, refluxed 1 hr. at 135-40°, and extracted similarly to I gave 77% 4-cyanopyrimidine (XII), m. 31°. 5-Cyanopyrimidine (XIII), could not be obtained by reductive diazotization of 4-amino-5-cyanopyrimidine. 5-Carboxypyrimidine (XIV) (25 g.) in 200 ml. Et₂O treated at 0° with half of a 1250 ml. Et₂O solution of CH₂N₂ from 75 g. MeN(NO)CONH₂ and 25 g. addnl. XIV added alternately with the rest of the CH₂N₂ gave after 19 hrs. 100% 5-carbomethoxypyrimidine, m. 84°, converted to XIII, m. 85-6°, via 5-carbamoylpyrimidine, m. 214°. Pyrazinamide (3 g.) and 15 ml. POCl₃ stirred 5 hrs., refluxed 40 min., and worked up gave 90% 2-cyanopyrazine (XV), b₇ 87°, m. 20°. Pyrazinoyl chloride (from pyrazinoic acid and SOCl₂, 1.3 hrs. reflux) and p-anisidine in C₆H₆ gave 2-[N-(4-methoxyphenyl)carbamoyl]pyrazine, m. 149-50°. Similarly prepared was 2-[N-(2-naphthyl)carbamoyl]pyrazine, m. 178-9°.

Ann. Chim. (Paris) published new progress about 92306-69-9. 92306-69-9 belongs to pyrimidines, auxiliary class Tetrazoles, name is 4-(1H-1,2,3,4-Tetrazol-5-yl)pyrimidine, and the molecular formula is C5H4N6, SDS of cas: 92306-69-9.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Sulkowska, A. published the artcilePhysical aspects of the interaction of pyrimidine and purine bases with proteins, COA of Formula: C5H6N2O2, the publication is Spectroscopy (Amsterdam, Netherlands) (2002), 16(3,4), 379-385, database is CAplus.

The study of complexation of purine and pyrimidine derivatives with two kind of serum albumin using ¹H NMR and spectrofluorescence technique are performed in order to obtain model interactions nucleic acid bases-protein. The order of binding strength is as follows: 5mC > 5mU(T) > 3mU > U for pyrimidines and N6mAde > N6Ado > 1mAde > ATP > Ado > Ade for adenine derivatives The effect of temperature on the hydrophobic interaction between the nitrogen bases and protein has been studied. The destabilization of protein structure causes loss of tertiary structural contacts, indicating that protein conformation is crucial for binding.

Spectroscopy (Amsterdam, Netherlands) published new progress about 608-34-4. 608-34-4 belongs to pyrimidines, auxiliary class Pyrimidine,Amide, name is 3-Methylpyrimidine-2,4(1H,3H)-dione, and the molecular formula is C6H12Br2, COA of Formula: C5H6N2O2.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Sulkowska, Anna published the artcileInteractions between pyrimidine bases derivatives and serum albumin in the presence of urea, Application of 3-Methylpyrimidine-2,4(1H,3H)-dione, the publication is Colloids and Surfaces, A: Physicochemical and Engineering Aspects (1999), 158(1-2), 151-156, database is CAplus.

A study of complex formation between pyrimidine base derivatives and serum albumin should allow us to determine the specificity of interactions of the pyrimidine derivatives with proteins. The role of the secondary and tertiary structure of serum albumin on the binding of the protein is also under investigation. The possible importance of the interactions between aliphatic residues of pyrimidine bases derivatives and serum albumin is discussed with respect to the problem of specific protein-nucleic acid interactions. The results suggest a release of ligands from their binding sites on the denatured polypeptide chain. The importance of hydrophobic interactions of the C5 Me group with hydrophobic grooves of protein in the presence of urea is suggested.

Colloids and Surfaces, A: Physicochemical and Engineering Aspects published new progress about 608-34-4. 608-34-4 belongs to pyrimidines, auxiliary class Pyrimidine,Amide, name is 3-Methylpyrimidine-2,4(1H,3H)-dione, and the molecular formula is C8H6KNO4S, Application of 3-Methylpyrimidine-2,4(1H,3H)-dione.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia