Tag: M.W=100-150

Mussetta, Marie T. published the artcileConfigurations of 4-amino- and of 4-acetylaminopyrimidines and their derivatives, Safety of N,N-Dimethylpyrimidin-4-amine, the publication is Comptes Rendus des Seances de l’Academie des Sciences, Serie C: Sciences Chimiques (1973), 277(24), 1279-82, database is CAplus.

Dipole moments for pyrimidine, 4-aminopyrimidine (I), and 9 N-substituted I were measured in benzene or dioxane and were interpreted in relation to preferential conformations and interactions between the amino and adjacent ring N atoms.

Comptes Rendus des Seances de l’Academie des Sciences, Serie C: Sciences Chimiques 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, Safety of N,N-Dimethylpyrimidin-4-amine.

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

Kolli, Murali Krishna published the artcilePd-PEPPSI-IPent^Cl: a new highly efficient ligand-free and recyclable catalyst system for the synthesis of 2-substituted indoles via domino copper-free Sonogashira coupling/cyclization, Synthetic Route of 1059705-07-5, the publication is New Journal of Chemistry (2017), 41(16), 8187-8195, database is CAplus.

A pyridine-containing decidedly resourceful Pd-N-heterocyclic carbene complex, Pd-PEPPSI-IPentCl (PEPPSI = pyridine enhanced precatalyst preparation, stabilization, and initiation), prepared and used as a first class recyclable catalytic system for the synthesis of 2-substituted indoles I [X = H, Boc; R¹ = H, 5-OMe, 6-i-Pr, 6-Cl, 5-NO₂, 5,7-di-NO₂; R² = Ph, 4-ClC₆H₄, 2-naphthyl, pyrimidin-5-yl, etc.] via domino copper-free Sonogashira coupling/cyclization. The catalyst showed a greater performance in the cascade reaction of various 2-bromo anilines with different terminal aromatic acetylenes under mild (60 °C) and green conditions (ethanol:water) even in the absence of a copper catalyst and an inert atm. It was confirmed that 0.1 mol% of the catalyst was sufficient, recyclable and could be reused up to six cycles.

New Journal of Chemistry published new progress about 1059705-07-5. 1059705-07-5 belongs to pyrimidines, auxiliary class Pyrimidine, name is 5-Ethynyl-2-methoxypyrimidine, and the molecular formula is C7H6N2O, Synthetic Route of 1059705-07-5.

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

Yekeler, Huelya published the artcileProtomeric tautomerisms of N-methylated pyrimidine bases, Synthetic Route of 608-34-4, the publication is Journal of Molecular Structure: THEOCHEM (2005), 713(1-3), 201-206, database is CAplus.

Tautomerisms of N1-Me, N3-Me, and N1, N3-dimethyl derivatives of uracil, 5-fluorouracil and thymine have been examined in the gas phase and in water. Geometry optimizations were carried out at the HF/6-31G**, HF/6-31+G** and B3LYP/6-31+G** levels. Also, single-point MP2/6-31+G** calculations were performed on the HF/6-31+G** optimized geometries. The influence of the solvent was examined from the self-consistent reaction field (SCRF) calculations Analyzing the results, only attachment of fluorine atom at position 5 of N1-Me uracil changes the order of the stabilities of the tautomers.

Journal of Molecular Structure: THEOCHEM 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 C21H37BO, Synthetic Route of 608-34-4.

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

Qiu, Yan published the artcileDiscovery of uracil derivatives as potent inhibitors of fatty acid amide hydrolase, Application of 3-Methylpyrimidine-2,4(1H,3H)-dione, the publication is Molecules (2016), 21(2), 229/1-229/11, database is CAplus and MEDLINE.

Fatty Acid Amide Hydrolase (FAAH) is an intracellular serine enzyme involved in the biol. degradation of the fatty acid ethanolamide family of signaling lipids, which exerts neuroprotective, anti-inflammatory, and analgesic properties. In the present study, a conjugated 2,4-dioxo-pyrimidine-1-carboxamide scaffold was confirmed as a novel template for FAAH inhibitors, based on which, a series of analogs had been prepared for an initial structure-activity relationship (SAR) study. Most of the synthesized compounds displayed moderate to significant FAAH inhibitory potency. Among them, compounds 11 and 14 showed better activity than others, with IC₅₀ values of 21 and 53 nM. SAR anal. indicated that 2,4-dioxopyrimidine-1-carboxamides represented a novel class of potent inhibitors of FAAH, and substitution at the uracil ring or replacement of the N-terminal group might favor the inhibitory potency. Selected compounds of this class may be used as useful parent mols. for further investigation.

Molecules 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, Application of 3-Methylpyrimidine-2,4(1H,3H)-dione.

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

Lv, Jing-Hui published the artcileMellitic acid production by ruthenium ion-catalyzed oxidation of cokes, Computed Properties of 608-34-4, the publication is Journal of Cleaner Production (2021), 124828, database is CAplus.

Cokes are rich in highly condensed aromatic rings, however, the current applications of cokes mainly focus on the thermal energy or carbon-rich structures, and the aromatic ring structures in cokes are underutilized, which are usually employed as feedstock to fabricate valuable fine chems. and synthesized with complex steps. The pyrolysis temperatures have great impact on the structures of resulting cokes. It is necessary to learn about the structural features of cokes produced from different pyrolysis conditions to explore the optimal reaction conditions. This study reported an eco-friendly and efficient method, ruthenium ion-catalyzed oxidation, to utilize Guizhou cokes produced from different pyrolysis temperatures for green and value-added chem. production The results indicate that arenecarboxylic acids account for more than 90% of all the oxidation products, in which mellitic acid could be up to more than 70%. Compared with previous studies, this is the highest mellitic acid yield achieved in the oxidation products of fossil resources, indicating that cokes show good performance for the clean production of mellitic acid. The ruthenium ion-catalyzed oxidation product distribution demonstrates that 1,200 °C is a turning point during coking of Guizhou coals and the structure and reactivity of Guizhou coke_1,200 deviate from the expected variation tendency, which is related to the inverse influence of pyrolysis temperatures on condensation degree and ash property of cokes. Effect of pyrolysis temperatures on aromatic structures and reactivity of Guizhou cokes was also discussed further.

Journal of Cleaner Production 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, Computed Properties of 608-34-4.

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