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