With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.171887-03-9, name is N-(2-Amino-4,6-dichloropyrimidine-5-yl)formamide, molecular formula is C5H4Cl2N4O, molecular weight is 207.02, as common compound, the synthetic route is as follows.171887-03-9
Example A [00029] Preparation of (1S,4R)-cis-4-[2-amino-6-chloro-9H-purin-9-yl]-2-cyclopentene-1-methanol hydrochloride salt. [00030] A suspension of (1R,4S)-cis-[4-(hydroxymethyl)-2-cyclopentene-1-yl]carbamic acid, 1, 1-dimethylethyl ester (100 g) in industrial methylated spirit (IMS) (600 ml) was treated with concentrated hydrochloric acid (48 ml, 1.2 molar equivalents) and the resultant solution was heated to the boil over about 0.5 h. Heating under reflux was maintained for about 2.5 h. The solution was cooled to 20 to 25 C. and diluted with IMS (600 ml). Triethylamine (170 ml) was added followed by N-(2-amino-4,6-dichloro-5-pyrimidinyl)formamide (WO95/21161) (97 g). The suspension was heated under reflux for about 17 h to give a clear solution, which was cooled to 25 to 30 C. and finely divided potassium carbonate (169 g) was added. The suspension was stirred in this temperature range for about 0.5 h then cooled to 0 to 5 C. and the solids filtered off. The solids were washed with IMS (3¡Á180 ml and 1¡Á140 ml) and the combined filtrates and washings were concentrated under reduced pressure to a red gum. This was redissolved in IMS (1000 ml) and the solution was concentrated under reduced pressure to a gum. The dilution and re-concentration were repeated twice more, and the final gum was redissolved in IMS (350 ml). [00031] Meanwhile, a mixture of triethylorthoformate (900 ml) and tetrahydrofuran (THF) (400 ml) was prepared and cooled to 0 to 5 C. Concentrated hydrochloric acid (80 ml) was added, maintaininglthe temperature between 0 and 10 C., and more THF (100 ml,) was then added. To this mixture was added the IMS concentrate prepared above, which was rinsed in with IMS (100 ml). The mixture was warmed to 20 to 25 C. and seeded with authentic (1S,4R)-c-4-[2-amino-6-chloro-9H-purin-9-yl]-2-cyclopentene-1-methanol hydrochloride salt and stirring continued for about 20 h. The slurry was filtered, the solid was washed with a mixture of tert-butyl methyl ether and IMS (9/1, 3¡Á300 ml) and dried in vacuo at 40 to 45 C. to give the title compound (117 g, 82%) as a fawn coloured solid 1H-NMR (DMSO-d6)delta: 8.38(s, 1, purine CH), 7.50(br m, ca 5, NH3+, OH, HOD), 6.20(m, 1, CH) 5.94(m, 1, CH), 5.49(m, 1, NCH), 3.46(m, 2, OCH2), 2.91(br m, 1, CH), 2.70-2.60(m, 1, CH), 1.75-1.66(m, 1, CH).
Statistics shows that 171887-03-9 is playing an increasingly important role. we look forward to future research findings about N-(2-Amino-4,6-dichloropyrimidine-5-yl)formamide.
Reference:
Patent; SmithKline Beecham Corporation; US6646125; (2003); B1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia