合成路线:This compound can be obtained in two different ways:1) The reaction of 4,5,6-triaminopyrimidine (I) with refluxing SOCl2 gives 7-amino[1,2,5]thiadiazolo[3,4-d]pyrimidine (II).The reaction of 2-chloro-6-fluorobenzyl chloride (III) with ammonia in benzene affords 2-chloro-6-fluorobenzylamine (IV),which is condensed with (II) by heating at 150 C to yield 7-(2-chloro-6-fluorobenzyl)amino[1,2,5]thiadiazolo[3,4-d]pyrimidine (V).The formylation of (V) with formic acid in acetic anhydride gives 7-[N-formyl-N-(2-chloro-6-fluoro-benzyl)]amino[1,2,5]thiadiazolo[3,4-d]pyrimidine (VI),which by desulfuration with Raney-Ni in ethanol - water gives 4-[N-formyl-N-(2-chloro-6-fluorobenzyl)]amino-5,6-diaminopyrimidine (VII),product not isolated that dehydrates spontaneously to arprinocid.
参考文献标题:New synthesis of a 9-substituted adenine
文献作者:Hartman,G.D.
参考来源:J Org Chem 1978,43(5),960-962
合成路线:This compound can be obtained in two different ways:1) The reaction of 4,5,6-triaminopyrimidine (I) with refluxing SOCl2 gives 7-amino[1,2,5]thiadiazolo[3,4-d]pyrimidine (II).The reaction of 2-chloro-6-fluorobenzyl chloride (III) with ammonia in benzene affords 2-chloro-6-fluorobenzylamine (IV),which is condensed with (II) by heating at 150 C to yield 7-(2-chloro-6-fluorobenzyl)amino[1,2,5]thiadiazolo[3,4-d]pyrimidine (V).The formylation of (V) with formic acid in acetic anhydride gives 7-[N-formyl-N-(2-chloro-6-fluoro-benzyl)]amino[1,2,5]thiadiazolo[3,4-d]pyrimidine (VI),which by desulfuration with Raney-Ni in ethanol - water gives 4-[N-formyl-N-(2-chloro-6-fluorobenzyl)]amino-5,6-diaminopyrimidine (VII),product not isolated that dehydrates spontaneously to arprinocid.
合成路线:2) By condensation of 2-chloro-6-fluorobenzyl chloride (III) with adenine (VIII) by means of Aliquat 336 in hexane - water,acetone or hexamethyl phosphoramide.
参考文献标题:Arprinocid
文献作者:Blancafort,P.; Serradell,M.N.; Castar,J.; Leeson,P.A.; Mealy,N.E.
参考来源:Drugs Fut 1980,5(7),332
产品链接: CAS No. 55779-18-5››