3-Deazaguanine, Dezaguanine, ICN-4221, 3-DG, NSC-261726, CI-809

地扎胍宁 地扎胍宁甲磺酸盐 Chemical Name: 6-Amino-1,5-dihydro-4H-imidazo[4,5-c]pyridin-4-one
CAS No. 41729-52-6, 87434-82-0 (mesylate)
项目整合开发状态: Phase III
项目研究机构: Valeant (Originator)
合成路线:Methyl-5-(4)-carbamoylmethylimidazole-4-(5)-carboxylate (I) and phosphoryl chloride are refluxed for 1 h,cooled,titurated with petroleum ether (30-60 C) and diethyl ether.Ice,followed by aqueous ammonia solution,is added to give a pH of 6.0.The solvent is then removed in vacuuo and the solid extracted with hot ethyl acetate.After drying with magnesium sulfate,the ethyl acetate is removed in vacuuo and the straw-colored methyl-5-(4)-cyanomethylimidazole-4-(5)-carboxylate (II) is recrystallized from water.Hydrazine hydrate is refluxed with (II),giving a precipitate of 5-amino-6-hydrazino-1,5-dihydroimidazol-[4,5-c]pyridin-4-one (III).A solution of (III) in boiling water is treated with Raney Nickel catalyst and refluxed.Filtration and concentration of the filtrate give,upon standing overnight,yellow crystals of 3-deazaguanine.