Abstract
N-9-Substituted 2,8-diaminopurines 7 were prepared in several steps starting from aldehyde 1 anchored on the resin. Thus, the resin-bound secondary amines 2 were obtained via reductive alkylation of primary amines (R1NH2) with 1 using Na(OAc)3BH. N-Arylation of amines 2 with 8, followed by the reduction of nitro group of the resulting resin-bound 5-nitro-pyrimidines 3 with Na2S4O4, gave triaminopyrimidines 4. Alkyl thioureas 5 were obtained via the reaction of 4 with alkyl isothiocyanates and subsequently transformed into 6 using DIC in DMF-EtOH. After TFA-mediated cleavage from the solid support, the 8-alkyl diaminopurines 7a-c were obtained in 54-89% yield with 77-88% purity.
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