Parallel solution-phase synthesis of a 2,6,8,9-tetrasubstituted purine library via a sulfur intermediate.

摘要: Purine analogues exhibiting a wide range of pharmacological activities have been considered privileged structure in medicinal chemistry. In addition, the purine core consisting four points structural diversity is well-sought scaffold combinatorial Although most efforts focused on 2,6,9-, 6,8,9-, or 2,8,9-trisubstituted purines, syntheses 2,6,8,9-tetrasubstituted purines are rare. This paper presents parallel solution phase approach for synthesis fully substituted via 6-sulfur-substituted pyrimidine as key intermediate. strategy combining construction and modification ring thus increases final products. Sequential substitution chlorines 4,6-dichloro-2-methyl-5-nitropyrimidine with primary amine benzylmercaptan afforded 4-(substituted)amino-6-benzylthio-5-nitropyrimidine, which was readily converted to its diaminopyrimidine analogue by reduction nitro group. The diaminop...