Exploitation of a new route to fused pyrroles: Synthesis of TNP-351, homo-MTA and 5-arylpyrrolo[2,3-d]pyrimidines

We have developed a new methodology for the construction of pyrrolo[2,3-d]p yrimidines that involves Michael addition of 2,6-diamino-4(3 (H) under bar) -pyrimidinone or 2,4,6-triaminopyrimidines to nitroolefins, followed by a N ef reaction of the resulting adduct to form an intermediate aldehyde that s pontaneously cyclizes to the fused pyrrole ring, This methodology has been exploited in a new synthesis of TNP-351, and for the first reported prepara tion of homo-MTA and of a series of 5-arylpyrrolo[2,3-(d) under bar]pyrimid ines. (C) 1999 Elsevier Science Ltd. All rights reserved.