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

Article abstract of DOI:10.1016/S0040-4039(99)00677-2

We have developed a new methodology for the construction of pyrrolo[2,3- d]pyrimidines that involves Michael addition of 2,6-diamino-4(3H)- pyrimidinone or 2,4,6-triaminopyrimidines to nitroolefins, followed by a Nef reaction of the resulting adduct to form an intermediate aldehyde that spontaneously cyclizes to the fused pyrrole ring. This methodology has been exploited in a new synthesis of TNP-351, and for the first reported preparation of homo-MTA and of a series of 5-arylpyrrolo[2,3-d]pyrimidines.