ChemInform Abstract: Reductive Cyclization of 6-Cyanomethyl-5-nitropyrimidines - An Efficient Route to 7-Alkyl-5H-pyrrolo(3,2-d)pyrimidines and 6-Amino-7, 7-dialkyl-7H-pyrrolo(3,2-d)pyrimidines. Utilization in the Synthesis of 9-Deaza Analogues of DHPA.
Abstract
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ChemInform Abstract
In the presence of Pd-C the nitropyrimidines (I) and (IV) undergo reductive cyclization to the 7-alkylpyrrolopyrimidines (II) and (V). The reaction with Na2S2O4 gives the intermediary derivatives (III) and (VI), respectively. The reductive cyclization can also be applied to prepare the pyrrolopyrimidine (VIII), an intermediate for the synthesis of 9-deaza analogues of DHPA. In this case, addition of AcOH is necessary for successful reaction.
