One-pot synthesis of N-alkyl purine and pyrimidine derivatives from alcohols using TsIm: a rapid entry into carboacyclic nucleoside synthesis

MNS Rad, A Khalafi-Nezhad, S Behrouz, MA Faghihi…

Index: Soltani Rad, Mohammad Navid; Khalafi-Nezhad, Ali; Behrouz, Somayeh; Faghihi, Mohammad Ali; Zare, Abdolkarim; Parhami, Abolfath Tetrahedron, 2008 , vol. 64, # 8 p. 1778 - 1785

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Citation Number: 24

Abstract

A convenient and efficient one-pot N-alkylation of nucleobases from alcohols using N-(p- toluenesulfonyl) imidazole (TsIm) is described. In this method, treatment of alcohols with a mixture of purine or pyrimidine nucleobase, TsIm, K2CO3, and triethylamine in refluxing DMF regioselectively furnishes the corresponding N-alkyl nucleobases in good yields. This methodology is highly efficient for various structurally diverse primary alcohols.