Journal
TETRAHEDRON
Volume 64, Issue 8, Pages 1778-1785Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2007.11.101
Keywords
nucleobase; alcohol; N-alkylation; N-(p-toluenesulfonyl)imidazole (TsIm); triethylamine; K2CO3
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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. (C) 2007 Elsevier Ltd. All rights reserved.
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