MICROWAVE-ASSISTED N-ALLYLATION OF URACIL AND THYMINE PYRIMIDINIC BASES

Abstract

This work presents a new synthetic approach to N(1)-allylation of pyrimidine nucleobases with allyl bromide. The increased efficiency of the proposed method is based on two specific elements: (a) the nucleoside N-deprotonation is carried out in a homogeneous system by using sodium methylsulfinylmethylide in DMSO; (b) the allylation reaction is microwave-assisted. This method ensures high yields (87–88%) of the monoallylated products, short reaction time (1.5 h as compared to tens of hours for classical methods), and provides protection against side-reactions. NMR analysis of the crude reaction mixture indicated a ratio of 6–8 : 1 between N(1)-allyl derivatives and N(1),N(3)-diallyl derivatives.

Also published in Chemistry of Heterocyclic Compounds, 2011, 47 (5), pp 602-606

http://link.springer.com/article/10.1007/s10593-011-0804-2