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Synthesis 2012(6): 953-965
DOI: 10.1055/s-0031-1289694
DOI: 10.1055/s-0031-1289694
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkA General Regioselective Approach to 2,4-Disubstituted Pyrimidin-5-yl C-2-Deoxyribonucleosides
Further Information
Received
9 December 2011
Publication Date:
06 February 2012 (online)
Publication History
Publication Date:
06 February 2012 (online)
Abstract
A new modular synthesis of diverse 2,4-disubstituted pyrimidin-5-yl C-2′-deoxyribonucleosides by sequential regioselective reactions of 2,6-dichloropyrimidin-5-yl C-nucleoside was developed. The intermediate was prepared by the Heck coupling of 2,6-dichloro-5-iodopyrimidine with glycal followed by desilylation and reduction. Its mild nucleophilic substitutions or cross-coupling reactions proceeded regioselectively at position 4, while at elevated temperatures or with excess reagent, a double substitution occurred. The 2-chloro-4-substituted intermediates underwent another substitution or coupling to afford a two-dimensional library of diverse 2,4-disubstituted pyrimidin-5-yl C-2-deoxyribonucleotides.
Key words
nucleosides - cross-coupling - Heck reaction - nucleophilic aromatic substitution - regioselectivity
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