A General Regioselective Approach to 2,4-Disubstituted Pyrimidin-5-yl C-2-Deoxyribonucleosides

作者：Kubelka Tomas; Slavetinska Lenka; Hocek Michal^*

来源：Synthesis (Germany), 2012, 44(6): 953-965.

DOI：10.1055/s-0031-1289694

• nucleosides
• cross-coupling
• Heck reaction
• nucleophilic aromatic substitution
• regioselectivity

A new modular synthesis of diverse 2,4-disubstituted pyrimidin-5-yl C-2%26apos;-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.

• 出版日期2012-3