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Communication | Special issue | Vol 82, No. 2, 2010, pp.1137-1141
Published online, 16th August, 2010
DOI: 10.3987/COM-10-S(E)89
Hexamethyldisilazane-Promoted Sonogashira Reaction of Polyfunctionalized N-Containing Heterocycles

Masahiko Inouye,* Yasuhiro Doi, Junichi Azuchi, Wataru Shirato, Junya Chiba, and Hajime Abe*

*Laboratory of Chemical Biology, Faculty of Pharmaceutical Sciences, Toyama University, 2630 Sugitani, Toyama 930-0194, Japan

Abstract

1,1,1,3,3,3-Hexamethyldisilazane (HMDS) was found to be an efficient solvent for Sonogashira reaction. For the synthesis of C-nucleosides, Sonogashira reaction of ethynyldeoxyriboside with halogenated pyrimidine or pyridine derivatives could be improved by the use of an HMDS−DMF mixed solvent. In situ protection of hydroxy and amino groups by the solvent system may play an important role for the improvement.