Synthesis of 6-alkyluridines from 6-cyanouridine via zinc (II) chloride-catalyzed nucleophilic substitution with alkyl grignard reagents

…, YY Yang, CC Lin, TC Chien

Index: Shih, Yu-Chiao; Yang, Ya-Ying; Lin, Chun-Chi; Chien, Tun-Cheng Journal of Organic Chemistry, 2013 , vol. 78, # 8 p. 4027 - 4036

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Citation Number: 6

Abstract

6-Cyanouracil derivatives underwent a direct nucleophilic substitution reaction with alkyl Grignard reagents in the presence of zinc (II) chloride as a catalyst to form the corresponding 6-alkyluracils. This methodology is applicable to sugar-protected 6-cyanouridine and 6- cyano-2′-deoxyuridine without the protection at the N 3-imide and provides a facile and general access to versatile 6-alkyluracil and 6-alkyluridine derivatives.

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