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Synthesis of 6‑Alkyluridines from 6‑Cyanouridine via Zinc(II) Chloride-Catalyzed Nucleophilic Substitution with Alkyl Grignard Reagents

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posted on 19.04.2013, 00:00 by Yu-Chiao Shih, Ya-Ying Yang, Chun-Chi Lin, Tun-Cheng Chien
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 N3-imide and provides a facile and general access to versatile 6-alkyluracil and 6-alkyluridine derivatives.

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