Synthesis 2007(24): 3915-3922  
DOI: 10.1055/s-2007-983885
PSP
© Georg Thieme Verlag Stuttgart · New York

Preparation of Polyfunctionalized 2,6-Dimethoxypyrimidine Derivatives via Chemo- and Regioselective Direct Zinc Insertion

Darunee Soorukram, Nadège Boudet, Vladimir Malakhov, Paul Knochel*
Department Chemie und Biochemie, Ludwig-Maximilians-Universität München, Butenandtstraße 5-13, Haus F, 81377 München, Germany
Fax: +49(89)218077680; e-Mail: [email protected];
Further Information

Publication History

Received 5 April 2007
Publication Date:
29 August 2007 (online)

Abstract

The functionalization at the C4 and/or C5 positions of 2,6-dimethoxypyrimidine derivatives via direct chemo- and regioselective zinc insertions is described. The insertion of commercially available zinc dust into C-I and C-Br bonds, in the presence of LiCl, proceeded under mild reaction conditions. The reactions of the resulting organozinc reagents with electrophiles gave the expected products in good yields. This procedure represents a new method for the polyfunctionalization of uracil derivatives.

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Conversion >98%; the reaction conversion was monitored by GC-analysis of hydrolyzed reaction aliquots quenched with aq NH4Cl.

14

Boudet, N. The preparation of this starting material will be published soon elsewhere.