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Synthesis 2008(22): 3697-3702  
DOI: 10.1055/s-0028-1083208
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© Georg Thieme Verlag Stuttgart ˙ New York

Multiple Regio- and Chemoselective Functionalizations of Pyrimidine Derivatives Using TMPMgCl×LiCl and TMP2Mg×2 LiCl

Marc Mosrin, Marilena Petrera, Paul Knochel*
Department Chemie und Biochemie, Ludwig-Maximilians-Universität München, Butenandtstrasse 5-13, Haus F, 81377 München, Germany
Fax: +49(89)218077680; e-Mail: paul.knochel@cup.uni-muenchen.de;
Further Information

Publication History

Received 21 July 2008
Publication Date:
23 October 2008 (online)

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Abstract

The multiple successive regio- and chemoselective magnesiation of commercially available 2-bromopyrimidine at the C4, C6, and C5 positions allows the regioselective functionalization of all positions of the pyrimidine ring.

Key words

Grignard reagents - pyrimidines - regioselective magnesiation - magnesium bases

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2-Bromopyrimidine is commercially available from Acros, Aldrich, Fluka (ca $15 for 1 g).