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Synthesis 2012(1): 120-124  
DOI: 10.1055/s-0031-1289615
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Unusual Regioselective Reactions of 2,4-Bis(methylsulfanyl)pyrimidine under Modified Suzuki and Stille Cross-Coupling Conditions

Abdelbasset A. Farahata,b, David W. Boykin*a
a Department of Chemistry, Georgia State University, Atlanta, GA 30303, USA
Fax: +1(404)4135505; e-Mail: dboykin@gsu.edu;
b Department of Pharmaceutical Organic Chemistry, Faculty of Pharmacy, Mansoura University, Mansoura 35516, Egypt
Further Information

Publication History

Received 15 September 2011
Publication Date:
22 November 2011 (online)

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Abstract

2,4-Bis(methylsulfanyl)pyrimidine undergoes unusual regioselective cross-coupling reactions with aryl boronic acids and organostannanes in the presence of copper(I) 3-methylsalicylate or copper(I) thiophene-2-carboxylate as a cofactor to give 2-aryl-4-(methylsulfanyl)pyrimidines as the major products. The structures of the products of the coupling reaction were established by X-ray crystallography.

Key words

coupling reactions - cross-coupling - regioselectivity - heterocycles - catalysis - Stille reaction

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