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Synfacts 2006(4): 0325-0325
DOI: 10.1055/s-2006-932075
DOI: 10.1055/s-2006-932075
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York
Sonogashira-Mediated Synthesis of 4-Aryl-5-Pyrimidinylimidazoles
X. Deng, N. S. Mani*
Johnson & Johnson Pharmaceutical Research & Development, San Diego, USA
Further Information
Publication History
Publication Date:
24 March 2006 (online)
Significance
A new and efficient route to 4-aryl-5-pyrimidinylimidazoles 4 starting from 2,4-dichloropyrimidine (1) and TMS-acetylene is reported. Intermediates 2, obtained by two Sonogashira coupling reactions in good yields and without column chromatography, are subjected to KMnO4 oxidation to afford 1,2-diketones 3 which, upon the cyclocondensation with aldehydes in the presence of ammonium acetate, furnish the target products 4 in good overall yields. The scope and limitations of the method were not widely tested.