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Synlett 2011(8): 1179-1183  
DOI: 10.1055/s-0030-1259954
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Copper(II)-Catalyzed Synthesis of Pyrimidines from Propargylic Alcohols and Amidine: A Propargylation-Cyclization-Oxidation Tandem Reaction

Min Lin, Qing-zhen Chen, Yu Zhu, Xin-liang Chen, Ji-jun Cai, Ying-ming Pan, Zhuang-ping Zhan*
Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005 Fujian, P. R. of China
Fax: +86(592)2180318; e-Mail: zpzhan@xmu.edu.cn;
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Publication History

Received 31 December 2010
Publication Date:
18 April 2011 (online)

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Abstract

A new approach to the tandem synthesis of 2,4-disubstituted or 2,4,6-trisubstituted pyrimidines from propargylic alcohols with amidine is described. This reaction is catalyzed by 20 mol% Cu(OTf)2 to give pyrimidines in moderate to good yields via a propargylation-cyclization-oxidation tandem sequence.

Key words

pyrimidine - propargylation - amidine - copper - annulation

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7

General Procedure for the Synthesis of Substituted Pyrimidines
To a solution of propargylic alcohol 1 (0.5 mmol) and amidine 2 (1 mmol) in PhCl (2 mL), Cu(OTf)2 (0.1 mmol) was added, and it was stirred at reflux. When the reaction was completed (monitored by TLC), the solvent was removed under vacuum, and then the residue was further purified by silica gel column chromatography (PE and EtOAc) to afford pyrimidine.