Effects of Various Bases on Acid-Catalyzed Amination of 2-Chloro-5-ethylpyrimidine: Synthesis of PPARpan Agonist GW693085

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• 作者：Bobby N. Glover ; Lynda A. Jones ; Byron ; S. Johnson ; Alan Millar ; Martin H. Osterhout ; Shiping Xie
• 刊名：Journal of Organic Chemistry
• 出版年：2010
• 出版时间：June 4, 2010
• 年：2010
• 卷：75
• 期：11
• 页码：3904-3907
• 全文大小：736K
• 年卷期：v.75,no.11(June 4, 2010)
• ISSN：1520-6904

文摘

A unique buffering effect of various bases, i-Pr₂NEt and CaCO₃ in particular, was observed for the acid-catalyzed chloro displacement of 2-chloro-5-ethylpyrimidine with a 2-methyl-2-phenylpropanamine. The use of the carefully chosen bases was essential for the progression of the chloro displacement as well as the stability of the product in the presence of HCl formed. Research work leading to an efficient synthesis of PPARpan agonist GW693085 is described, featuring highly selective sequential N- and O-alkylations.