Mild Iodine−Magnesium Exchange of Iodoaromatics Bearing a Pyrimidine Ring with Isopropylmagnesium Chloride

Xiao-jun Wang,* Yibo Xu, Li Zhang, Dhileepkumar Krishnamurthy, and Chris H. Senanayake
Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals Inc., Ridgefield, Connecticut 06877
Org. Lett., 2006, 8 (14), pp 3141–3144
DOI: 10.1021/ol061156s
Publication Date (Web): June 17, 2006
Copyright © 2006 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, xwang@rdg.boehringer-ingelheim.com

Abstract

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Iodoaromatics bearing a reactive pyrimidine ring underwent a clean iodine−magnesium exchange with isopropylmagnesium chloride in the presence of bis[2-(N,N-dimethylamino)ethyl] ether to provide the corresponding Grignard reagents. The presence of bis[2-(N,N-dimethylamino)ethyl] ether prevented reduction of the pyrimidine ring and addition by isopropylmagnesium chloride. As a result, the newly formed reactive Grignard reagents were allowed to react with electrophiles in a highly selective manner to afford adducts in excellent yields.

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History

  • Published In Issue July 06, 2006
  • Received May 11, 2006

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