Beingessner Rachel L, Deng Bo-Liang, Fanwick Phillip E, Fenniri Hicham
National Institute for Nanotechnology and Department of Chemistry, University of Alberta, 11421 Saskatchewan Drive, Edmonton, Alberta, T6G 2M9, Canada.
J Org Chem. 2008 Feb 1;73(3):931-9. doi: 10.1021/jo7021422. Epub 2008 Jan 8.
An efficient regioselective synthesis of trisubstituted 2(or 6)-arylaminopyrimidine-5-carbaldehydes has been developed via an S(N)Ar reaction of 2,4,6-trichloropyrimidine-5-carbaldehyde with aniline, methylamine, and alkoxide nucleophiles using a combination of phase-transfer catalysis and more traditional SNAr reaction conditions. We demonstrate that in a few synthetic steps, highly functionalized fused-bicyclic pyrimidine substrates can be accessed from the trisubstituted 2-arylaminopyrimidine-5-carbaldehydes. Furthermore, these fused-bicyclic compounds are readily derivatized using the Suzuki cross-coupling reaction to generate electronically and structurally unique GlambdaC base precursors.
通过2,4,6-三氯嘧啶-5-甲醛与苯胺、甲胺和醇盐亲核试剂的S(N)Ar反应，利用相转移催化和更传统的SNAr反应条件的组合，开发了一种高效的区域选择性合成三取代2（或6）-芳基氨基嘧啶-5-甲醛的方法。我们证明，在几个合成步骤中，可以从三取代的2-芳基氨基嘧啶-5-甲醛获得高度官能化的稠合双环嘧啶底物。此外，这些稠合双环化合物很容易通过铃木交叉偶联反应进行衍生化，以生成电子和结构独特的GλC碱基前体。
