A regioselective approach to trisubstituted 2 (or 6)-arylaminopyrimidine-5-carbaldehydes and their application in the synthesis of structurally and electronically unique GlambdaC base precursors

The Journal of Organic Chemistry
Rachel L BeingessnerHicham Fenniri

Abstract

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.

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Citations

Aug 18, 2010·Chemical Communications : Chem Comm·Gabor BorzsonyiHicham Fenniri
Apr 26, 2012·Tissue Engineering. Part a·Linlin SunThomas J Webster
Oct 12, 2010·The Journal of Organic Chemistry·Gabor BorzsonyiHicham Fenniri
Oct 13, 2010·Journal of the American Chemical Society·Gabor BorzsonyiHicham Fenniri
Jul 11, 2013·The Journal of Organic Chemistry·Marcin JasińskiPiotr Kaszyński
Sep 2, 2010·Journal of Combinatorial Chemistry·P Jake SlavishThomas R Webb
Aug 14, 2018·The Journal of Organic Chemistry·Neil A StrotmanJoerg Deerberg
Jan 9, 2020·Journal of the American Chemical Society·Prabhat TripathiMeni Wanunu

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