Convenient synthesis of 2,4-disubstituted pyrido[2,3-d]pyrimidines via regioselective palladium-catalyzed reactions

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• 作者：Yassine Riadi^a ; ^b ; Stephane Massip^c ; Jean-Michel Leger^c ; Christian Jarry^c ; Saï ; d Lazar^b ; Gé ; rald Guillaumet^a ; ^{gerald.guillaumet@univ-orleans.fr}
• 关键词：Pyrido[2 ; 3-d]pyrimidines ; Suzuki&ndash ; Miyaura ; Cross-coupling ; Palladium-catalyzed
• 刊名：Tetrahedron
• 出版年：2012
• 期刊代码：107_00404020
• 类别：ch
• 出版时间：24 June, 2012
• 卷：68
• 期：25
• 页码：5018-5024
• 文件大小：2726 K

摘要

A novel and effective route for the synthesis of 2,4-disubstituted pyrido[2,3-d]pyrimidines dFont">III is reported starting from the corresponding 2,4-dichloropyridopyrimidine dFont">1 through regioselective functionalization palladium-catalyzed C-C coupling reactions, by two successive palladium-catalyzed reactions involving an original regioselective chlorine discrimination. Alternatively, type dFont">III compounds were elaborated from dFont">2 by C-2 chlorine further displacement of the C-4 isopropylsulfanyl group, which acted as a temporary C-4 protecting group. Further Suzuki-Miyaura cross-coupling reactions led to C-2 and C-4 disubstituted compounds.