Convenient synthesis of 2,4-disubstituted pyrido[2,3-d]pyrimidines via regioselective palladium-catalyzed reactions |
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Authors: | Yassine Riadi Stephane Massip Jean-Michel Leger Christian Jarry Saïd Lazar Gérald Guillaumet |
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Institution: | 1. Institut de Chimie Organique & Analytique, Université d’Orléans, UMR CNRS 7311, BP 6759, 45067 Orléans Cedex 2, France;2. Laboratoire de Biochimie, Environnement & Agroalimentaire, UARC 36, Université Hassan II Mohammedia-Casablanca, BP 146, 20650 Mohammedia, Morocco;3. Pharmacochimie, Université de Bordeaux, CNRS FRE 3396, 33000 Bordeaux, France |
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Abstract: | A novel and effective route for the synthesis of 2,4-disubstituted pyrido2,3-d]pyrimidines III is reported starting from the corresponding 2,4-dichloropyridopyrimidine 1 through regioselective functionalization palladium-catalyzed C–C coupling reactions, by two successive palladium-catalyzed reactions involving an original regioselective chlorine discrimination. Alternatively, type III compounds were elaborated from 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. |
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