New efficient route to dissymmetric 2,4-di(het)aryl-pyrido[3,2-d]pyrimidines via regioselective cross-coupling reactions.
The first access to dissymmetric 2,4-di(het)aryl-pyrido[3,2-d]pyrimidines III is reported. Two mild alternative routes led to the rarely targeted compounds from 2,4-dichloro- and 2-chloro-4-isopropylsulfanyl-pyrido[3,2-d]pyrimidine 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. These results open the way to innovative synthesis strategies of various bis-functionalized pyrimidine series.
Tikad
Abdellatif
A
ICOA, UMR 6005, Centre National de la Recherche Scientifique, Université d'Orléans, Orléans, France.
Routier
Sylvain
S
Akssira
Mohamed
M
Leger
Jean-Michel
JM
Jarry
Christian
C
Guillaumet
Gérald
G
D003432:Cross-Linking Reagents / Q000737:chemistry*; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D015394:Molecular Structure; D011728:Pyridones / Q000737:chemistry*; D011743:Pyrimidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D003432:Cross-Linking Reagents; D011728:Pyridones; D011743:Pyrimidines; C030986:pyrimidine