Clifton E. Hyman

Solid phase synthesis of 1,3,5-trisubstituted pyridin-2-ones

Abstract The solid phase synthesis of 1,3,5-trisubsituted pyridin-2-ones is reported via selective 1 NH- alkylation of 3-amino-5-carbomethoxy-1 H -pyridin-2-one with a solid-supported halo-acid. Coupling of an acid to solid-supported 3-aminopyridinone was followed by saponification of the methyl ester to give the acid. Activation of the acid via the pentafluorophenyl ester allowed reaction with an amine, and cleavage from the solid support with TFA:H 2 O (95:5) provided 1,3,5-trisubstituted pyridin-2-ones.