Sodium Carbonate → (S)-methyl 2-(2-chloro-6-vinylpyrimidine-4-carboxamido)propanoate

Participants

Reaction Conditions

Reaction Steps

To a mixture of (S)-methyl 2-(2,6-dichloropyrimidine-4-carboxamido)propanoate (0.921 g, 3.31 mmol) in dioxane (10 mL) was added 4,4,5,5-tetramethyl-2-vinyl-1,3,2-dioxaborolane (0.65 mL, 3.8 mmol), Na2CO3 (0,704 g, 6.64 mmol), and PdCl2(dppf) (0.142 g, 0.17 mmol). The reaction vessel was flushed with argon, sealed, and heated at 80° C. overnight. Additional 4,4,5,5-tetramethyl-2-vinyl-1,3,2-dioxaborolane (0.65 mL, 3.8 mmol) was added. After 7 hours at 80° C., additional 4,4,5,5-tetramethyl-2-vinyl-1,3,2-dioxaborolane (0.65 mL, 3.8 mmol) was added. After stirring at 80° C. for 4 more days the reaction was concentrated in vacuo to a residue and chromatographed over silica gel using 0-70% EtOAc in hexanes. The product fractions were evaporated in vacuo to give (S)-methyl 2-(2-chloro-6-vinylpyrimidine-4-carboxamido)propanoate as a yellow oil (0.444 g, 1.65 mmol, 50% yield). LC/MS: m/z=270.2 [M+H]+.

Provenance & Evidence