Cesium fluoride → 6-(5-(1-Ethoxyvinyl)-2-fluoropyridin-3-yl)-2-methylpyrimidin-4-amine

Participants

Reaction Conditions

Reaction Steps

To a 5 mL microwave reaction tube was added 6-(5-chloro-2-fluoropyridin-3-yl)-2-methylpyrimidin-4-amine (227 mg, 0.95 mmol), palladium acetate (10 mg, 0.048 mmol), X-phos (40 mg, 0.09 mmol), cesium fluoride (433 mg, 2.85 mmol) and tributyl(1-ethoxyvinyl)stannane (0.45 mL, 1.33 mmol) in 1,4-dioxane (4 mL) and DMF (1 mL). The glass tube was sealed and heated in a microwave at 120° C. for 1 h. The reaction mixture was passed through a short path of neutral alumina column, eluted with 50 mL of DCM followed by 150 mL of EtOAc and 50 mL of 5% MeOH in EtOAc. The desired fractions were collected, concentrated to give 6-(5-(1-ethoxyvinyl)-2-fluoropyridin-3-yl)-2-methylpyrimidin-4-amine (208 mg, 80% yield) as an off white crystalline solid. m/z (ESI, positive ion) 275.1 (M+H)+.

Provenance & Evidence