Cesium fluoride → 4-(5-(1-Ethoxyvinyl)-2-fluoropyridin-3-YL)-6-methyl-1,3,5-triazin-2-amine

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-(5-chloro-2-fluoropyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine (273 mg, 1.14 mmol), X-Phos (50 mg, 0.11 mmol), diacetoxypalladium (24 mg, 0.11 mmol), cesium fluoride (519 mg, 3.42 mmol) and tributyl(1-ethoxyvinyl)stannane (0.54 mL, 1.60 mmol) in 1,4-dioxane (4 mL) and DMF (1 mL) was heated in a microwave at 120° C. for 1 h. The reaction mixture was passed through a short path of a neutral alumina column, eluted with 50 mL of DCM followed by 150 mL of EtOAc. The fractions containing the desired mass [m/z (ESI, positive ion) 276.0 (M+H)+] were collected and concentrated to give the title compound (203 mg, 64.7% yield) as an off white crystalline solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.60 (2H, m), 7.67 (2H, m), 4.93 (1H, d, J=3.1 Hz), 4.67 (1H, d, J=3.1 Hz), 3.95 (2H, m), 2.38 (3H, s), 1.11 (3H, m). m/z (ESI, positive ion) 276.0 (M+H)+.

Provenance & Evidence