Water → 4-(2-(5-Fluoro-6-methoxypyridin-3-ylamino)-5-(2-methylprop-1-enyl)pyridin-3-YL)-6-methyl-1,3,5-triazin-2-amine

Participants

Reaction Conditions

Reaction Steps

To 4-(5-chloro-2-(5-fluoro-6-methoxypyridin-3-ylamino)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine (0.85 g, 2.350 mmol) was added dioxane (23.50 mL), potassium carbonate in water (3.52 mL, 7.05 mmol), 4,4,5,5-tetramethyl-2-(2-methylprop-1-enyl)-1,3,2-dioxaborolane (0.723 mL, 3.52 mmol) (Frontier Scientific), and bis-(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (Aldrich; 0.083 g, 0.117 mmol). The resulting mixture was sparged with nitrogen and then stirred at 80° C. for 16 h. The reaction mixture was subsequently diluted with 150 mL of EtOAc, added to a separatory funnel, partitioned with sodium bicarbonate (saturated, aqueous), washed 2 times with 150 mL of sodium bicarbonate (saturated, aqueous), separated, dried over sodium sulfate, and concentrated in vacuo. Chromatographic purification of the residue (silica gel, 0% to 100% EtOAc/hexanes) gave the title compound (88% yield) as a yellow solid. m/z (ESI, +ve ion) 382.2 (M+H)+.

Provenance & Evidence