Sodium Carbonate → 4-(difluoromethyl)-N-(3-methyl-5-(1-(3-methylbut-3-en-2-yl)-1H-pyrazol-4-yl)phenyl)pyrimidin-2-amine

Participants

Reaction Conditions

Reaction Steps

4-(Difluoromethyl)-N-(3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidin-2-amine (400 mg, 1.11 mmol) and 4-bromo-1-(3-methylbut-3-en-2-yl)-1H-pyrazole (238 mg, 1.11 mmol) were dissolved in dioxane (4 ml) and degassed with nitrogen for 5 minutes. PdCl2(dppf)-CH2Cl2 (90 mg, 0.11 mmol) and sodium carbonate (2.0 M in water, 1.1 ml, 2.2 mmol) were added and the reaction was sealed and heated to 90° C. for 12 hours. The reaction was cooled, diluted with water (10 mL), and the product was extracted with ethyl acetate (2×20 mL). The extracts were dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to afford the crude product residue. The crude product residue was purified by column chromatography on silica two times utilizing (10-50% ethyl acetate/hexanes) and (0-5% acetone/dichloromethane) to afford 4-(difluoromethyl)-N-(3-methyl-5-(1-(3-methylbut-3-en-2-yl)-1H-pyrazol-4-yl)phenyl)pyrimidin-2-amine. MS ESI calcd. for C20H22F2N5 [M+H]+ 370. found 370.

Provenance & Evidence