Potassium Phosphate, Tribasic → 7-(1-isopropyl-1H-pyrazol-4-yl)-5-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine

Participants

Reaction Conditions

Reaction Steps

To a flask charged with 7-chloro-5-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine (Preparation G; 0.200 g, 0.572 mmol), 1-isopropyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.202 g, 0.857 mmol) (Table 2, compound a), and potassium phosphate (0.857 mL, 1.71 mmol) was added 5 mL of Dioxane and argon was bubbled through for 10 minutes before dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (0.0545 g, 0.114 mmol) and tris(dibenzylideneacetone)dipalladium (0.0523 g, 0.0572 mmol) were added quickly and argon was bubbled through the reaction for 10 minutes before it was sealed and heated to 65° C. overnight. The reaction was diluted with ethyl acetate (100 mL) and washed with aqueous saturated sodium bicarbonate (40 mL) and brine (40 mL). The organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure. The crude was purified by silica gel column chromatography, eluting with a mixture of ethyl acetate and 0.5% ammonium hydroxide to afford 7-(1-isopropyl-1H-pyrazol-4-yl)-5-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine (0.191 g, 0.446 mmol, 78.1% yield). MS (apci) m/z=424.2 (M+H).

Provenance & Evidence