Dichloromethane → 6-(3,5-dimethoxyphenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidine

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-chloro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidine (5.2 mmol), (3,5-dimethoxyphenyl)boronic acid (1.0 g, 5.7 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complexed with dichloromethane (1:1) (0.3 g, 0.4 mmol) and potassium phosphate (2.2 g) in 1,4-dioxane (10 mL) and water (2 mL) in a reaction vial was degassed and sealed. The mixture was stirred at 100° C. for 3 h. After cooling, the reaction mixture was extracted with ethyl acetate (3×20 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-35%) to afford the desired product. LCMS (M+H)+=341.1.

Provenance & Evidence