Sodium Carbonate → HCID 69203296, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (S)-3-iodo-1-[1-(2-methoxyethyl)-3-piperidyl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine acetate (0.64 g, 0.0014 mol), N-(5,7-dimethyl-1,3-benzoxazol-2-yl)-N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]amine (0.64 g, 0.00175 mol, 1.2 eq.), tetrakis(triphenylphosphine)palladium (0.081 g, 0.00007 mol) and sodium carbonate (0.37 g, 0.0035 mol) in N,N-dimethylformamide (15 mL) and water (7 mL) was heated at 80° C. for 16 hours under an atmosphere of nitrogen. The mixture was allowed to cool to ambient temperature, and the solvent was removed under the reduced pressure. The residue was partitioned between water (25 mL) and dichloromethane (50 mL). The aqueous layer was extracted with dichloromethane (3×50 mL). The combined organic extracts were washed with brine and dried over magnesium sulfate. The solvents were evaporated under the reduced pressure to leave a brownish oil, which was purified by flash column chromatography on silica using 2%-10% methanol/dichloromethane as a mobile phase to give (S)-N2-(4-{4-amino-1-[1-(2-methoxyethyl)-3-piperidyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}phenyl)-5,7-dimethyl-1,3-benzoxazol-2-amine (0.60 g, 0.0012 mol).

Provenance & Evidence