(4-Cyano-3-fluorophenyl)boronic acid → HCID 58504701, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-chloro-6-{(2R,5R)-2-[(dimethylamino)methyl]-5-methyl-4-morpholinyl}-N-methyl-2-pyrimidinamine (60 mg, 0.20 mmol), (4-cyano-3-fluorophenyl)boronic acid (73 mg, 0.44 mmol), and Pd(PPh3)4 (12 mg, 0.010 mmol) in 1,4-dioxane (2 mL) and saturated aqueous NaHCO3 (1 mL) was degassed with nitrogen for 10 minutes. The vial was then capped and stirred at 100° C. for 15 hours. The mixture was cooled, diluted with saturated aqueous NaHCO3 (5 mL) and water (5 mL), and extracted with EtOAc (2×10 mL). The extracts were washed with brine (10 mL), dried (Na2SO4), filtered, and concentrated in vacuo. The residue was purified by flash chromatography (10 g SiO2, CH2Cl2 to 95/5/0.5 CH2Cl2/CH3OH/NH4OH gradient) to give the title compound (58 mg, about 85% purity) as a yellow oil. LC-MS (ES) m/z=385 [M+H]+.

Provenance & Evidence