Sodium Bicarbonate → HCID 58504496, compound

Participants

Reaction Conditions

Reaction Steps

In a 25 mL sealable tube under nitrogen were combined 4-chloro-6-(hexahydro-1H-azepin-1-yl)-2-pyrimidinamine (600 mg, 2.65 mmol) and (4-cyano-3-fluorophenyl)boronic acid (0.437 g, 2.65 mmol) in 1,4-dioxane (10.6 mL). Saturated aqueous NaHCO3 (2.65 mL) was added, and the resulting mixture was degassed with nitrogen for 5 minutes. Pd(Ph3P)4 (0.153 g, 0.13 mmol) was added, the vessel was sealed, and the reaction mixture was stirred overnight at 95° C. The reaction was cooled to room temperature, and the organic layer was separated and concentrated. The resulting solid was partitioned between EtOAc and water. The organic layer was separated, dried (MgSO4), filtered and concentrated. Flash chromatography on SiO2 (eluent: 90/10/1 CHCl3/CH3OH/NH4OH) afforded the title compound (547 mg, 62%) as a yellow solid. LC-MS (ES) m/z=312 [M+H]+.

Provenance & Evidence