Sodium Bicarbonate → HCID 58504760, compound

Participants

Reaction Conditions

Reaction Steps

In a 25 mL sealable tube under nitrogen were combined 6-chloro-N4-cyclohexyl-2,4-pyrimidinediamine (0.75 g, 3.31 mmol) and (4-cyano-3-fluorophenyl)boronic acid (0.546 g, 3.31 mmol) followed by 1,4-dioxane (13.2 mL) and saturated aqueous NaHCO3 (3.3 mL). The resulting mixture was degassed with nitrogen for 5 minutes. Pd(Ph3P)4 (0.19 g, 0.165 mmol) was added, the vial was sealed, and the reaction mixture was stirred for 16 hours at 95° C. The reaction was cooled to room temperature, decanted, and concentrated. The resulting orange oil was partitioned between EtOAc and water. The organic layer was separated, washed with brine, dried (MgSO4), filtered and concentrated. To the resulting yellow solid was added CH3CN (5 mL), and the mixture was sonicated. Filtration of the solid and washing with minimal CH3CN afforded the title compound (387 mg, 36%) as a light tan solid. LC-MS (ES) m/z=312 [M+H]+.

Provenance & Evidence