Sodium Bicarbonate → HCID 58504538, compound

Participants

Reaction Conditions

Reaction Steps

Into a 25 mL sealable tube under nitrogen were combined 4-chloro-6-[(3R)-3-methyl-4-morpholinyl]-2-pyrimidinamine (500 mg, 2.19 mmol) and (4-cyano-3-fluorophenyl)boronic acid (0.397 g, 2.4 mmol) in 1,4-dioxane (10 mL). Saturated aqueous NaHCO3 (5 mL) was added, and the resulting mixture was degassed with nitrogen for 10 minutes. Pd(Ph3P)4 (0.126 g, 0.11 mmol) was added, the vessel was sealed, and the reaction mixture was stirred at 95° C. overnight. The reaction was cooled to room temperature, solids and other insoluble impurities formed during the reaction were filtered, and the orange filtrate was concentrated. The resulting solid was partitioned between EtOAc and water, and extracted with EtOAc (2×) and CH2Cl2 (2×). The organic layer was separated, washed with water and brine, dried (MgSO4), filtered and concentrated. The resulting solid was dissolved in CH2Cl2 and purified by flash chromatography on SiO2 (gradient: 100% CH2Cl2 to 15% of 90/10/1 CH2Cl2/CH3OH/NH4OH). Fractions were evaporated, and the solids were triturated with Et2O and filtered to afford the title compound (403 mg) as a yellow solid. LC-MS (ES) m/z=314 [M+H]+.

Provenance & Evidence