Dichloromethane → 2,6-Difluoro-4-{2-(methylamino)-6-[(3R)-3-methyl-4-morpholinyl]-4-pyrimidinyl}benzonitrile

Participants

Reaction Conditions

Reaction Steps

To a 20-mL microwave vial was added 4-chloro-N-methyl-6-[(3R)-3-methyl-4-morpholinyl]-2-pyrimidinamine (500 mg, 2.060 mmol), (4-cyano-3,5-difluorophenyl)boronic acid (754 mg, 4.12 mmol), PdCl2(dppf).CH2Cl2 adduct (84 mg, 0.103 mmol), K2CO3 (2 M, 3.09 mL, 6.18 mmol), and 1,4-dioxane (9 mL). The reaction mixture was heated at 140° C. for 10 mins in a microwave reactor. The 1,4-dioxane was removed, and the aqueous layer was extracted with EtOAc (2×10 mL). The combined organics were dried over Na2SO4 and concentrated. The resulting residue was purified by flash chromatography (0-50% EtOAc in hexanes, 12 g column) to afford the title compound (312 mg) as a yellow solid. LC-MS (ES) m/z=346 [M+H]+.

Provenance & Evidence