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

Participants

Reaction Conditions

Reaction Steps

To a 5-mL microwave vial was added 4-chloro-N-methyl-6-[(3R)-3-methyl-4-morpholinyl]-2-pyrimidinamine (200 mg, 0.824 mmol), (4-cyano-3-fluorophenyl)boronic acid (177 mg, 1.071 mmol), PdCl2(dppf).CH2Cl2 adduct (33.6 mg, 0.041 mmol), K2CO3 (1.236 mL, 2.472 mmol), and 1,4-dioxane (3 mL). The reaction mixture was heated at 140° C. for 10 minutes in a microwave reactor. The 1,4-dioxane was removed, and the aqueous layer was extracted with EtOAc (2×20 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 (294 mg) as a yellow oil. LC-MS (ES) m/z=328 [M+H]+.

Provenance & Evidence