3-Fluoroaniline → HCID 67390628, compound

Participants

Reaction Steps

To a solution of 4-(2-chloro-4-pyridinyl)-N-(tetrahydro-2H-pyran-4-yl)-2-pyrimidinamine (i.e., the product of Step A) (500 mg, 1.7 mmol) in toluene (15 mL) was added 3-fluoroaniline (400 uL, 4.1 mmol), palladium(II) acetate (50 mg, 0.20 mmol), (±)-BINAP (100 mg, 0.16 mmol) and cesium carbonate (1.9 g, 5.8 mmol), and the resulting mixture was stirred at reflux for 4.5 h. The cooled mixture was partitioned between ethyl acetate and water, and the organic layer was washed with brine, dried over MgSO4 and filtered. The solvent was removed under reduced pressure to give a residue that was chromatographed on silica gel eluted with 15% to 85% ethyl acetate in hexanes to afford 330 mg of title compound as a solid, m.p. 190-192° C.

Provenance & Evidence