3-Fluoroaniline → 4-[2-[(3-fluorophenyl)amino]-4-pyridinyl]-N-[1-methyl-2-(methylthio)ethyl]-2-pyrimidinamine

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-(2-chloro-4-pyridinyl)-N-[1-methyl-2-(methylthio)ethyl]-2-pyrimidinamine (i.e., the product of Step C) (150 mg, 0.5 mmol) in toluene (6.0 mL) was added 3-fluoroaniline (108 μL, 1.1 mmol), palladium(II) acetate (24 mg, 0.12 mmol), (±)-2,2′-bis(diphenylphosphino)-1,1′-binaphthalene ((±)-BINAP) (40 mg, 0.06 mmol) and cesium carbonate (700 mg, 2.2 mmol); the resulting mixture was stirred at 110° C. for 13 h. The mixture was allowed to cool and silica gel (300 mg) was added. The excess solvent was removed under reduced pressure, and the resulting solid was chromatographed on silica gel eluted with 5% to 60% ethyl acetate in hexanes to give 60 mg of the title compound as a yellow solid, m.p. 104-107° C.

Provenance & Evidence