2-Chloro-6-methylaniline → 4-[2-[(2-chloro-6-methylphenyl)amino]-4-pyridinyl]-N-(2-methoxy-1-methylethyl)-2-pyrimidinamine

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Reaction Steps

To a solution of 4-(2-chloro-4-pyridinyl)-N-(2-methoxy-1-methylethyl)-2-pyrimidinamine (i.e., the product of Step B) (100 mg, 0.35 mmol) in toluene (10 mL) was added 2-chloro-6-methylaniline (102 mg, 0.72 mmol), cesium carbonate (350 mg, 1.07 mmol), palladium(II) acetate (4 mg, 0.017 mmol) and ((±)-BINAP) (22 mg, 0.035 mmol), and the resulting mixture was stirred at reflux for 30 h. After cooling to room temperature, the mixture was concentrated, and purified using column chromatography on silica gel eluted with 40% ethyl acetate in hexanes to give 30 mg of the title compound as a solid.

Provenance & Evidence