Potassium Carbonate → (2,4-Dichloro-pyrimidin-5-yl-methyl)-(4-ethyl-phenyl)-amine

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Reaction Steps

A heterogeneous mixture of 2,4-dichloro-5-(iodomethyl)pyrimidine (31.07 g, 107.3 mmol) (from Example 1c supra) and potassium carbonate (74 g, 536.5 mmol) in acetone (535 mL) was treated with 4-ethylaniline (13.3 mL, 107.3 mmol) (Aldrich). The mixture was stirred at room temperature overnight, then diluted with water (500 mL) and extracted with ethyl acetate. The combined organic layers were successively washed with 1 N aqueous hydrochloric acid, saturated aqueous sodium bicarbonate solution and brine, then dried over anhydrous sodium sulfate, filtered and concentrated under reduce pressure. The crude mixture was purified by flash chromatography (20% ethyl acetate in hexanes) to give (2,4-dichloro-pyrimidin-5-yl-methyl)-(4-ethyl-phenyl)-amine as a beige solid. (Yield 21.4 g, 70%).

Provenance & Evidence