Methyl iodide → 4,6-Dichloro-n-methylpyrimidin-2-amine

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Reaction Steps

To a mixture of N-(4,6-dichloro-pyrimidin-2-yl)-2,2,2-trifluoro-acetamide (4.6 g, 17.7 mmol) and potassium carbonate (4.9 g, 35.4 mmol) in acetone (100 ml) was added iodomethane (1.3 ml, 21.2 mmol). After stirring for 12 hours, the mixture was filtered through a pad of celite under suction. The filtrate was concentrated under reduced pressure and the residue was treated with methanol (150 ml) tetrahydrofuran (30 ml), and a solution of potassium carbonate (5.0 g, 51 mmol) in water (15 ml). After stirring for 1 hour, the mixture was concentrated under reduced pressure. The residue was partitioned between ethyl acetate (150 ml) and saturated aqueous sodium chloride solution (100 ml). The organic phase was dried over magnesium sulfate. After evaporation of the solvent under reduced pressure, the residue was purified by flash chromatography eluting with ethyl acetate-hexane (1:6 followed by 1:4) to give N-(4,6-dichloro-pyrimidin-2-yl)-methyl-amine (2.7 g, 85% yield). 1H NMR (CDCl3) δ 3.04 (d, 3H, J=5.1 Hz, CH3), 5.50 (br s, 1H, NH), 6.63 (s, 1H, Ar).

Provenance & Evidence