Methylamine → 4,6-Dichloro-n-methylpyrimidin-2-amine

Participants

Reaction Steps

To a 0° C. mixture 2,4,6-trichloropyrimidine (0.50 g, 2.7 mmol) in THF (3 mL) was added methyl amine (2M THF, 3.0 mL, 6.0 mmol) dropwise. The reaction mixture was warmed to room temperature and stirred for 30 minutes, at which time LCMS indicated the formation of the desired product. The reaction mixture was treated with water (10 mL) and extracted with EtOAc (2×10 mL). The organics were washed with brine (10 mL), dried (Na2SO4), and evacuated. The crude material was purified by column chromatography (Gradient from 0-30% EtOAc in Hexanes) to afford 180 mg (1.01 mmol, 38%) of 2,6-dichloro-N-methyl-4-pyrimidinamine and 150 mg (0.85 mmol 31%) of 4,6-dichloro-N-methyl-2-pyrimidinamine. MS (ES+) m/e 178 [M+H]+ for each.

Provenance & Evidence