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

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.

ORD record

ord-2251bfa1424046dd9f089bf5e752bd43

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07994317B2