2,4,6-Trichloropyrimidine → HCID 59198368, compound

Participants

Reaction Steps

A solution of 2,4,6-trichloropyrimidine (2.0 mL, 17.4 mmol), 3-amino-6-methoxypyridine (1.5 mL, 19.1 mmol) and diisopropylethylamine (6.1 mL, 34.8 mmol) in acetonitrile (100 mL) was stirred at 55° C. under N2 for 15 hours. The reaction mixture was then partitioned between EtOAc (400 mL) and NaHCO3(sat.) (100 mL). The organic layer was separated, washed with brine (75 mL), dried over Na2SO4, concentrated, and purified by silica gel chromatography (20-30% EtOAc/hexanes) to yield 2,6-dichloro-N-(6-methoxypyridin-3-yl)pyrimidin-4-amine (2.51 g, 53%) as an off-white solid. LCMS (m/z): 270.9 and 272.9 (MH+); 1H NMR (CDCl3): δ 8.13 (d, J=2.7 Hz, 1H), 8.55 (dd, J=8.5, 2.7 Hz, 1H), 6.84 (d, J=8.4 Hz, 1H), 6.84(bs, 1H), 6.35 (s, 1H), 3.97 (s, 3H).

Provenance & Evidence