Sodium Iodide → 1-methyl-5-(3-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)pyridin-2(1H)-one

Participants

Reaction Conditions

Reaction Steps

Iodomethane (0.063 mL, 1.007 mmol) and sodium iodide (151 mg, 1.007 mmol) were added to a solution of N-[3-(6-methoxypyridin-3-yl)phenyl]-4-(trifluoromethyl)pyrimidin-2-amine (109 mg, 0.315 mmol) in MeCN (3.1 mL) at room temperature under nitrogen. The mixture was heated to 45° C. for 72 hours, then cooled to room temperature and concentrated in vacuo. The residue was diluted with water and extracted with ethyl acetate (2×). The combined organic layers were washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate/hexanes) to afford 1-methyl-5-(3-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)pyridin-2(1H)-one as an off-white solid. MS APC calc'd for C17H14F3N4O [M+H]+ 347. found 347. Check LCMS data. 1H NMR (400 MHz, Acetone-d6): δ 9.31 (s, 1H); 8.83 (d, J=4.9 Hz, 1H); 8.72 (s, 1H); 7.96 (d, J=8.2 Hz, 1H); 7.84 (d, J=7.8 Hz, 1H); 7.79 (t, J=7.8 Hz, 1H); 7.54 (d, J=7.4 Hz, 1H); 7.48 (t, J=7.9 Hz, 1H); 7.24 (d, J=4.9 Hz, 1H); 6.76 (d, J=8.2 Hz, 1H); 4.04 (s, 3H). APCI: [M+H]+ m/z 347.1.

Provenance & Evidence