Triacetoxyperiodinane → 1-(2-((3-Bromo-5-methylphenyl)amino)pyrimidin-4-yl)ethanone

Participants

Reaction Steps

1-(2-((3-Bromo-5-methylphenyl)amino)pyrimidin-4-yl)ethanol (3.27 g, 10.59 mmol) was dissolved in dichloromethane (14 mL). Dess-Martin Periodinane (9.0 g, 21.2 mmol) was added, and the resultant suspension was stirred vigorously for 14 h at room temperature. The mixture was diluted with saturated aqueous sodium bicarbonate and sodium thiosulfate. The heterogeneous mixture was extracted with dichloromethane (2×). The combined organic extracts were dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on silica (10-40% ethyl acetate/hexanes) to afford 1-(2-((3-bromo-5-methylphenyl)amino)pyrimidin-4-yl)ethanone as a yellow solid. MS ESI calc'd. for C13H13BrN3O [M+H]+ 306, 308. found 306, 308. 1H NMR (500 MHz, CDCl3) δ 8.64 (d, J=4.9 Hz, 1H), 7.93 (s, 1H), 7.35-7.30 (m, 2H), 7.05 (s, 1H), 2.71 (s, 3H), 2.35 (s, 3H).

Provenance & Evidence