Triacetoxyperiodinane → [4-(azetidin-1-yl)-6-chloropyrimidin-5-yl]{1-methyl-5-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazol-4-yl}methanone

Participants

Reaction Conditions

Reaction Steps

A solution of [4-(azetidin-1-yl)-6-chloropyrimidin-5-yl]{1-methyl-5-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazol-4-yl}methanol (C15) (30 mg, 0.071 mmol) in dichloromethane (3 mL) was cooled to 0° C. and Dess-Martin periodinane (33.1 mg, 0.078 mmol) was added portion-wise. After completion of the addition, the reaction mixture was stirred for 1 hour at 0° C., then warmed to room temperature and stirred for an additional 18 hours. The reaction mixture was diluted with dichloromethane, and then quenched with aqueous sodium bicarbonate solution (1 mL) and aqueous sodium thiosulfate solution (1 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure. Chromatographic purification using silica gel [Gradient: 0% to 100% (95:2.5:2.5 ethyl acetate/methanol/triethylamine) in heptane] afforded the product. Yield: 29 mg, 0.069 mmol, 97%. LCMS m/z 423.1, 425.2 (M+1). 1H NMR (400 MHz, CD3OD) δ 2.30-2.39 (m, 2H), 3.78 (s, 3H), 3.99-4.07 (m, 4H), 7.89 (d, J=8.2 Hz, 1H), 8.00-8.13 (m, 3H), 8.72 (br s, 1H).

Provenance & Evidence