Triacetoxyperiodinane → (4,6-dichloropyrimidin-5-yl)[1-methyl-5-(4-methylphenyl)-1H-pyrazol-4-yl]methanone

Participants

Reaction Steps

To a mixture of (4,6-dichloropyrimidin-5-yl)[1-methyl-5-(4-methylphenyl)-1H-pyrazol-4-yl]methanol (C4) (60 g, 170 mmol) and chloroform (1.8 L) was added Dess-Martin periodinane (110 g, 258 mmol) in portions at room temperature. After the addition was complete, the reaction mixture was stirred at room temperature for 2 hours, and then concentrated in vacuo. The residue was taken up in ethyl acetate and washed with aqueous sodium hydroxide solution (0.5 N, 2×800 mL), then with saturated aqueous sodium chloride solution, dried over sodium sulfate, and concentrated under reduced pressure. Recrystallization from methanol afforded the product as a light yellow solid. Yield: 31.3 g, 90.1 mmol, 53%. LCMS m/z 346.9 (M+1). 1H NMR (400 MHz, CDCl3) δ 2.33 (s, 3H), 3.69 (s, 3H), 7.07-7.15 (br AB quartet, JAB=8 Hz, ΔνAB=8 Hz, 4H), 8.15 (s, 1H), 8.49 (s, 1H).

Provenance & Evidence