Triacetoxyperiodinane → Triacetoxyperiodinane

Participants

Reaction Steps

To a solution of 1-(3-{4-amino-6-[methyl(phenyl)amino]-1,3,5-triazin-2-yl}-1,2,4-oxadiazol-5-yl)piperidin-4-ol (Intermediate 132, 120 mg, 0.325 mmol) in DCM (20 mL) at 0 C was added Dess-Martin Periodinane (138 mg, 0.325 mmol). The resulting reaction mixture was stirred at room temperature for 2 h and then further Dess-Martin Periodinane (138 mg, 0.325 mmol) was added. The reaction mixture was stirred for a further 16 h at room temperature and then quenched with a saturated sodium bicarbonate aq. solution (10 mL). The resulting bi-layer was separated and the organics washed further with a 1M aq. HCl solution (10 mL). Organics were dried over magnesium sulfate, evaporated to dryness and purified by silica chromatography (0 to 3% MeOH in DCM) to afford the title compound as an off-white solid (Dess-Martin Periodinane impurities (17%) also present) (179 mg, 150%). Method C HPLC-MS: MH+ requires m/z=367. Found: m/z=367, Rt=1.14 min (74%).

Provenance & Evidence