Triacetoxyperiodinane → 2-[3-(4-Methoxy-phenyl)-2-oxo-propylamino]-3-methyl-5-naphthalen-2-yl-6-pyridin-4-yl-3H-pyrimidin-4-one

Participants

Reaction Steps

To a stirring solution of 2-[2-hydroxy-3-(4-methoxy-phenyl)-propylamino]-3-methyl-5-naphthalen-2-yl-6-pyridin-4-yl-3H-pyrimidin-4-one (765 mg, 1.55 mmol) in 20 mL dichloromethane was added Dess-Martin Periodinane (660 mg, 1.55 mmol). The dark red solution was stirred for 18 h at room temperature. The reaction mixture was diluted with 80 mL dichloromethane and washed twice with 15 mL 5% sodium bicarbonate, and dried over magnesium sulfate. The product was purified on 40 g silica eluting with 0 to 4% methanol/dichloromethane to provide the product as a yellow foam. The product was further purified on reverse phase high performance chromatography using an water/acetonitrile (0.1% TFA) gradient. The final sample was lyophilized from 50% acetonitrile/water to give a yellow powder. M+1=491.2.

Provenance & Evidence