Triacetoxyperiodinane → 2-[3-Phenyl-2-oxo-propylamino]-3-methyl-5-naphthalen-2-yl-6-pyridin-4-yl-3H-pyrimidin-4-one

Participants

Reaction Steps

To a striring suspension of 2-(2-hydroxy-3-phenyl-propylamino)-3-methyl-5-naphthalen-2-yl-6-pyridin-4-yl-3H-pyrimidin-4-one (150 mg, 0.32 mmol) in 5 mL dry acetonitrile and 5 mL dichloromethane was added Dess-Martin Periodinane (206 mg, 0.49 mmol). The reaction mixture turned to an orange color within 3 min. After 30 min, TLC (95:5 dichloromethane/methanol) showed approximately 15% of the starting material remained. More Dess-Martin Periodinane (50 mg, 0.12 mmol) was added and the reaction was stirred for and additional 30 min. The curde product was purified on 10 g silica eluting with 0 to 3% methanol/dichloromethane to give a clear film. The material was further purified on reverse phase high performance chromatography eluting with water/acetonitrile (0.1% TFA) gradient. The final material was lyophilized from 50% acetonitrile/water to give a pale yellow powder. M+1=461.3. NMR (CD3CN/D2O 3:1) s (3H; 3.5 ppm), s (2H; 3.8 ppm), s (2H; 4.3 ppm), dd (2H; 7.15 ppm), m (4H, 7.2-7.3 ppm), m (3H, 7.45-7.55 ppm), d (2H, 7.62 ppm), d (1H, 7.72 ppm), d (1H, 7.84 ppm), d (1H, 7.88 ppm), d (2H, 8.39 ppm). M+1=461.2.

Provenance & Evidence