(+-)-2-Butanol → HCID 86610591, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension (1 ml) of copper bromide (227 mg) in tetrahydrofuran is added dropwise 65% solution (982 mg) of bis(2-methoxyethoxy)aluminum sodium hydride in toluene under ice-cooling, and the mixture is stirred at the same temperature for 30 minutes. The reaction solution is cooled to −78°C., and thereto is added 2-butanol (0.29 ml). Subsequently, a solution (0.5 ml) of (2R*,4S*)-4-{[3,5-bis(trifluoromethyl)benzyl]-[5-(2-cyanovinyl)pyrimidin-2-yl]}amino-2-ethyl-6-methoxy-3,4-dihydro-2H-[1,5]naphthyridine-1-carboxylic acid ethyl ester (100 mg) in tetrahydrofuran is added thereto dropwise, and the mixture is stirred at the same temperature for 2 hours. After allowing to warm to room temperature, the mixture is stirred for additional 2 hours. To the reaction solution is added a saturated aqueous ammonium chloride solution, and the mixture is partitioned by adding ethyl acetate. The organic layer is washed with a saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue is purified by tin layer silica gel chromatography (hexane: ethyl acetate=2:1) to give (2R*,4S*)-4-{[3,5-bis(trifluoromethyl)benzyl]-[5-(2-cyanoethyl)pyrimidin-2-yl]}amino-2-ethyl-6-methoxy-3,4-dihydro-2H-[1,5]naphthyridine-1-carboxylic acid ethyl ester (74 mg). MS (m/z): 637 [M+H]+

Provenance & Evidence