L-Alaninol → HCID 59910456, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 7-benzylsulfinyl-3-(2-chlorophenyl)-1-(piperidin-4-yl)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one (650 mg, 1.136 mmol) in 1,2-dimethoxyethane (0.5mL) was added (S)-(+)-2-amino-1-propanol (250 mg, 3.33 mmol). The reaction was warmed to 100° C. under argon for 2 hours. The reaction was placed directly on a flash silica column using 92:8-90:10 dichloromethane/methanol as eluant to give 300 mg of the (S)-3-(2-chlorophenyl)-7-(2-hydroxy-1-methylethylamino)-1-(piperidin-4-yl)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one, which was redissolved in 5 mL of dichloromethane and 5 mL trifluoroacetic acid. After 5 hours the solvents were removed in vacuo and 5 mL of ethyl acetate and 5 mL of 10% sodium bicarbonate were added. The organic layer was separated, washed with brine, dried over magnesium sulfate and concentrated in vacuo to give 130 mg of the title compound as a white foam that was dissolved in ethyl acetate and treated with 1 equivalent of hydrochloric acid in 1.0M ether. The precipitate was collected, washed with ether and dried in vacuo to give 115 mg of the hydrochloride salt of (S)-3-(2-chloro-phenyl)-7-(2-hydroxy-1-methylethylamino)-1-(piperidin-4-yl)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one.

Provenance & Evidence