Hydrogen Peroxide → (+/-)-3-[7-[3-(2-diethylamino-ethyl)-phenylamino]-3-(4-methoxy-phenyl)-4-methyl-2-oxo-3,4-dihydro-2H-pyrimido[4,5-d]pyrimidin-1-yl]-benzamide

Participants

Reaction Steps

(±)-3-[7-[3-(2-Diethylamino-ethyl)-phenylamino]-3-(4-methoxy-phenyl)-4-methyl-2-oxo-3,4-dihydro-2H-pyrimido[4,5-d]pyrimidin-1-yl]-benzonitrile (0.35 g; 0.60 mmol) (from Example 5b supra) was dissolved in dimethyl sulfoxide (3.5 mL) and the resulting solution was cooled in an ice-water bath. Aqueous sodium hydroxide (1 M; 1.15 mL; 1.15 mmol) was added, resulting in the precipitation of the benzonitrile. Aqueous hydrogen peroxide (30%; 195 μL; 1.91 mmol) was then added. The benzonitrile slowly went back into solution. After 3 hours, water was added to the reaction mixture. The product initially separated out as a gum which then solidified. The solid was collected, washed with water and dried. Recrystallization from dichloromethane-ether gave (±)-3-[7-[3-(2-diethylamino-ethyl)-phenylamino]-3-(4-methoxy-phenyl)-4-methyl-2-oxo-3,4-dihydro-2H-pyrimido[4,5-d]pyrimidin-1-yl]-benzamide. (Yield 0.30 g; 84.8%).

Provenance & Evidence