Hydrogen Peroxide → (+/-)-3-[7-[3-(2-dimethylamino-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-Dimethylamino-ethyl)-phenylamino]-3-(4-methoxy-phenyl)-4-methyl-2-oxo-3,4-dihydro-2H-pyrimido[4,5-d]pyrimidin-1-yl]-benzonitrile (92.7 mg; 0.17 mmol) (from Example 6 supra) was dissolved in dimethyl sulfoxide (1.0 mL) and the resulting solution was cooled in an ice-water bath. Aqueous sodium hydroxide (1 M; 300 μL; 0.30 mmol) was added, resulting in the precipitation of the benzonitrile. Aqueous hydrogen peroxide (30%; 53 μL; 0.52 mmol) was then added. The benzonitrile went back into solution and the product then precipitate out of solution. After 4 hours, the reaction was diluted with water. The solid was collected, washed with water and dried. Recrystallization from dichloromethane-ether gave (±)-3-[7-[3-(2-dimethylamino-ethyl)-phenylamino]-3-(4-methoxy-phenyl)-4-methyl-2-oxo-3,4-dihydro-2H-pyrimido[4,5-d]pyrimidin-1-yl]-benzamide. (Yield 72.9 mg; 76.1%). Melting Point: 215–230° C. HR-MS(ES+) m/z Calculated for C31H33N7O3 ([M+H]+): 552.2718; Found: 552.2722.

Provenance & Evidence