Methyl iodide → 3-(4-methoxy-phenyl)-1-methyl-7-phenylamino-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidine-2-one

Participants

Reaction Steps

To the suspension of 3-(4-methoxy-phenyl)-7-phenylamino-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one (34.7 mg, 0.1 mmol) (from Example 24a supra) in tetrahydrofuran (5 mL) was added sodium hydride (60%, 10 mg, 0.25 mmol) (Aldrich) followed by methyl iodide (0.032 mL, 0.5 mmol) (Aldrich) in one portion. The reaction mixture was stirred at room temperature overnight and then heated under reflux for 5 hours. The reaction was then quenched with saturated aqueous ammonium chloride solution and extracted with ethyl acetate (3×50 mL). The combined organic extracts were filtered to give 3-(4-methoxy-phenyl)-1-methyl-7-phenylamino-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidine-2-one as a white solid. (Yield 20.9 mg, 57.9%).

Provenance & Evidence