Water → HCID 178491936, compound

Participants

Reaction Steps

1-[trans-4-(tert-Butyl-dimethyl-silanyloxy)-cyclohexyl]-3-(4-methoxy-phenyl)-7-phenylamino-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one (from Example 3b supra) (139 mg, 0.25 mmol) was dissolved at 0° C. in a 50% solution of trifluoroacetic acid in dichloromethane (5 mL) that contained water (330 μL). After stirring for 1.5 hours the reaction mixture was partitioned between ethyl acetate and 1 N aqueous sodium hydroxide and the pH of the aqueous layer was adjusted to 12 by adding solid sodium hydroxide. The organic layer was then washed with water, dried over sodium sulfate, filtered and concentrated to the crude product. Purification by silica gel column chromatography with 0–100% ethyl acetate in hexanes gradient followed by a precipitation out of tetrahydrofuran with excess of pentane afforded 1-(trans-4-hydroxy-cyclohexyl)-3-(4-methoxy-phenyl)-7-phenylamino-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one as an off-white solid. (Yield 72 mg, 65%).

Provenance & Evidence