反应详情

(−)-(1S,3S)-1-[3-(tert-Butyl-dimethyl-silanyloxy)-cyclopentyl]-3-(4-methoxy-phenyl)-7-phenylamino-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one (445 mg, 0.82 mmol) (from Example 29g supra) was dissolved in a 25% trifluoroacetic acid in dichloromethane solution (5 mL) and water (300 μL) at 0° C. After stirring for 30 minutes the mixture was partitioned between ethyl acetate and 1 N aqueous sodium hydroxide and the pH of the aqueous layer was adjusted to 12 via the addition of solid sodium hydroxide. The organic layer was collected, dried over sodium sulfate, filtered and concentrated to a residue that was purified by chromatography with a silica gel column and a 0–100 ethyl acetate in hexanes to 0–40% tetrahydrofuran in ethyl acetate gradient to give (−)-(1S,3S)-1-(3-hydroxy-cyclopentyl)-3-(4-methoxy-phenyl)-7-phenylamino-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one as a white solid. (Yield 307 mg, 86%).

1. customwas partitioned between ethyl acetate and 1 N aqueous sodium hydroxide
2. additionthe pH of the aqueous layer was adjusted to 12 via the addition of solid sodium hydroxide
3. customThe organic layer was collected
4. dry with materialdried over sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated to a residue that
7. customwas purified by chromatography with a silica gel column