反应详情

5-Benzyloxy-2-(2-bromobenzyl)-6-oxo-3,6-dihydro-pyrimidine-4-carboxylic acid [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-isopropylamide (69) (0.75 g, 1.22 mmol, Eq: 1.00) was dissolved in tetrahydrofuran (10 ml). HCl (915 μl, 1.83 mmol, Eq: 1.5) was added and the resulting mixture was stirred at room temperature. After 30 minutes the solvent was mostly removed. The residue was partitioned between ethyl acetate and 1M NaOH. The aqueous layer was washed with ethyl acetate, the organic layers were washed with brine, combined, dried over Na2SO4, filtered and concentrated. The remaining brown oil was triturated in ethyl acetate/ether. The solid was collected by filtration, washed with a little ethyl acetate and dried to afford 5-benzyloxy-2-(2-bromobenzyl)-6-oxo-3,6-dihydro-pyrimidine-4-carboxylic acid (2-hydroxyethyl)-isopropylamide (70) (0.21 g, 420 μmol, 34.4% yield) as an off-white solid. The mother liquor also showed clean product (0.43 g, 68% yield) of brown solid.

1. customAfter 30 minutes the solvent was mostly removed
2. customThe residue was partitioned between ethyl acetate and 1M NaOH
3. washThe aqueous layer was washed with ethyl acetate
4. washthe organic layers were washed with brine
5. dry with materialdried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated
8. customThe remaining brown oil was triturated in ethyl acetate/ether
9. filtrationThe solid was collected by filtration
10. washwashed with a little ethyl acetate
11. customdried