反应详情

Triphenylphosphine (1.5 g, 5.7 mmol) is added to a solution of N-methoxy-3-bromopyrrolidin-2-one (Ikuta, et al. J. Med. Chem. 1984, 30, 1995) (1.0 g, 5.2 mmol) in THF (10 mL) and the mixture is warmed to reflux under an argon atmosphere for 12 hours. The reaction mixture is cooled in an ice bath and the solvent is decanted away from the resulting solid. The solid is added to a solution of triethylamine (0.93 g, 9.3 mmol) and 4,6-bis-(1,1-dimethylethyl)-5-hydroxypyrimidine-2-carboxaldehyde (0.97 g, 4.1 mmol) in ethanol (10 mL). The resulting mixture is warmed to reflux for 3 hours under an argon atmosphere. The mixture is cooled to room temperature, the EtOH is evaporated and the residue is partitioned between 50 mL EtOAc and 50 mL H2O. The organic extract is dried over MgSO4. The solvent is evaporated and the solid is recrystallized from Et2O/hexane. Yield of 3-[[4,6-bis-(1,1-dimethylethyl)-5-hydroxy-2-pyrimidinyl]methylene]-N-methoxypyrrolidin-2-one=0.34 g (20%), mp 184°-186° C.

1. temperaturethe mixture is warmed
2. temperatureto reflux under an argon atmosphere for 12 hours
3. temperatureThe reaction mixture is cooled in an ice bath
4. customthe solvent is decanted away from the resulting solid
5. temperatureThe resulting mixture is warmed
6. temperatureto reflux for 3 hours under an argon atmosphere
7. customthe EtOH is evaporated
8. customthe residue is partitioned between 50 mL EtOAc and 50 mL H2O
9. extractionThe organic extract
10. dry with materialis dried over MgSO4
11. customThe solvent is evaporated
12. customthe solid is recrystallized from Et2O/hexane