反应详情

To a solution of 5-Bromo-4-cyclopentyloxy-2-{1-[4-(4-methoxy-benzenesulfonyl)-piperazin-1-yl]-ethyl}-pyrimidine (30.0 g, 0.06 mmol) in ethanol (10 ml) was added 10 mg platinum on carbon (0.5% wt). The solution was degassing three times and the hydrogen gas was introduced through a hydrogen balloon. The reaction was heated to reflux for 18 hours at room temperature. The solution was filtrated through a celite column and the solvent was evaporated. Water (5 ml) was then added to the solution and the mixture was extracted with dichloromethane (10 ml). The organic layer was then washed with 10% sodium bisulfite solution, and then washed with saturated brine (2×30 ml). The combined organic phase was collected and dried over magnesium sulfate, filtered and concentrated under reduced pressure to yield a brown crude product. The resulting residue was purified by silica gel chromatography with 50% dichloromethane in hexane. The product was collected and was dried under reduced pressure to give the 4-Cyclopentyloxy-2-{1-[4-(4-methoxy-benzenesulfonyl)-piperazin-1-yl]-ethyl}-pyrimidine (Yield 15 mg, 60%. 1HNMR (400 MHz, CDCl3): δ 1.60-1.54 (m, 2H), 1.64 (d, J=6.82 Hz, 3H), 1.76-1.67 (m, 4H), 1.96-1.84 (m, 2H), 3.35-3.12 (m, 4H), 3.50-3.35 (m, 2H), 3.05 (s, 3H), 4.41 (q, 1H, J=13.64, 7.33 Hz), 5.38 (m, 1H), 6.60 (d, J=5.81, 1H), 6.94 (d, J=8.84, 2H), 7.56 (d, J=8.84, 2H), 8.32 (d, J=5.81, 1H). MS m/z calc. 446.2 found (ESI); 447.2 (M+1)+. Retention time 2.76 minutes.

1. customThe solution was degassing three times
2. additionthe hydrogen gas was introduced through a hydrogen balloon
3. temperatureThe reaction was heated
4. filtrationThe solution was filtrated through a celite column
5. customthe solvent was evaporated
6. additionWater (5 ml) was then added to the solution
7. extractionthe mixture was extracted with dichloromethane (10 ml)
8. washThe organic layer was then washed with 10% sodium bisulfite solution
9. washwashed with saturated brine (2×30 ml)
10. customThe combined organic phase was collected
11. dry with materialdried over magnesium sulfate
12. filtrationfiltered
13. concentrationconcentrated under reduced pressure
14. customto yield a brown crude product
15. customThe resulting residue was purified by silica gel chromatography with 50% dichloromethane in hexane
16. customThe product was collected
17. customwas dried under reduced pressure