5-Bromo-4-cyclopentyloxy-2-{1-[4-(4-methoxy-benzenesulfonyl)-piperazin-1-yl]-ethyl}-pyrimidine → 4-Cyclopentyloxy-2-{1-[4-(4-methoxy-benzenesulfonyl)-piperazin-1-yl]-ethyl}-pyrimidine

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Reaction Steps

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.

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