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

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-Bromo-2-{1-[4-(4-methoxy-benzenesulfonyl)-piperazin-1-yl]-ethyl}-3H-pyrimidin-4-one(100 mg, 0.22 mmol) in 2 ml DMF was added iodo-cyclopentane (85.7 mg, 0.22 mmol) and potassium carbonate (152.0 mg, 1.1 mmol). This reaction was heated to 90° C. for 18 hours. After cooling down to room temperature, the K2CO3 was filtrated. Purification was accomplished by HPLC (Gilson-215, 0.035% TFA in acetonitrile and 0.05% water as mobile phase). The product was collected and dried under reduced pressure to give 5-bromo-4-cyclopentyloxy-2-{1-[4-(4-methoxy-benzenesulfonyl)-piperazin-1-yl]-ethyl}-pyrimidine. (Yield 11.5 mg, 9.9%). 1H NMR (400 MHz, CDCl3): δ 1.30 (d, J=6.82 Hz, 3H), 1.64-1.51 (m, 2H), 1.82-1.67 (m, 4H), 1.96-1.82 (m, 2H), 2.65-2.52 (m, 4H), 3.00-2.85 (m, 4H), 3.67 (q, J=6.82 Hz, 1H), 3.78 (s, 3H), 5.41 (m, 1H), 6.90 (d, J=9.09, 2H), 7.59 (d, J=9.09, 2H), 8.39 (s, 1H). MS m/z calc. 525.2 found (ESI); 526.2 (M+1)+. Retention time 2.91 minutes.

Provenance & Evidence