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

HRID 238244Notes

Reaction equation

HRID 238244 reaction equation
[Br:1][C:2]1[C:3](=[O:27])[NH:4][C:5]([CH:8]([N:10]2[CH2:15][CH2:14][N:13]([S:16]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)(=[O:18])=[O:17])[CH2:12][CH2:11]2)[CH3:9])=[N:6][CH:7]=1.I[CH:29]1[CH2:33][CH2:32][CH2:31][CH2:30]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[C:3]([O:27][CH:29]2[CH2:33][CH2:32][CH2:31][CH2:30]2)=[N:4][C:5]([CH:8]([N:10]2[CH2:15][CH2:14][N:13]([S:16]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)(=[O:18])=[O:17])[CH2:12][CH2:11]2)[CH3:9])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 73784IodocyclopentaneHCID 599931295-Bromo-2-{1-[4-(4-methoxy-benzenesulfonyl)-piperazin-1-yl]-ethyl}-3H-pyrimidin-4-one

Product 1

HCID 599932605-Bromo-4-cyclopentyloxy-2-{1-[4-(4-methoxy-benzenesulfonyl)-piperazin-1-yl]-ethyl}-pyrimidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

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.

Workup

  1. temperatureAfter cooling down to room temperature
  2. filtrationthe K2CO3 was filtrated
  3. customPurification
  4. customThe product was collected
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-303e47e551034542af74ad97d46c0722
Source dataset
uspto-grants-2014_02
Patent number
US08642609B2

Reaction notes

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