Potassium Carbonate → 5-Bromo-2-{1-[4-(4-methoxy-benzenesulfonyl)-piperazin-1-yl]-ethyl}-3H-pyrimidin-4-one

HRID 238243Notes

Reaction equation

HRID 238243 reaction equation
[Br:1][C:2]1[C:3](=[O:11])[NH:4][C:5]([CH:8](Br)[CH3:9])=[N:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+].[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([S:26]([N:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)(=[O:28])=[O:27])=[CH:22][CH:21]=1>C(#N)C>[Br:1][C:2]1[C:3](=[O:11])[NH:4][C:5]([CH:8]([N:32]2[CH2:31][CH2:30][N:29]([S:26]([C:23]3[CH:22]=[CH:21][C:20]([O:19][CH3:18])=[CH:25][CH:24]=3)(=[O:28])=[O:27])[CH2:34][CH2:33]2)[CH3:9])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 7975601-((4-Methoxyphenyl)sulfonyl)piperazineHCID 599933765-bromo-2-(1-bromo-ethyl)-3H-pyrimidin-4-one

Product 1

HCID 599931295-Bromo-2-{1-[4-(4-methoxy-benzenesulfonyl)-piperazin-1-yl]-ethyl}-3H-pyrimidin-4-oneYield 53.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In a round bottom flask containing 5-bromo-2-(1-bromo-ethyl)-3H-pyrimidin-4-one (1.0 g, 3.5 mmol) in acetonitrile (30 ml) was added KI (0.9 g, 5.3 mmol), K2CO3 (1.2 g, 5.3 mmol), and (1-(4-Methoxy-benzenesulfonyl)-piperazine (983 mg, 3.5 mmol). The reaction was heated at reflux for 12 hours. The solution was concentrated under reduced pressure. The residue was partitioned between water (10 ml) and dichloromethane (15 ml). The organic layer was dried over magnesium sulfate, filtered and concentrated under reduced pressure. The solvent was removed under vacuum. The resulting residue purified by column chromatography (ethyl acetate: hexanes 1:1) to give 5-bromo-2-{1-[4-(4-methoxy-benzenesulfonyl)-piperazin-1-yl]-ethyl}-3H-pyrimidin-4-one (Yield 854 mg, 53%). 1H NMR (400 MHz, CDCl3): δ 1.28 (d, J=7.0 Hz, 3H), 2.62-2.49 (m, 4H), 3.00-2.94 (m, 4H), 3.84 (s, 3H), 4.05 (q, 1H, J=7.0 Hz), 6.97 (d, J=11.8 Hz, 2H), 7.62 (d, J=11.8 Hz, 2H), 8.11 (s, 1H). MS m/z calc. 457.3, found (ESI); 457.2 (M+1)+. Retention time 2.50 minutes.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 12 hours
  3. concentrationThe solution was concentrated under reduced pressure
  4. customThe residue was partitioned between water (10 ml) and dichloromethane (15 ml)
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe solvent was removed under vacuum
  9. customThe resulting residue purified by column chromatography (ethyl acetate: hexanes 1:1)

Sources & evidence

ORD record
ord-b70e1bcfca4c44eaa9412537f2b082da
Source dataset
uspto-grants-2014_02
Patent number
US08642609B2

Reaction notes

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