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

HRID 238243
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HRID 238243 반응식
[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
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참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-b70e1bcfca4c44eaa9412537f2b082da
출처 데이터셋
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08642609B2

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