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Potassium Carbonate → 9-(4-Chlorobutyl)-2-{[(1S)-1-methylbutyl]oxy}-8-(methyloxy)-9H-purin-6-amine

HRID 2036357
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HRID 2036357 반응식
[CH3:1][C@H:2]([O:6][C:7]1[NH:8][C:9]([NH2:18])=[C:10]2[C:14]([N:15]=1)=[N:13][C:12]([O:16][CH3:17])=[N:11]2)[CH2:3][CH2:4][CH3:5].C(=O)([O-])[O-].[K+].[K+].Br[CH2:26][CH2:27][CH2:28][CH2:29][Cl:30]>CN(C=O)C>[Cl:30][CH2:29][CH2:28][CH2:27][CH2:26][N:13]1[C:12]([O:16][CH3:17])=[N:11][C:10]2[C:14]1=[N:15][C:7]([O:6][C@@H:2]([CH3:1])[CH2:3][CH2:4][CH3:5])=[N:8][C:9]=2[NH2:18]
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참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 813641-Bromo-4-chlorobutaneHCID 178448283HCID 178448283, 화합물

생성물 1

HCID 582909339-(4-Chlorobutyl)-2-{[(1S)-1-methylbutyl]oxy}-8-(methyloxy)-9H-purin-6-amine수율 71.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
50 °C

실험 절차

2-{[(1S)-1-methylbutyl]oxy}-8-(methyloxy)-1H-purin-6-amine (1 g, 2.74 mmol) and potassium carbonate (0.946 g, 6.84 mmol) in DMF (12.5 ml) were stirred under nitrogen and heated to 50° C. for 1 hour. The mixture was then allowed to cool to ambient temperature and 1-bromo-4-chlorobutane (0.315 ml, 2.74 mmol) was added and stirring was continued under nitrogen at ambient temperature overnight. The mixture was then partitioned between ethyl acetate and water. The aqueous layer was washed with ethyl acetate and the combined organic extracts were washed with saturated brine and passed through a hydrophobic frit and evaporated in vacuo. The residue (1.0322 g) was dissolved in dichloromethane and loaded onto an amino cartridge (70 g) and eluted using a 0-100% ethyl acetate in cyclohexane gradient over 40 minutes. Product fractions were combined and evaporated to give the title compound as an off-white solid (667 mg).

후처리

  1. temperatureto cool to ambient temperature
  2. customThe mixture was then partitioned between ethyl acetate and water
  3. washThe aqueous layer was washed with ethyl acetate
  4. washthe combined organic extracts were washed with saturated brine
  5. customevaporated in vacuo
  6. dissolutionThe residue (1.0322 g) was dissolved in dichloromethane
  7. washeluted
  8. customover 40 minutes
  9. customevaporated

출처 및 근거

ORD 기록
ord-038372330ded4009be6cd474d7dadba2
출처 데이터셋
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08575181B2

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