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Potassium Carbonate → 2-(2-ethoxyethoxy)-8-methoxy-9-(tetrahydro-2H-pyran-4-ylmethyl)-9H-purin-6-amine

HRID 1011002
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HRID 1011002 반응식
FC(F)(F)C(O)=O.[CH2:8]([O:10][CH2:11][CH2:12][O:13][C:14]1[N:22]=[C:21]2[C:17]([N:18]=[C:19]([O:23][CH3:24])[NH:20]2)=[C:16]([NH2:25])[N:15]=1)[CH3:9].C(=O)([O-])[O-].[K+].[K+].CS(O[CH2:37][CH:38]1[CH2:43][CH2:42][O:41][CH2:40][CH2:39]1)(=O)=O>CN(C)C=O.C(OCC)(=O)C>[CH2:8]([O:10][CH2:11][CH2:12][O:13][C:14]1[N:22]=[C:21]2[C:17]([N:18]=[C:19]([O:23][CH3:24])[N:20]2[CH2:37][CH:38]2[CH2:43][CH2:42][O:41][CH2:40][CH2:39]2)=[C:16]([NH2:25])[N:15]=1)[CH3:9]
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참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 15166436Oxan-4-ylmethyl methanesulfonateHCID 1784679962-[2-(Ethyloxy)ethyl]oxy-8-(methoxy)-9h-purin-6-amine trifluoroacetic acid salt

생성물 1

HCID 576995812-(2-ethoxyethoxy)-8-methoxy-9-(tetrahydro-2H-pyran-4-ylmethyl)-9H-purin-6-amine수율 50.2%

시약·촉매·용매 2

HCID 6228Dimethylformamide
용매
HCID 8857Ethyl Acetate용매

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온도
60 °C

실험 절차

To a solution of 2-[2-(ethyloxy)ethyl]oxy-8-(methoxy)-9H-purin-6-amine trifluoroacetic acid salt (500 mg) in dry N,N-dimethylformamide (4.5 ml) at room temperature and under nitrogen was added potassium carbonate (0.75 g) in one go. The reaction was stirred at 60° C. for 1.5 hours. Tetrahydro-2H-pyran-4-ylmethyl methanesulfonate (0.29 g) was added in one portion and the reaction heated at 90° C. for 3 hours. The reaction was cooled to room temperature and then diluted with ethyl acetate (20 ml) and washed with water (15 ml). The organic layer was dried over magnesium sulphate, filtered and concentrated in vacuo. The product was purified by C18 reverse phase chromatography using water (containing 0.1% formic acid)-acetonitrile (containing 0.05% formic acid) as eluant (10-45%) to afford the title compound as a white solid (240 mg).

후처리

  1. temperaturethe reaction heated at 90° C. for 3 hours
  2. temperatureThe reaction was cooled to room temperature
  3. washwashed with water (15 ml)
  4. dry with materialThe organic layer was dried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe product was purified by C18 reverse phase chromatography

출처 및 근거

ORD 기록
ord-68757538abca40caabfac331585e1794
출처 데이터셋
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07977344B2

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