Potassium Carbonate → N2-Butyl-8-methoxy-9-(tetrahydro-2H-pyran-3-ylmethyl)-9H-purine-2,6-diamine

HRID 1010931노트

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HRID 1010931 반응식
FC(F)(F)C(O)=O.[CH2:8]([NH:12][C:13]1[N:21]=[C:20]2[C:16]([N:17]=[C:18]([O:22][CH3:23])[NH:19]2)=[C:15]([NH2:24])[N:14]=1)[CH2:9][CH2:10][CH3:11].C(=O)([O-])[O-].[K+].[K+].Br[CH2:32][CH:33]1[CH2:38][CH2:37][CH2:36][O:35][CH2:34]1>CN(C)C=O.C(OCC)(=O)C>[CH2:8]([NH:12][C:13]1[N:21]=[C:20]2[C:16]([N:17]=[C:18]([O:22][CH3:23])[N:19]2[CH2:32][CH:33]2[CH2:38][CH2:37][CH2:36][O:35][CH2:34]2)=[C:15]([NH2:24])[N:14]=1)[CH2:9][CH2:10][CH3:11]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 226172573-(Bromomethyl)oxaneHCID 178448879HCID 178448879, 화합물

생성물 1

HCID 57699736N2-Butyl-8-methoxy-9-(tetrahydro-2H-pyran-3-ylmethyl)-9H-purine-2,6-diamine수율 47.1%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매2회HCID 8857Ethyl Acetate용매

반응 조건

온도
60 °C

실험 절차

To a solution of N2-butyl-8-methoxy-9H-purine-2,6-diamine trifluoroacetic acid salt (100 mg) in dry N,N-dimethylformamide (1 ml) at room temperature and under nitrogen was added potassium carbonate (158 mg) in one go. The reaction was stirred at 60° C. for 1.5 hours and then cooled to 50° C. A solution of 3-(bromomethyl)tetrahydro-2H-pyran (56 mg) in dry N,N-dimethylformamide (0.3 ml) was added in one go and the reaction heated at 50° C. for 16 hours. The reaction was diluted with ethyl acetate (15 ml) and washed with water (5 ml). The organic layer was separated, 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 (20-60%) to afford the title compound as a yellow oil (45 mg).

후처리

  1. temperaturecooled to 50° C
  2. temperaturethe reaction heated at 50° C. for 16 hours
  3. washwashed with water (5 ml)
  4. customThe organic layer was separated
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe product was purified by C18 reverse phase chromatography

출처 및 근거

ORD 기록
ord-6cb6283218744de98923256f06e5521f
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07977344B2

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