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Potassium Carbonate → 2-Butoxy-8-methoxy-9-(tetrahydrofuran-3-ylmethyl)-9H-purin-6-amine

HRID 1010932
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HRID 1010932 반응식
FC(F)(F)C(O)=O.[CH2:8]([O: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[CH2:37][CH2:36][O:35][CH2:34]1>CN(C)C=O>[CH2:8]([O: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[CH2:37][CH2:36][O:35][CH2:34]2)=[C:15]([NH2:24])[N:14]=1)[CH2:9][CH2:10][CH3:11]
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참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 141734223-(Bromomethyl)oxolaneHCID 178450370HCID 178450370, 화합물

생성물 1

HCID 576996032-Butoxy-8-methoxy-9-(tetrahydrofuran-3-ylmethyl)-9H-purin-6-amine수율 53%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
60 °C

실험 절차

2-Butoxy-8-methoxy-9H-purin-6-amine trifluoroacetate salt (0.20 g) was dissolved in anhydrous N,N-dimethylformamide (5 mL) was treated with anhydrous potassium carbonate (0.315 g), heated to 60° C. for 1 hour and then cooled to room temperature. To the above was added 3-(bromomethyl)tetrahydrofuran (0.103 g) and the reaction mixture heated at 50° C., overnight. The reaction mixture was quenched with water (25 mL) and extracted into ethyl acetate (3 times, 100 mL combined total volume). The combined organic phase was separated and passed through a hydrophobic frit to dry. The organic phase was stripped to give a gum which 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 white solid (97 mg).

후처리

  1. temperaturecooled to room temperature
  2. temperaturethe reaction mixture heated at 50° C., overnight
  3. customThe reaction mixture was quenched with water (25 mL)
  4. extractionextracted into ethyl acetate (3 times, 100 mL combined total volume)
  5. customThe combined organic phase was separated
  6. customto dry
  7. customto give a gum which
  8. customwas purified by C18 reverse phase chromatography

출처 및 근거

ORD 기록
ord-d9a3d438a04642ec8fdf822a6e281a42
출처 데이터셋
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07977344B2

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