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

HRID 1010996
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HRID 1010996 반응식
F[C:2](F)(F)[C:3](O)=O.C(N[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)CCC.[C:25](=[O:28])([O-])[O-].[K+].[K+].CS(O[CH2:36][CH:37]1[CH2:41][CH2:40][O:39][CH2:38]1)(=O)=O.[CH3:42]N(C)C=O>>[CH2:25]([O:28][C:13]1[N:21]=[C:20]2[C:16]([N:17]=[C:18]([O:22][CH3:23])[N:19]2[CH2:36][CH:37]2[CH2:41][CH2:40][O:39][CH2:38]2)=[C:15]([NH2:24])[N:14]=1)[CH2:42][CH2:2][CH3:3]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 22273010(Tetrahydrofuran-3-yl)methyl methanesulfonateHCID 178448879HCID 178448879, 화합물

생성물 1

HCID 576996032-Butoxy-8-methoxy-9-(tetrahydrofuran-3-ylmethyl)-9H-purin-6-amine

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온도
60 °C

실험 절차

A stirring mixture of N2-butyl-8-methoxy-9H-purine-2,6-diamine trifluoroacetic acid salt (3.25 gm) and potassium carbonate (3.83 gm) in dry N,N-dimethylformamide (30 ml) was heated with stirring at 60° C. for 1 h. Tetrahydro-3-furanylmethyl methanesulfonate (2 gm, Isomer 1) was added and the stirring mixture heated at 90° C. for 3 h. The solvent was evaporated, water was added and the mixture extracted three times with ethyl acetate. The combined extracts were washed with water then brine, dried by passing through a hydrophobic frit and stripped to give an orange solid. This was purified by C18 reverse phase chromatography using water (0.1% formic acid)-acetonitrile (0.05% formic acid) as eluent (20-60%) and the appropriate fractions combined and evaporated to give the title compound as a light orange solid, yield 1.56 gm.

후처리

  1. temperaturewas heated
  2. temperaturethe stirring mixture heated at 90° C. for 3 h
  3. customThe solvent was evaporated
  4. additionwater was added
  5. extractionthe mixture extracted three times with ethyl acetate
  6. washThe combined extracts were washed with water
  7. dry with materialbrine, dried
  8. customto give an orange solid
  9. customThis was purified by C18 reverse phase chromatography
  10. customevaporated

출처 및 근거

ORD 기록
ord-cc4e0d66db6d4876a914a1f966c27c98
출처 데이터셋
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07977344B2

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