Dimethylformamide → HCID 178425937, 화합물

HRID 447690노트

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HRID 447690 반응식
[CH3:1][C:2]1[CH:3]=[C:4]([SH:8])[CH:5]=[CH:6][CH:7]=1.CN(C=O)C.[H-].[Na+].[Si:16]([O:23][C@@H:24]1[C@H:28]([CH2:29][O:30][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32])[CH2:27][C@@H:26]([O:38][C:39]2[N:47]=[CH:46][N:45]=[C:44]3[C:40]=2[N:41]=[C:42](I)[N:43]3C2CCCCO2)[CH2:25]1)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]>>[Si:16]([O:23][C@@H:24]1[C@H:28]([CH2:29][O:30][Si:31]([C:34]([CH3:35])([CH3:36])[CH3:37])([CH3:32])[CH3:33])[CH2:27][C@@H:26]([O:38][C:39]2[N:47]=[CH:46][N:45]=[C:44]3[C:40]=2[N:41]=[C:42]([S:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[CH:3]=2)[NH:43]3)[CH2:25]1)([C:19]([CH3:20])([CH3:21])[CH3:22])([CH3:17])[CH3:18]

참가 물질

5

반응물 4

HCID 6228DimethylformamideHCID 79303-ThiocresolHCID 24758Sodium hydrideHCID 667979406-{[(1R,3S,4S)-3-{[tert-butyl(dimethyl)silyl]oxy}-4-({[tert-butyl(dimethyl)silyl]-oxy}methyl)cyclopentyl]oxy}-8-iodo-9-(tetrahydro-2H-pyran-2-yl)-9H-purine

생성물 1

HCID 178425937HCID 178425937, 화합물수율 82.1%

실험 절차

To a solution of 3-methylbenzenethiol (0.55 mL, 0.0046 mol) in DMF (10 mL, 0.2 mol) was added sodium hydride (0.093 g, 0.0023 mol). The mixture was stirred at room temperature for 10 minutes and then 6-{[(1R,3S,4S)-3-{[tert-butyl(dimethyl)silyl]oxy}-4-({[tert-butyl(dimethyl)silyl]oxy}methyl)cyclopentyl]oxy}-8-iodo-9-(tetrahydro-2H-pyran-2-yl)-9H-purine (400 mg, 0.0006 mol) (Example 115, steps a-b) was added and the solution was heated at 150° C. for 8 hours. The reaction was cooled, quenched by addition of water and the mixture was extracted with ethyl acetate, washed with water, brine, dried (Na2SO4), filtered and concentrated. The residue was purified by flash chromatography (0 to 30% ethyl acetate/hexanes) to obtain 296 mg (80%) of the title compound.

후처리

  1. temperaturethe solution was heated at 150° C. for 8 hours
  2. temperatureThe reaction was cooled
  3. customquenched by addition of water
  4. extractionthe mixture was extracted with ethyl acetate
  5. washwashed with water, brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by flash chromatography (0 to 30% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-8029dc66c5e04572a854d89a671f3982
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08481550B2

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