Dimethylformamide → HCID 178425937、化合物
反応式
[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]参加物
実験手順
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.
後処理
- temperaturethe solution was heated at 150° C. for 8 hours
- temperatureThe reaction was cooled
- customquenched by addition of water
- extractionthe mixture was extracted with ethyl acetate
- washwashed with water, brine
- dry with materialdried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified by flash chromatography (0 to 30% ethyl acetate/hexanes)
出典と根拠
- ORDレコード
- ord-8029dc66c5e04572a854d89a671f3982
- 出典データセット
- uspto-grants-2013_07
- 特許番号
- US08481550B2
反応ノート
読み込み中…