反応式
[CH:1]1([N:5]2[CH2:11][CH2:10][C:9]3[CH:12]=[C:13]([OH:16])[CH:14]=[CH:15][C:8]=3[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1.[H-].[Na+].Br[C:20]1[CH:21]=[N:22][C:23]([C:26]#[N:27])=[N:24][CH:25]=1>N1C=CC=CC=1.[Cu]Br>[CH:1]1([N:5]2[CH2:6][CH2:7][C:8]3[CH:15]=[CH:14][C:13]([O:16][C:20]4[CH:21]=[N:22][C:23]([C:26]#[N:27])=[N:24][CH:25]=4)=[CH:12][C:9]=3[CH2:10][CH2:11]2)[CH2:4][CH2:3][CH2:2]1参加物
反応物 3
生成物 1
試薬・触媒・溶媒 2
反応条件
- 温度
- 0 °C
実験手順
3-Cyclobutyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-ol (E3) (1.81 g, 8.33 mmol) was dissolved in pyridine (40 ml) and sodium hydride (60% in mineral oil, 0.40 g, 10.0 mmol) was added with stirring under argon at 0° C. The mixture was left to stir for 5 minutes. Copper (I) bromide (1.68 g, 11.7 mmol) was added and the mixture allowed to warm to room temperature over 30 minutes. 5-Bromo-2-pyrimidinecarbonitrile (D38) (2.30 g, 12.5 mmol) in pyridine (8 ml) was added and the mixture heated at 100° C. for 1 hour. The mixture was allowed to cool to room temperature and the solvent removed in vacuo. The crude product was purified by column chromatography, eluting with a mixture of 0.880 ammonia:methanol:dichloromethane (0.2:1.8:98) to afford the title compound (E177a); MS (ES+) m/e 321 [M+H]+.
後処理
- waitThe mixture was left
- stirringto stir for 5 minutes
- temperatureto warm to room temperature over 30 minutes
- temperaturethe mixture heated at 100° C. for 1 hour
- temperatureto cool to room temperature
- customthe solvent removed in vacuo
- customThe crude product was purified by column chromatography
- washeluting with a mixture of 0.880 ammonia:methanol:dichloromethane (0.2:1.8:98)
出典と根拠
- ORDレコード
- ord-22bcbe3819914551a7ef50d89cc84740
- 出典データセット
- uspto-grants-2012_06
- 特許番号
- US08207331B2
関連ノート
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