Sodium hydride → HCID 86695236、化合物

HRID 1504081ノート

反応式

HRID 1504081 の反応式
Cl[C:2]1[C:3]2[CH:10]=[C:9]([CH2:11][CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[S:8][C:4]=2[N:5]=[CH:6][N:7]=1.[H-].[Na+].[CH3:23][N:24]([CH3:32])[CH:25]1[CH2:30][CH2:29][CH:28]([OH:31])[CH2:27][CH2:26]1>C1COCC1>[CH3:23][N:24]([CH3:32])[CH:25]1[CH2:30][CH2:29][CH:28]([O:31][C:2]2[C:3]3[CH:10]=[C:9]([CH2:11][CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[S:8][C:4]=3[N:5]=[CH:6][N:7]=2)[CH2:27][CH2:26]1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 18702099trans-4-(Dimethylamino)cyclohexanolHCID 86695235HCID 86695235、化合物

生成物 1

HCID 86695236HCID 86695236、化合物収率 52%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of tert-butyl N-(2-[4-chlorothieno[2,3-d]pyrimidin-6-yl]ethyl)carbamate (100 mg, 0.32 mmol, 1.00 equiv) in freshly distilled THF (20 mL) was added sodium hydride (64 mg, 1.6 mmol, 5.0 equiv, 60% dispersion in mineral oil) at 0° C. under nitrogen. After stirring for 30 min at room temperature, a solution of 4-(dimethylamino)cyclohexan-1-ol (50 mg, 0.35 mmol, 1.06 equiv) was added and stirred overnight at room temperature. The reaction was then quenched by the addition of brine and extracted with EtOAc. The organic layers was combined and dried over anhydrous sodium sulfate. After filtration and concentration, the residue was applied onto a silica gel column with DCM/MeOH (50:1-30:1) to provide 70 mg (52%) of tert-butyl N-[2-(4-[[4-(dimethylamino)cyclohexyl]oxy]thieno[2,3-d]pyrimidin-6-yl)ethyl]carbamate as a light yellow solid. MS (ES): m/z 421 (M+H)+.

後処理

  1. stirringstirred overnight at room temperature
  2. customThe reaction was then quenched by the addition of brine
  3. extractionextracted with EtOAc
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationAfter filtration and concentration

出典と根拠

ORDレコード
ord-c220d2064788407c8d2662360e30d36d
出典データセット
uspto-grants-2015_12
特許番号
US09212190B2

反応ノート

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