Sodium hydride → (S)-1-(2-(tert-butyldimethylsilyloxy)ethyl)-4-isopropyl-3-(3-(4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)imidazolidin-2-one

HRID 539029ノート

反応式

HRID 539029 の反応式
[CH:1]([C@@H:4]1[N:8]([C:9]2[CH:14]=[CH:13][N:12]3[N:15]=[CH:16][C:17]([C:18]4[CH:23]=[CH:22][C:21]([C:24]5[N:28]=[CH:27][N:26]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])[N:25]=5)=[CH:20][CH:19]=4)=[C:11]3[N:10]=2)[C:7](=[O:37])[NH:6][CH2:5]1)([CH3:3])[CH3:2].[H-].[Na+].Br[CH2:41][CH2:42][O:43][Si:44]([C:47]([CH3:50])([CH3:49])[CH3:48])([CH3:46])[CH3:45]>>[Si:44]([O:43][CH2:42][CH2:41][N:6]1[CH2:5][C@H:4]([CH:1]([CH3:3])[CH3:2])[N:8]([C:9]2[CH:14]=[CH:13][N:12]3[N:15]=[CH:16][C:17]([C:18]4[CH:23]=[CH:22][C:21]([C:24]5[N:28]=[CH:27][N:26]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:34])([CH3:35])[CH3:36])[N:25]=5)=[CH:20][CH:19]=4)=[C:11]3[N:10]=2)[C:7]1=[O:37])([C:47]([CH3:50])([CH3:49])[CH3:48])([CH3:46])[CH3:45]

参加物

4

反応物 3

HCID 24758Sodium hydrideHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilaneHCID 67033259(S)-5-isopropyl-1-(3-(4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)imidazolidin-2-one

生成物 1

HCID 67034472(S)-1-(2-(tert-butyldimethylsilyloxy)ethyl)-4-isopropyl-3-(3-(4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)imidazolidin-2-one収率 60%

実験手順

To a solution of (S)-5-isopropyl-1-(3-(4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)imidazolidin-2-one (0.23 g, 0.443 mmol) at 0° C. was added sodium hydride (0.0355 g, 0.887 mmol) and the reaction stirred 10 minutes. (2-Bromoethoxy)(tert-butyl)dimethylsilane (0.212 g, 0.887 mmol) was added and the reaction stirred for 2 hours while warming to ambient temperature. The reaction was poured onto water and extracted into EtOAc. The combined organic layers were washed with water, brine, dried over magnesium sulfate and concentrated in vacuo. The crude material was chromatographed using 20% EtOAc/dichloromethane as eluent to yield (S)-1-(2-(tert-butyldimethylsilyloxy)ethyl)-4-isopropyl-3-(3-(4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)imidazolidin-2-one (0.18 g, 60%).

後処理

  1. stirringthe reaction stirred for 2 hours
  2. additionThe reaction was poured onto water
  3. extractionextracted into EtOAc
  4. washThe combined organic layers were washed with water, brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe crude material was chromatographed

出典と根拠

ORDレコード
ord-8e6fc81ff0304e4e8ac6e87f40990419
出典データセット
uspto-grants-2014_10
特許番号
US08865726B2

反応ノート

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