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Sodium Hydroxide → 3-Hydroxy-1-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]cyclobutylacetonitrile

HRID 1426298
ノート
印刷プレビュー

反応式

HRID 1426298 の反応式
[Si]([O:18][CH:19]1[CH2:22][C:21]([CH2:45][C:46]#[N:47])([N:23]2[CH:27]=[C:26]([C:28]3[C:29]4[CH:36]=[CH:35][N:34]([CH2:37][O:38][CH2:39][CH2:40][Si:41]([CH3:44])([CH3:43])[CH3:42])[C:30]=4[N:31]=[CH:32][N:33]=3)[CH:25]=[N:24]2)[CH2:20]1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[OH-].[Na+]>C(O)C.O>[OH:18][CH:19]1[CH2:22][C:21]([CH2:45][C:46]#[N:47])([N:23]2[CH:27]=[C:26]([C:28]3[C:29]4[CH:36]=[CH:35][N:34]([CH2:37][O:38][CH2:39][CH2:40][Si:41]([CH3:42])([CH3:44])[CH3:43])[C:30]=4[N:31]=[CH:32][N:33]=3)[CH:25]=[N:24]2)[CH2:20]1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 14798Sodium HydroxideHCID 67955173{3-{[tert-butyl(diphenyl)silyl]oxy}-1-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]cyclobutyl}acetonitrile

生成物 1

HCID 670171833-Hydroxy-1-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]cyclobutylacetonitrile収率 88.7%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒
HCID 962
Water
溶媒
2 回

実験手順

To {3-{[tert-butyl(diphenyl)silyl]oxy}-1-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]cyclobutyl}acetonitrile (2.85 g, 4.30 mmol) in ethanol (120 mL) was added 5.0M sodium hydroxide in water (29 mL, 150 mmol). The reaction was stirred for 3 hours and diluted with water. The ethanol was removed under reduced pressure. The aqueous layer was extracted with ethyl acetate three times. The combine organic solutions were washed with brine, dried over Na2SO4, filtered and concentrated. The crude was purified with silica gel column eluting with a gradient from 0-10% MeOH/DCM to give of the product (1.62 g, 88%) as .off-white foam. LCMS (M+H)+: 425.2.

後処理

  1. customThe ethanol was removed under reduced pressure
  2. extractionThe aqueous layer was extracted with ethyl acetate three times
  3. washThe combine organic solutions were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude was purified with silica gel column
  8. washeluting with a gradient from 0-10% MeOH/DCM

出典と根拠

ORDレコード
ord-62a1ff1a224f40fb8f60e8bf2a8dd24b
出典データセット
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08933085B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート