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Phenol → 2-(2-chlorobenzoyl)-3-(2-phenoxy-pyrimidin-4-yl)-6,7-dihydro-5H-pyrazolo[1,2-a]pyrazol-1-one

HRID 1455262
ノート
印刷プレビュー

反応式

HRID 1455262 の反応式
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[Cl:10][C:11]1[CH:37]=[CH:36][CH:35]=[CH:34][C:12]=1[C:13]([C:15]1[C:22](=[O:23])[N:18]2[CH2:19][CH2:20][CH2:21][N:17]2[C:16]=1[C:24]1[CH:29]=[CH:28][N:27]=[C:26](S(C)(=O)=O)[N:25]=1)=[O:14]>C1COCC1.C([O-])(O)=O.[Na+]>[Cl:10][C:11]1[CH:37]=[CH:36][CH:35]=[CH:34][C:12]=1[C:13]([C:15]1[C:22](=[O:23])[N:18]2[CH2:19][CH2:20][CH2:21][N:17]2[C:16]=1[C:24]1[CH:29]=[CH:28][N:27]=[C:26]([O:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:25]=1)=[O:14]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 996PhenolHCID 24758Sodium hydrideHCID 574381012-(2-chlorobenzoyl)-3-(2-methanesulfonyl-pyrimidin-4-yl)-6,7-dihydro-5H-pyrazolo[1,2-a]pyrazol-1-one

生成物 1

HCID 114646442-(2-chlorobenzoyl)-3-(2-phenoxy-pyrimidin-4-yl)-6,7-dihydro-5H-pyrazolo[1,2-a]pyrazol-1-one

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回
HCID 516892
Sodium Bicarbonate
溶媒

実験手順

To a solution of phenol (0.04 g, 0.43 mmol) in THF (1 mL) is added sodium hydride (0.02 g of a 60% dispersion in mineral oil, 0.32 mmol). After stirring 5 min at room temperature a solution of 2-(2-chloro-benzoyl)-3-(2-methanesulfonyl-pyrimidin-4-yl)-6,7-dihydro-5H-pyrazolo[1,2-a]pyrazol-1-one, 24, (0.09 g, 0.21 mmol) in THF (2 mL) is added to the reaction mixture. After stirring 1.5 hours at room temperature, the mixture is diluted with aqueous saturated NaHCO3. The aqueous phase is extracted three times with CHCl3 and the combined organic phases are washed with aqueous saturated NaHCO3, dried (MgSO4), filtered and concentrated in vacuo. The crude residue is purified over silica (10% MeOH/CHCl3) to afford 30 mg of the desired product. 1H NMR (300 MHz, CDCl3) δ 8.77 (d, J=5.1 Hz, 1H), 8.04 (d, J=5.1 Hz, 1H), 7.49 (t, J=7.8 Hz, 1H), 7.41-7.20 (m, 9H), 4.00 (t, J=7.2 Hz, 2H), 3.95 (t, J=7.2 Hz, 2H), 2.54 (dddd, J=7.5, 7.5, 7.5, 7.5 Hz, 2H); ESI− MS: m/z (rel intensity) 431.1 (100, M+−H).

後処理

  1. additionis added to the reaction mixture
  2. extractionThe aqueous phase is extracted three times with CHCl3
  3. washthe combined organic phases are washed with aqueous saturated NaHCO3
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude residue is purified over silica (10% MeOH/CHCl3)

出典と根拠

ORDレコード
ord-a8d5aedf7aa546da9b8111f0b1e25d8f
出典データセット
uspto-grants-2009_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07482356B2

反応ノート

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