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Water → 2-(2,6-Dimethylpyridin-4-yl)-7-(2-isopropoxyethoxy)-5-methoxyquinazolin-4(3H)-one

HRID 591828
ノート
印刷プレビュー

反応式

HRID 591828 の反応式
[H-].[Na+].[CH:3]([O:6][CH2:7][CH2:8][OH:9])([CH3:5])[CH3:4].[CH3:10][C:11]1[CH:16]=[C:15]([C:17]2[NH:26][C:25](=[O:27])[C:24]3[C:19](=[CH:20][C:21](F)=[CH:22][C:23]=3[O:28][CH3:29])[N:18]=2)[CH:14]=[C:13]([CH3:31])[N:12]=1.O>CS(C)=O>[CH3:10][C:11]1[CH:16]=[C:15]([C:17]2[NH:26][C:25](=[O:27])[C:24]3[C:19](=[CH:20][C:21]([O:9][CH2:8][CH2:7][O:6][CH:3]([CH3:5])[CH3:4])=[CH:22][C:23]=3[O:28][CH3:29])[N:18]=2)[CH:14]=[C:13]([CH3:31])[N:12]=1
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 4

HCID 962WaterHCID 7996IsopropylethanediolHCID 24758Sodium hydrideHCID 1363480402-(2,6-dimethyl-pyridin-4-yl)-7-fluoro-5-methoxy-3H-quinazolin-4-one

生成物 1

HCID 1359390732-(2,6-Dimethylpyridin-4-yl)-7-(2-isopropoxyethoxy)-5-methoxyquinazolin-4(3H)-one

試薬・触媒・溶媒 1

HCID 679
Dimethyl Sulfoxide
溶媒

実験手順

To a suspension of sodium hydride (60% suspension in mineral oil, 0.24 g, 6.00 mmol) in anhydrous DMSO (10 mL) was added 2-isopropoxy-ethanol at room temperature under nitrogen. The mixture was stirred for 20 minutes at room temperature, then 2-(2,6-dimethyl-pyridin-4-yl)-7-fluoro-5-methoxy-3H-quinazolin-4-one (0.30 g, 1.00 mmol) was added and the reaction mixture was stirred at 80° C. for 16 hours, then cooled to room temperature. Water (50 mL) was added, and the mixture was extracted with a mixture of ethyl acetate and THF (4:1, 200 mL). The organic phase was washed with brine and dried over anhydrous sodium sulfate. Solvent was evaporated, and the crude compound was purified by the Simpliflash system (3:15:82 methanol, ethyl acetate and dichloromethane as eluent) to give the title compound as a white solid. Yield: 127 mg (33%). MP 188-189° C. 1H NMR (400 MHz, CDCl3): δ 11.14 (br s, 1H), 7.72 (s, 2H), 6.86 (d, J=2.34 Hz, 1H), 6.59 (d, J=2.34 Hz, 1H), 4.35-4.15 (m, 2H), 3.97 (s, 3H), 3.89-3.79 (m, 2H), 3.78-3.64 (m, 1H), 2.66 (s, 6H), 1.23 (d, J=5.85 Hz, 6H). MS (ES+) m/z: 384.20 (100%).

後処理

  1. stirringthe reaction mixture was stirred at 80° C. for 16 hours
  2. temperaturecooled to room temperature
  3. extractionthe mixture was extracted with a mixture of ethyl acetate and THF (4:1, 200 mL)
  4. washThe organic phase was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customSolvent was evaporated
  7. customthe crude compound was purified by the Simpliflash system (3:15:82 methanol, ethyl acetate and dichloromethane as eluent)

出典と根拠

ORDレコード
ord-f6a9210b7945489aa66d15258aa55ab9
出典データセット
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09238640B2

反応ノート

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