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Hydrochloric Acid → Ethyl 3-cyclopropyl-3-(6-((6-(2-fluoro-5-methoxyphenyl)-5-isobutoxypyridin-3-yl)methoxy)pyrimidin-4-yl)propanoate

HRID 709766
ノート
印刷プレビュー

反応式

HRID 709766 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[N:15]=[CH:14][C:13]([CH2:16][OH:17])=[CH:12][C:11]=1[O:18][CH2:19][CH:20]([CH3:22])[CH3:21].Cl[C:24]1[N:29]=[CH:28][N:27]=[C:26]([CH:30]([CH:37]2[CH2:39][CH2:38]2)[CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH:25]=1.[H-].[Na+].Cl.C(=O)([O-])O.[Na+]>C1COCC1>[CH:37]1([CH:30]([C:26]2[CH:25]=[C:24]([O:17][CH2:16][C:13]3[CH:14]=[N:15][C:10]([C:3]4[CH:4]=[C:5]([O:8][CH3:9])[CH:6]=[CH:7][C:2]=4[F:1])=[C:11]([O:18][CH2:19][CH:20]([CH3:22])[CH3:21])[CH:12]=3)[N:29]=[CH:28][N:27]=2)[CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH2:39][CH2:38]1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 117760030Ethyl 3-(6-chloropyrimidin-4-yl)-3-cyclopropylpropanoateHCID 117760274(6-(2-Fluoro-5-methoxyphenyl)-5-isobutoxypyridin-3-yl)methanol

生成物 1

HCID 117759893
Ethyl 3-cyclopropyl-3-(6-((6-(2-fluoro-5-methoxyphenyl)-5-isobutoxypyridin-3-yl)methoxy)pyrimidin-4-yl)propanoate
収率 88.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Under an argon atmosphere, to a solution of (6-(2-fluoro-5-methoxyphenyl)-5-isobutoxypyridin-3-yl)methanol (587 mg) and ethyl 3-(6-chloropyrimidin-4-yl)-3-cyclopropylpropanoate (587 mg) in THF (9.6 mL) was added 60% sodium hydride (100 mg) at 0° C., and the mixture was stirred at room temperature for 4 hr. 1N Hydrochloric acid was added to the reaction mixture at 0° C., and the mixture was neutralized with saturated aqueous sodium hydrogen carbonate solution. The reaction mixture was extracted with ethyl acetate, and the extract was washed with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (890 mg) as a colorless oil.

後処理

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. washthe extract was washed with water and saturated brine
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-d5176756280f40e6a7efc7b14fd17d4e
出典データセット
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09181186B2

反応ノート

読み込み中…

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