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Water → Ethyl 3-cyclopropyl-3-(6-(hydroxymethyl)pyrimidin-4-yl)propanoate

HRID 1049496
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HRID 1049496 반응식
[Si]([O:18][CH2:19][C:20]1[N:25]=[CH:24][N:23]=[C:22]([CH:26]([CH:33]2[CH2:35][CH2:34]2)[CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH:21]=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>C1COCC1>[CH:33]1([CH:26]([C:22]2[CH:21]=[C:20]([CH2:19][OH:18])[N:25]=[CH:24][N:23]=2)[CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:34][CH2:35]1
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참가 물질

5

반응물 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 131736020Ethyl 3-(6-(((tert-butyldiphenylsilyl)oxy)methyl)pyrimidin-4-yl)-3-cyclopropylpropanoate

생성물 1

HCID 117759635Ethyl 3-cyclopropyl-3-(6-(hydroxymethyl)pyrimidin-4-yl)propanoate수율 71.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of ethyl 3-(6-(((tert-butyldiphenylsilyl)oxy)methyl)pyrimidin-4-yl)-3-cyclopropylpropanoate (6.70 g) in THF (50 mL) was added a 1.0 M solution of tetrabutylammonium fluoride in THF (27.4 mL) at room temperature, and the mixture was directly stirred for 5 min. Water was added to the reaction mixture at room temperature, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (2.44 g) as a yellow oil.

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-3cfb3e04dfb2402fbe5829835701e665
출처 데이터셋
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09382188B2

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