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Water → 4-(benzyloxy)-2-(1H-pyrazol-1-yl)pyrimidine-5-carboxylic acid

HRID 1470304
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HRID 1470304 반응식
[CH2:1]([O:8][C:9]1[C:14]([C:15]([O:17]CC2C=CC=CC=2)=[O:16])=[CH:13][N:12]=[C:11]([N:25]2[CH:29]=[CH:28][CH:27]=[N:26]2)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1COCC1.O.[OH-].[K+]>CCO>[CH2:1]([O:8][C:9]1[C:14]([C:15]([OH:17])=[O:16])=[CH:13][N:12]=[C:11]([N:25]2[CH:29]=[CH:28][CH:27]=[N:26]2)[N:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
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참가 물질

6

반응물 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 67459462Benzyl 4-(benzyloxy)-2-(1H-pyrazol-1-yl)pyrimidine-5-carboxylate

생성물 1

HCID 674594834-(benzyloxy)-2-(1H-pyrazol-1-yl)pyrimidine-5-carboxylic acid수율 13%

시약·촉매·용매 1

HCID 702
Ethanol
용매

실험 절차

To a solution of benzyl 4-(benzyloxy)-2-(1H-pyrazol-1-yl)pyrimidine-5-carboxylate, 2-d, (2 g crude) in EtOH(20 ml)/THF (20 ml)/water (20 ml) was added KOH (0.87 g, 15.5 mmol). The mixture was stirred at room temperature for 12 hours. The mixture was then concentrated under vacuum and the residue was diluted with water and basified to pH=2 with HCl followed by extraction with ethyl acetate. The organic layer was brine washed, dried over sodium sulfate and concentrated under vacuum. The residue was purified on a silica gel column with the eluent of petroleum ether/ethyl acetate=7/1 to afford the compound 2-e (200 mg, 13%).

후처리

  1. concentrationThe mixture was then concentrated under vacuum
  2. additionthe residue was diluted with water and basified to pH=2 with HCl
  3. extractionfollowed by extraction with ethyl acetate
  4. washwashed
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified on a silica gel column with the eluent of petroleum ether/ethyl acetate=7/1

출처 및 근거

ORD 기록
ord-ac54a65de9b4495aa376192c53b5c98a
출처 데이터셋
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09006433B2

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