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Sodium Hydroxide → 6-(Cyclohexyloxy)pyrimidine-4-carboxylic acid

HRID 1946691
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HRID 1946691 반응식
[CH:1]1([O:7][C:8]2[N:13]=[CH:12][N:11]=[C:10]([C:14]([O:16]C3CCCCC3)=[O:15])[CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>C1COCC1.CCO.O>[CH:1]1([O:7][C:8]2[N:13]=[CH:12][N:11]=[C:10]([C:14]([OH:16])=[O:15])[CH:9]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1
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참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 59446917Cyclohexyl 6-(cyclohexyloxy)pyrimidine-4-carboxylate

생성물 1

HCID 594470626-(Cyclohexyloxy)pyrimidine-4-carboxylic acid

시약·촉매·용매 1

HCID 18504229Ethanol tetrahydrofuran water용매

실험 절차

A solution of cyclohexyl 6-(cyclohexyloxy)pyrimidine-4-carboxylate (2.00 g; 6.57 mmol) in THF/EtOH/H2O (3/2/1, total volume 200 mL) was treated with a 5N solution of sodium hydroxide (3.94 ml; 19.7 mmol). The reaction mixture was stirred at room temperature for 2 h. The mixture was concentrated under vacuum and then water was added. The aqueous layer was washed with DCM then acidified to pH 5 by addition of 1N HCl solution. The aqueous layer was washed with EtOAc (150 mL), then lyophilized and the obtained solid was washed with DCM. The suspension was filtered off and the filtrate was concentrated under vacuum to afford the title compound as a beige solid.

후처리

  1. concentrationThe mixture was concentrated under vacuum
  2. additionwater was added
  3. washThe aqueous layer was washed with DCM
  4. additionthen acidified to pH 5 by addition of 1N HCl solution
  5. washThe aqueous layer was washed with EtOAc (150 mL)
  6. washthe obtained solid was washed with DCM
  7. filtrationThe suspension was filtered off
  8. concentrationthe filtrate was concentrated under vacuum

출처 및 근거

ORD 기록
ord-fbce2be32f634f41a35c45c0b230b6dc
출처 데이터셋
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08399448B2

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