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Water → Tert-butyl 3-(5-bromopyrimidin-2-yl)oxy-2,2-dimethylpropanoate

HRID 623937
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HRID 623937 반응식
[Br:1][C:2]1[CH:3]=C[C:5](Cl)=[N:6][CH:7]=1.[OH:9][CH2:10][C:11]([CH3:20])([CH3:19])[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].[H-].[Na+].O.C[N:25](C)C=O>>[Br:1][C:2]1[CH:7]=[N:6][C:5]([O:9][CH2:10][C:11]([CH3:20])([CH3:19])[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[N:25][CH:3]=1
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참가 물질

6

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HCID 962WaterHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 27344145-Bromo-2-chloropyridineHCID 54272639Tert-butyl 3-hydroxy-2,2-dimethylpropanoate

생성물 1

HCID 67972905Tert-butyl 3-(5-bromopyrimidin-2-yl)oxy-2,2-dimethylpropanoate

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온도
50 °C

실험 절차

In N,N-dimethylformamide (10 mL) were dissolved 5-bromo-2-chloropyridine (1000 mg) and tert-butyl 3-hydroxy-2,2-dimethylpropanoate (991 mg), and 60% sodium hydride (248 mg) was added to the solution under ice-cooling. The reaction mixture was stirred at room temperature for 6 hours, at 50° C. for 1 hour and 45 minutes, and then, at room temperature overnight. Water was added to the reaction mixture under ice-cooling, and the mixture was extracted with ether. The organic layer was separated, washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=100:0 to 95:5) to obtain tert-butyl 3-(5-bromopyrimidin-2-yl)oxy-2,2-dimethylpropanoate (1.048 g).

후처리

  1. additionwas added to the solution under ice-
  2. temperaturecooling
  3. customat room temperature
  4. customovernight
  5. temperaturecooling
  6. extractionthe mixture was extracted with ether
  7. customThe organic layer was separated
  8. washwashed with saturated brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customThe obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=100:0 to 95:5)

출처 및 근거

ORD 기록
ord-61eabace70ee45f9a9f7eb6bdf4c80ca
출처 데이터셋
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09302996B2

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