Chlorine → 1-(2,4-Dichloropyrimidin-5-yl)ethan-1-one

HRID 750485노트

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HRID 750485 반응식
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([CH:9]([OH:11])[CH3:10])=[CH:4][N:3]=1.CC1(C)N([O])C(C)(C)CCC1.C(=O)(O)[O-].[Na+].ClCl>C(Cl)Cl.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.O.C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([C:9](=[O:11])[CH3:10])=[CH:4][N:3]=1

참가 물질

9

반응물 4

HCID 24526ChlorineHCID 516892Sodium BicarbonateHCID 2724126TempoHCID 151416481-(2,4-Dichloropyrimidin-5-yl)ethan-1-ol

생성물 1

HCID 212747081-(2,4-Dichloropyrimidin-5-yl)ethan-1-one

시약·촉매·용매 4

HCID 70681Tetrabutylammonium Chloride촉매HCID 962Water용매2회HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

To a stirred suspension of 1-(2,4-dichloro-pyrimidin-5-yl)-ethanol (Example 20, 1.00 g, 5.2 mmol) in a mixture of methylene chloride (30 mL), THF (8 mL) and water (2 mL), tetrabutylammonium chloride (Aldrich, 50 mg, 0.15 mmol), TEMPO (Aldrich, 9 mg, 0.05 mmol) and sodium bicarbonate (208 mg, 2.48 mmol) were added and the mixture was cooled to 0° C. To the stirred mixture, colorex (Aldrich; active Cl2, 10-13%; 3.75 mL) was added and the mixture was stirred for 2 hours at 0° C. Water (10 mL) was added and the organic layer was separated and dried over sodium sulfate. Removal of solvent gave an oil which was purified by silica gel chromatography (1% MeOH/CH2Cl2) to yield a colorless oil. 232 mg, 23%. MS (M+H)+, 191.

후처리

  1. additionwere added
  2. customthe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. customRemoval of solvent
  5. customgave an oil which
  6. customwas purified by silica gel chromatography (1% MeOH/CH2Cl2)
  7. customto yield a colorless oil

출처 및 근거

ORD 기록
ord-08afe15dbd4d464195433ac037f25b92
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07405220B2

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