Tetrahydrofuran → 2-(2,2-Diethoxyethoxy)-5-fluoropyrimidine

HRID 81629

반응식

HRID 81629 반응식
O1CCCC1.[CH2:6]([O:8][CH:9]([O:12][CH2:13][CH3:14])[CH2:10][OH:11])[CH3:7].CN(C)C(=O)C.[Cl:21][C:22]1[N:27]=[CH:26][C:25]([F:28])=[CH:24][N:23]=1>O>[CH2:6]([O:8][CH:9]([O:12][CH2:13][CH3:14])[CH2:10][O:11][C:22]1[N:27]=[CH:26][C:25]([F:28])=[CH:24][N:23]=1)[CH3:7].[Cl:21][C:22]1[N:27]=[CH:26][C:25]([O:11][CH2:10][CH:9]([O:12][CH2:13][CH3:14])[O:8][CH2:6][CH3:7])=[CH:24][N:23]=1

참가 물질

7

반응물 4

HCID 8028Tetrahydrofuran2회HCID 121292,2-DiethoxyethanolHCID 31374DimethylacetamideHCID 5834662-Chloro-5-fluoropyrimidine

생성물 2

HCID 684276832-(2,2-Diethoxyethoxy)-5-fluoropyrimidine수율 67%HCID 866458972-Chloro-5-(2,2-diethoxyethoxy)pyrimidine수율 21%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

With cooling with ice, a tetrahydrofuran solution (2 ml) of 2,2-diethoxyethanol (668 mg, 4.98 mmol) was added to a mixed tetrahydrofuran (4 ml)/N,N-dimethylacetamide (2 ml) solution of 2-chloro-5-fluoropyrimidine (600 mg, 4.53 mmol), and stirred under a nitrogen atmosphere for 1 hour. Water was added to the reaction solution, and extracted with ethyl acetate. Next, the organic layer was washed with saturated saline water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (Moritex, acetone:hexane=1:25) to obtain 2-(2,2-diethoxyethoxy)-5-fluoropyrimidine (699 mg, yield: 67%) as a colorless oil, and 2-chloro-5-(2,2-diethoxyethoxy)pyrimidine (233 mg, 21%) as a colorless solid.

후처리

  1. temperatureWith cooling with ice
  2. extractionextracted with ethyl acetate
  3. washNext, the organic layer was washed with saturated saline water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (Moritex, acetone:hexane=1:25)

출처 및 근거

ORD 기록
ord-e27b373c1e6a4e388b8ecb2abf664fe7
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846700B2

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