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

HRID 1517268

Reaktionsgleichung

Reaktionsgleichung von HRID 1517268
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

Komponenten

7

Edukt 4

HCID 8028Tetrahydrofuran2×HCID 121292,2-DiethoxyethanolHCID 31374DimethylacetamideHCID 5834662-Chloro-5-fluoropyrimidine

Produkt 2

HCID 684276832-(2,2-Diethoxyethoxy)-5-fluoropyrimidineAusbeute 67 %HCID 866458972-Chloro-5-(2,2-diethoxyethoxy)pyrimidineAusbeute 21 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-8ebeda40c0574f84982a4e30dc4f6227
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08232284B2

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