Sodium Thiosulfate → 4-[4-(2-Fluoro-phenyl)-2-oxo-2H-pyrimidin-1-yl]-butyraldehyde

HRID 1514435Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1514435
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][N:11]([CH2:14][CH2:15][CH2:16][CH2:17][OH:18])[C:10](=[O:19])[N:9]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][N:11]([CH2:14][CH2:15][CH2:16][CH:17]=[O:18])[C:10](=[O:19])[N:9]=1

Komponenten

5

Edukt 3

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 592427824-(2-Fluoro-phenyl)-1-(4-hydroxy-butyl)-1H-pyrimidin-2-one

Produkt 1

HCID 592428054-[4-(2-Fluoro-phenyl)-2-oxo-2H-pyrimidin-1-yl]-butyraldehydeAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 4-(2-fluoro-phenyl)-1-(4-hydroxy-butyl)-1H-pyrimidin-2-one (80 mg, 0.30 mmol) in DCM (8 ml), the solution at 0° C., solid Dess Martin periodinane (380 mg, 0.61 mmol) was added portionwise. The mixture was stirred at room temperature for 1 hour. Na2S2O3 was added and the mixture was extracted with DCM; the organic layer was dried (Na2SO4), filtered and evaporated. The crude was purified by flash chromatography with ethyl acetate to give 50 mg of the title compound as a green solid (64% yield).

Aufarbeitung

  1. extractionthe mixture was extracted with DCM
  2. dry with materialthe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude was purified by flash chromatography with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-1764c00be0d14417a08799e08551746d
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08222266B2

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