N,N-Diethylaniline → 4-Chloro-5-methoxy-2-(methylsulfanyl)pyrimidine

HRID 658083Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 658083
[CH3:1][O:2][C:3]1[C:4](O)=[N:5][C:6]([S:9][CH3:10])=[N:7][CH:8]=1.P(Cl)(Cl)([Cl:14])=O.C(N(CC)C1C=CC=CC=1)C>C(#N)C>[Cl:14][C:4]1[C:3]([O:2][CH3:1])=[CH:8][N:7]=[C:6]([S:9][CH3:10])[N:5]=1

Komponenten

5

Edukt 3

HCID 7061N,N-DiethylanilineHCID 24813Phosphorus oxychlorideHCID 178493801HCID 178493801, Verbindung

Produkt 1

HCID 2435114-Chloro-5-methoxy-2-(methylsulfanyl)pyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

5-Methoxy-2-methylsulfanyl-pyrimidin-4-ol (250 mg) is dissolved in acetonitrile (7 ml) and thereto are added phosphorus oxychloride (0.7 ml) and N,N-diethyl aniline (460 μl) and the mixture is heated under reflux for 5.5 hours. The reaction solution is evaporated azeotropically with toluene three times, and to the residue are added aqueous citric acid solution and chloroform, and the mixture is separated. The organic layer is washed with a saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=19:1→17:3) to give 4-chloro-5-methoxy-2-methylsulfanyl-pyrimidine (260 mg). MS (m/z): 191/193 [M+H]+

Aufarbeitung

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 5.5 hours
  3. customThe reaction solution is evaporated azeotropically with toluene three times
  4. additionto the residue are added aqueous citric acid solution and chloroform
  5. customthe mixture is separated
  6. washThe organic layer is washed with a saturated brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=19:1→17:3)

Quellen und Nachweise

ORD-Eintrag
ord-277f5048c1074e8584a00adab101b807
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08076364B2

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