Sodium Acetate → 4-(3,5-Dichlorophenyl)-6-ethyl-2-(methylthio)-1,4-dihydropyrimidine-5-carboxylic acid methylester

HRID 1182577Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1182577
[CH3:1][O:2][C:3](=[O:18])[C:4]([C:14](=O)[CH2:15][CH3:16])=[CH:5][C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]([Cl:13])[CH:7]=1.C[NH:20][C:21](=[NH:23])[SH:22].S([O-])([O-])(=O)=O.[C:29]([O-])(=O)C.[Na+]>CN(C=O)C>[CH3:1][O:2][C:3]([C:4]1[CH:5]([C:6]2[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]([Cl:13])[CH:7]=2)[N:23]=[C:21]([S:22][CH3:29])[NH:20][C:14]=1[CH2:15][CH3:16])=[O:18]

Komponenten

5

Edukt 3

HCID 517045Sodium AcetateHCID 858136683-(3,5-Dichlorophenyl)-2-propionyl-acrylic methylesterHCID 178485224HCID 178485224, Verbindung

Produkt 1

HCID 866191954-(3,5-Dichlorophenyl)-6-ethyl-2-(methylthio)-1,4-dihydropyrimidine-5-carboxylic acid methylester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

1.00 g (3.48 mmol) of 3-(3,5-dichlorophenyl)-2-propionyl-acrylic methylester was dissolved in 10 ml of DMF. 776 mg (2.79 mmol) of methylisothiourea-sulfate and 428 mg (5.22 mmol) of sodium acetate were added at room temperature and stirred at the same temperature for 2 days. After DMF was evaporated under reduced pressure, the reaction mixture was diluted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was dissolved in toluene and catalytic amount of silica gel was added and stirred at 100° C. for one day. After filtering silica gel, the filtrate was concentrated under reduced pressure. The residue was purified by the silica gel chromatography (hexane/ethyl acetate=10/1 to 2/1) to obtain the title compound.

Aufarbeitung

  1. customAfter DMF was evaporated under reduced pressure
  2. additionthe reaction mixture was diluted with ethyl acetate
  3. washThe organic layer was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe residue was dissolved in toluene
  7. additioncatalytic amount of silica gel was added
  8. stirringstirred at 100° C. for one day
  9. filtrationAfter filtering silica gel
  10. concentrationthe filtrate was concentrated under reduced pressure
  11. customThe residue was purified by the silica gel chromatography (hexane/ethyl acetate=10/1 to 2/1)

Quellen und Nachweise

ORD-Eintrag
ord-dc82fdf47fbf42cdb1585e0b7da85c15
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07288544B2

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