Uracil → 1-Benzyloxycarbonylmethyl-2,4-dioxopyrimidine

HRID 2308182

Reaktionsgleichung

Reaktionsgleichung von HRID 2308182
CN(C)C=O.[O:6]=[C:7]1[NH:12][C:11](=[O:13])[CH:10]=[CH:9][NH:8]1.Br[CH2:15][C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17].C(=O)([O-])[O-].[K+].[K+]>O>[CH2:19]([O:18][C:16]([CH2:15][N:8]1[CH:9]=[CH:10][C:11](=[O:13])[NH:12][C:7]1=[O:6])=[O:17])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Komponenten

6

Edukt 4

HCID 1174UracilHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 62576Benzyl bromoacetate

Produkt 1

HCID 226011191-Benzyloxycarbonylmethyl-2,4-dioxopyrimidineAusbeute 60,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To anhydrous dimethylformamide solution (10 ml) containing 2,4-dioxopyrimidine (1.0 g) are added benzyl bromoacetate (2.5 g) and potassium carbonate (2.5 g), and the mixture is stirred at room temperature for 15 hours. The reaction solution is poured into water, and the mixture is extracted with ethyl acetate. The extract is washed with a saturated brine, and dried over anhydrous magnesium sulfate. The solvent is removed by evaporation under reduced pressure, and the precipitated crystals are washed with diethyl ether to give the desired 1-benzyloxycarbonylmethyl-2,4-dioxopyrimidine (1.4 g) as colorless crystals.

Aufarbeitung

  1. extractionthe mixture is extracted with ethyl acetate
  2. washThe extract is washed with a saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent is removed by evaporation under reduced pressure
  5. washthe precipitated crystals are washed with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-ddd691a8b02340e7a32db9bdb3211bb4
Quelldatensatz
uspto-grants-2004_12
Patentnummer
US06835714B1

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