Bromine → 1-Benzyluracil

HRID 1783597

Reaktionsgleichung

Reaktionsgleichung von HRID 1783597
BrBr.[CH2:3]([N:10]1[CH:17]=[C:16](Br)[C:14](=[O:15])[NH:13][C:11]1=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>CS(C)=O.CN(C)C=O>[CH2:3]([N:10]1[CH:17]=[CH:16][C:14](=[O:15])[NH:13][C:11]1=[O:12])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Komponenten

5

Edukt 2

HCID 24408BromineHCID 52766591-Benzyl-5-bromo-1,2,3,4-tetrahydropyrimidine-2,4-dione

Produkt 1

HCID 2379621-Benzyluracil

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittel2×HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

This experiment was performed to verify the role of DMSO solvent in the generation of the bromine electrophile. Thus, this synthesis was done following the same procedure as for the synthesis of 1-benzyl-5-bromouracil, with the sole exception that DMSO was replaced by dimethylformamide (DMF), as solvent. Extraction was done by water-EtOAc and crystallization was done from EtOAc-Hexanes. After filtration, washing with hexanes and drying under high vacuum, 1.4 g of pure 1-benzyluracil, was isolated, as clean white crystals with properties shown below.

Aufarbeitung

  1. extractionExtraction
  2. customwas done by water-EtOAc and crystallization
  3. filtrationAfter filtration
  4. washwashing with hexanes
  5. dry with materialdrying under high vacuum, 1.4 g of pure 1-benzyluracil
  6. customwas isolated, as clean white crystals with properties

Quellen und Nachweise

ORD-Eintrag
ord-2279370aa0c2485cbfa231929bf5bf2b
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07501429B2

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