Bromine → 1-Benzyluracil

HRID 1783597

Reaction equation

HRID 1783597 reaction equation
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

Participants

5

Reactant 2

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

Product 1

HCID 2379621-Benzyluracil

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-2279370aa0c2485cbfa231929bf5bf2b
Source dataset
uspto-grants-2009_03
Patent number
US07501429B2

Linked notes

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