Water → 1-Benzyl-5-bromo-1,2,3,4-tetrahydropyrimidine-2,4-dione

HRID 1977234Notes

Reaction equation

HRID 1977234 reaction equation
[Br:1][C:2]1[C:3](=[O:9])[NH:4][C:5](=[O:8])[NH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O>CN(C)C=O>[CH2:16]([N:6]1[CH:7]=[C:2]([Br:1])[C:3](=[O:9])[NH:4][C:5]1=[O:8])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 58025-BromouracilHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 5-bromouracil (5.0 g, 26 mmol) and potassium carbonate (7.2 g, 52 mmol) in N,N-dimethylformamide (25 mL) was added benzyl bromide (3.1 mL, 26 mmol) and the reaction mixture stirred 72 h. The reaction was treated with water (50 mL) and then extracted into ethyl acetate (3×75 mL). The aqueous layer was further extracted with dichloromethane (3×100 mL), the dichloromethane layers were combined, washed with water (2×50 mL), brine (1×50 mL), dried over magnesium sulfate, filtered and concentrated in vacuo. The resulting mixture of products was purified by pressurized silica gel chromatography (25% ethyl acetate in hexane) to provide 1-benzyl-5-bromo-1H-pyrimidine-2,4-dione.

Workup

  1. extractionextracted into ethyl acetate (3×75 mL)
  2. extractionThe aqueous layer was further extracted with dichloromethane (3×100 mL)
  3. washwashed with water (2×50 mL), brine (1×50 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. additionThe resulting mixture of products
  8. customwas purified by pressurized silica gel chromatography (25% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-64473c567bd74c09b44d694d7fd48f7d
Source dataset
uspto-grants-2001_05
Patent number
US06232318B1

Reaction notes

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