Uracil → Ethyl (4-hydroxy-2-oxopyrimidin-1(2H)-yl)acetate

HRID 1416402Notes

Reaction equation

HRID 1416402 reaction equation
[NH:1]1[CH:8]=[CH:7][C:5](=[O:6])[NH:4][C:2]1=[O:3].Br[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>O.CS(C)=O>[O:3]=[C:2]1[NH:4][C:5](=[O:6])[CH:7]=[CH:8][N:1]1[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

7

Reactant 4

HCID 1174UracilHCID 5238Sodium IodideHCID 7748Ethyl bromoacetateHCID 11430Potassium Carbonate

Product 1

HCID 293824Ethyl (4-hydroxy-2-oxopyrimidin-1(2H)-yl)acetate

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A dimethyl sulfoxide solution (150 mL) containing 10.02 g of uracil, 3.3 mL of ethyl bromoacetate, 13.85 g of potassium carbonate and 4.52 g of sodium iodide was stirred at 90° C. for six hours. The reaction mixture was poured over water and the mixture was extracted with chloroform. The extracts were combined, dried over sodium sulfate and concentrated in vacuo. The concentrate was poured over a saturated saline solution, the mixture was extracted with ethyl acetate and the extract was dried over sodium sulfate. After concentration, the resulting residue was recrystallized from ethyl acetate to give 2.30 g of ethyl 2,4-dioxo-1,2,3,4-tetrahydropyrimidine-1-acetate.

Workup

  1. extractionthe mixture was extracted with chloroform
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. additionThe concentrate was poured over a saturated saline solution
  5. extractionthe mixture was extracted with ethyl acetate
  6. dry with materialthe extract was dried over sodium sulfate
  7. concentrationAfter concentration
  8. customthe resulting residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-c94bbe17386441bf9047c526e886e22b
Source dataset
uspto-grants-1999_06
Patent number
US05912261

Reaction notes

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