Water → 3-Benzoyl-5-iodo-1H-pyrimidine-2,4-dione

HRID 12669Notes

Reaction equation

HRID 12669 reaction equation
[I:1][C:2]1[C:3](=[O:9])[NH:4][C:5](=[O:8])[NH:6][CH:7]=1.[C:10](Cl)(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.O>N1C=CC=CC=1>[C:10]([N:4]1[C:3](=[O:9])[C:2]([I:1])=[CH:7][NH:6][C:5]1=[O:8])(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7412Benzoyl chlorideHCID 696725-Iodouracil

Product 1

HCID 111636643-Benzoyl-5-iodo-1H-pyrimidine-2,4-dioneYield 90%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

A solution of 5-iodouracil (commercially available from Aldrich, 2 g, 8.4 mmol) in dry pyridine (20 mL) was added dropwise to a solution of benzoyl chloride (3.5 g, 25.3 mmol) in pyridine (10 mL). The mixture was stirred at room temperature for 3 hours. Water (70 mL) was added and the product extracted with ethyl acetate. The organic phase was washed with a saturated solution of NH4Cl and then with 2% HClaq (40 mL×4 times) The solvent was removed under vacuum and the residue was triturated with i-Pr2O to give the title compound as white solid (2.6 g, 90% yield).

Workup

  1. extractionthe product extracted with ethyl acetate
  2. washThe organic phase was washed with a saturated solution of NH4Cl
  3. customwith 2% HClaq (40 mL×4 times) The solvent was removed under vacuum
  4. customthe residue was triturated with i-Pr2O

Sources & evidence

ORD record
ord-09104cf4b34540c9b46bfd2433b383d8
Source dataset
uspto-grants-2010_06
Patent number
US07727988B2

Reaction notes

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