Water → 3-Benzoyl-1-(3,3-dimethoxy-propyl)-5-iodo-1H-pyrimidine-2,4-dione

HRID 1925014Notes

Reaction equation

HRID 1925014 reaction equation
[C:1]([N:9]1[C:14](=[O:15])[C:13]([I:16])=[CH:12][NH:11][C:10]1=[O:17])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:25][CH2:26][CH:27]([O:30][CH3:31])[O:28][CH3:29].O>CN(C=O)C>[C:1]([N:9]1[C:14](=[O:15])[C:13]([I:16])=[CH:12][N:11]([CH2:25][CH2:26][CH:27]([O:30][CH3:31])[O:28][CH3:29])[C:10]1=[O:17])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 1189323-Bromopropionaldehyde dimethylacetalHCID 111636643-Benzoyl-5-iodo-1H-pyrimidine-2,4-dione

Product 1

HCID 593375803-Benzoyl-1-(3,3-dimethoxy-propyl)-5-iodo-1H-pyrimidine-2,4-dioneYield 91.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Benzoyl-5-iodo-1H-pyrimidine-2,4-dione (Prep 6, 2.1 g, 6.13 mmol), K2CO3 (846 mg, 6.13 mmol) and 3-bromo-1,1dimethoxy-propane (1 mL, 7.4 mmol) were dissolved in dry DMF under Nitrogen (8 mL). After stirring the reaction at room temperature for 48 h, water was added and the product extracted with diethylether. The organic phase was dried (Na2SO4) and evaporated. The crude was purified by flash chromatography with ethyl acetate-petroleum ether (35-65) to give 2.5 g of the title compound.

Workup

  1. customthe reaction at room temperature for 48 h
  2. extractionthe product extracted with diethylether
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. customevaporated
  5. customThe crude was purified by flash chromatography with ethyl acetate-petroleum ether (35-65)

Sources & evidence

ORD record
ord-e29df940651e49c58a797dc3490ac1ee
Source dataset
uspto-grants-2012_05
Patent number
US08178549B2

Reaction notes

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