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

HRID 12670Notes

Reaction equation

HRID 12670 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 36, 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 (91% yield).

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-dbe5faee50cd40d8b78bce49cf576f06
Source dataset
uspto-grants-2010_06
Patent number
US07727988B2

Reaction notes

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