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

HRID 12748

Reaction equation

HRID 12748 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][CH2:27][CH2:28][Cl: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][CH2:27][CH2:28][Cl: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 813641-Bromo-4-chlorobutane2×HCID 111636643-Benzoyl-5-iodo-1H-pyrimidine-2,4-dione

Product 1

HCID 589941523-Benzoyl-1-(4-chloro-butyl)-5-iodo-1H-pyrimidine-2,4-dioneYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Benzoyl-5-iodo-1H-pyrimidine-2,4-dione (Prep128, 2.5 g, 7.3 mmol), K2CO3 (1 g, 7.3 mmol) and 1-bromo-4-chloro-butane (1.26 ml, 10.95 mmol) were suspended in dry DMF (10 ml). After stirring the reaction at room temperature overnight, further 1-bromo-4-chloro-butane (840 μl, 7.3 mmol) was added. Water was added and the mixture was extracted with ethyl ether. The organic phase was dried (Na2SO4), filtered and evaporated; the crude was purified by flash chromatography with petroleum ether-ethyl acetate (7-3) to give the title compound as a white solid (3 g, 98% yield).

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl ether
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customthe crude was purified by flash chromatography with petroleum ether-ethyl acetate (7-3)

Sources & evidence

ORD record
ord-fc016c9b3fec4379b34ff4bf91e99717
Source dataset
uspto-grants-2010_06
Patent number
US07727988B2

Linked notes

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