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

HRID 12673Notes

Reaction equation

HRID 12673 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[CH:25]([Cl:28])[CH2:26][CH3:27].O>CN(C=O)C>[C:1]([N:9]1[C:14](=[O:15])[C:13]([I:16])=[CH:12][N:11]([CH2:27][CH2:26][CH2:25][Cl:28])[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 36872Propane, bromochloro-HCID 111636643-Benzoyl-5-iodo-1H-pyrimidine-2,4-dione

Product 1

HCID 593375923-Benzoyl-1-(3-chloro-propyl)-5-iodo-1H-pyrimidine-2,4-dioneYield 98.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Benzoyl-5-iodo-1H-pyrimidine-2,4-dione (Prep36, 3 g, 8.77 mmol) and K2CO3 (1.2 g, 8.77 mmol) were suspended in dry DMF (45 mL) and stirred at room temperature for 1 h. Then, bromo-chloro-propane (2.7 mL, 17.5 mmol) was added dropwise and the mixture stirred at room temperature overnight. Water was added and the mixture was extracted with ethyl acetate. The organic phase was dried (Na2SO4), filtered and evaporated to give the title compound as a pale yellow oil (3.6 g, 98% yield).

Workup

  1. stirringthe mixture stirred at room temperature overnight
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-e06524fe40ad4c5a873fc85d108fc91f
Source dataset
uspto-grants-2010_06
Patent number
US07727988B2

Reaction notes

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