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Water → 1-(4-Chlorobutyl)-4-(trifluoromethyl)pyrimidin-2(1H)-one

HRID 1678081
Notes
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Reaction equation

HRID 1678081 reaction equation
[OH:1][C:2]1[N:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][N:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:19][CH2:20][CH2:21][CH2:22][Cl:23].O>CN(C)C=O>[Cl:23][CH2:22][CH2:21][CH2:20][CH2:19][N:3]1[CH:4]=[CH:5][C:6]([C:8]([F:11])([F:9])[F:10])=[N:7][C:2]1=[O:1]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 813641-Bromo-4-chlorobutaneHCID 178517744HCID 178517744, compound

Product 1

HCID 673737351-(4-Chlorobutyl)-4-(trifluoromethyl)pyrimidin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

4.6 g (28.3 mmol) of 2-hydroxy-4-trifluoromethylpyrimidine were stirred in 60 ml of N,N-dimethylformamide (DMF) and 3.9 g (28.3 mmol) of K2CO3 at room temperature for 1 hour. Then 4.9 g (28.3 mmol) of 1-bromo-4-chlorobutane were added dropwise, and the reaction mixture was stirred at room temperature for 6 hours. Water was then added to the reaction mixture, and the aqueous mixture was extracted with diethyl ether. The aqueous phase was made alkaline by adding NaOH, and the aqueous phase was extracted with methylene chloride. The organic phase was then dried, the desiccant was removed by filtration, and the solvent was evaporated to dryness in vacuo; yield: 1.7 g.

Workup

  1. extractionthe aqueous mixture was extracted with diethyl ether
  2. additionby adding NaOH
  3. extractionthe aqueous phase was extracted with methylene chloride
  4. customThe organic phase was then dried
  5. customthe desiccant was removed by filtration
  6. customthe solvent was evaporated to dryness in vacuo

Sources & evidence

ORD record
ord-be156d9ed4784c38bd6c91c61d3abc48
Source dataset
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08008488B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes