Sodium Chloride → 1-(2-Bromo-4-nitrophenyl)tetrahydropyrimidin-2(1H)-one

HRID 218528

Reaction equation

HRID 218528 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][NH:3][C:2]1=[O:7].CC(C)([O-])C.[K+].[Br:14][C:15]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[CH:17][C:16]=1F.[Cl-].[Na+]>CS(C)=O.O>[Br:14][C:15]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[CH:17][C:16]=1[N:1]1[CH2:6][CH2:5][CH2:4][NH:3][C:2]1=[O:7]

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 696992-Bromo-1-fluoro-4-nitrobenzeneHCID 746152(1H)-Pyrimidinone, tetrahydro-HCID 23665647Potassium tert-butoxide

Product 1

HCID 595867151-(2-Bromo-4-nitrophenyl)tetrahydropyrimidin-2(1H)-one

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

910 mg (9.09 mmol) of tetrahydropyrimidinone in 39 ml of DMSO are admixed at RT with 1.53 g (13.6 mmol) of potassium tert-butoxide, and the mixture is stirred at room temperature for 30 min. 2.00 g (9.09 mmol) of 2-bromo-1-fluoro-4-nitrobenzene are added and the mixture is stirred at 60° C. After 18 h, it is cooled and added to 600 ml of water and 160 ml of saturated aqueous sodium chloride solution. It is extracted three times with 300 ml each time of ethyl acetate, and the combined organic phases are dried over sodium sulfate. After filtration, the solvents are removed under reduced pressure and the residue is purified by chromatography on silica gel (60:1 dichloromethane/ethanol). This affords 481 mg (17% of theory) of the desired compound.

Workup

  1. stirringthe mixture is stirred at 60° C
  2. waitAfter 18 h
  3. temperatureit is cooled
  4. extractionIt is extracted three times with 300 ml each time of ethyl acetate
  5. dry with materialthe combined organic phases are dried over sodium sulfate
  6. filtrationAfter filtration
  7. customthe solvents are removed under reduced pressure
  8. customthe residue is purified by chromatography on silica gel (60:1 dichloromethane/ethanol)

Sources & evidence

ORD record
ord-9f39347d968c465b9431cc946213fff9
Source dataset
uspto-grants-2012_06
Patent number
US08198267B2

Linked notes

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