Hydrochloric Acid → 4-(Pyrimidin-5-ylamino)benzonitrile

HRID 1735744Notes

Reaction equation

HRID 1735744 reaction equation
CC(C)([O-])C.[K+].[NH2:7][C:8]1[CH:9]=[N:10][CH:11]=[N:12][CH:13]=1.F[C:15]1[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][CH:16]=1.Cl>CS(C)=O>[C:19]([C:18]1[CH:21]=[CH:22][C:15]([NH:7][C:8]2[CH:9]=[N:10][CH:11]=[N:12][CH:13]=2)=[CH:16][CH:17]=1)#[N:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 145174-FluorobenzonitrileHCID 344373Pyrimidin-5-amineHCID 23665647Potassium tert-butoxide

Product 1

HCID 105358714-(Pyrimidin-5-ylamino)benzonitrileYield 53.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To 20 ml of dimethyl sulfoxide was added 2.8 g of potassium tert-butoxide. After stirring at room temperature for 30 minutes, 1.9 g of 5-aminopyrimidine was added thereto, followed by stirring at room temperature for 30 minutes. To the solution was added 1.21 g of 4-fluorobenzonitrile, and the mixture was stirred at room temperature for 30 minutes and then at 50° C. for 30 minutes. The reaction mixture was poured into ice-water, neutralized with hydrochloric acid. The resulting crystals were collected by filtration and dissolved in acetone. Any insoluble matter was removed by filtration, and the solvent was removed by distillation. The resulting crystals were washed with ethyl ether to obtain 1.04 g of 5-[(4-cyanophenyl)amino]pyrimidine.

Workup

  1. stirringby stirring at room temperature for 30 minutes
  2. stirringthe mixture was stirred at room temperature for 30 minutes
  3. waitat 50° C. for 30 minutes
  4. filtrationThe resulting crystals were collected by filtration
  5. dissolutiondissolved in acetone
  6. customAny insoluble matter was removed by filtration
  7. customthe solvent was removed by distillation
  8. washThe resulting crystals were washed with ethyl ether

Sources & evidence

ORD record
ord-05f6da7e9d354254aa130a3a32009bab
Source dataset
uspto-grants-1996_07
Patent number
US05538976

Reaction notes

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