Hydrochloric Acid → Benzonitrile,2-(5-pyrimidinylamino)-

HRID 1735748Notes

Reaction equation

HRID 1735748 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][CH:20]=[CH:19][C:16]=1[C:17]#[N:18].Cl>O.CS(C)=O>[C:17]([C:16]1[CH:19]=[CH:20][CH:21]=[CH:22][C:15]=1[NH:7][C:8]1[CH:9]=[N:10][CH:11]=[N:12][CH:13]=1)#[N:18]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 678552-FluorobenzonitrileHCID 344373Pyrimidin-5-amineHCID 23665647Potassium tert-butoxide

Product 1

HCID 19434388Benzonitrile,2-(5-pyrimidinylamino)-Yield 54%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×

Procedure

To 10 ml of dimethyl sulfoxide was added 1.40 g (12.5 mmol) of potassium tert-butoxide, and to the solution was added 951 mg (10.0 mmol) of 5-aminopyrimidine while cooling with water. After stirring at room temperature for 1 hour, 0.54 ml (5.0 mmol) of 2-fluorobenzonitrile was added thereto while cooling with water, and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was poured into ice-water, and the mixture was adjusted to pH 7.0 with 1 N hydrochloric acid, and filtered. The filter residue was dissolved in 200 ml of acetone, and the acetone solution was filtered. The filtrate was dried over magnesium sulfate, and the solvent was removed by distillation under reduced pressure to obtain 0.53 g (2.70 mmol) of 5-[N-(2cyanophenyl)amino]pyrimidine.

Workup

  1. stirringthe mixture was stirred at room temperature for 30 minutes
  2. filtrationfiltered
  3. dissolutionThe filter residue was dissolved in 200 ml of acetone
  4. filtrationthe acetone solution was filtered
  5. dry with materialThe filtrate was dried over magnesium sulfate
  6. customthe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-a4b6c11e1a6e4a48af9161ced78c9c90
Source dataset
uspto-grants-1996_07
Patent number
US05538976

Reaction notes

Loading…