Dimethylcarbamoyl Chloride → 4-{2-[(3-Chlorophenyl)amino]pyrimidin-4-yl}pyridine-2-carbonitrile

HRID 724821Notes

Reaction equation

HRID 724821 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[N:14]=[C:13]([C:15]3[CH:20]=[CH:19][N+:18]([O-])=[CH:17][CH:16]=3)[CH:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:22][N:23](C)C(Cl)=O.C[Si](C#N)(C)C>C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[N:14]=[C:13]([C:15]3[CH:20]=[CH:19][N:18]=[C:17]([C:22]#[N:23])[CH:16]=3)[CH:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 82115Trimethylsilyl cyanideHCID 19689585N-(3-chloro-phenyl)-4-(N-oxido4-pyridyl)-2-pyrimidineamine

Product 1

HCID 196896104-{2-[(3-Chlorophenyl)amino]pyrimidin-4-yl}pyridine-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

500 mg (1.67 mmol) of N-(3-chloro-phenyl)-4-(N-oxido-4-pyridyl)-2-pyrimidineamine are suspended in 5 ml of acetonitrile, and 0.42 ml (4.5 mmol) of dimethylcarbamoyl chloride and 0.56 ml (4.5 mmol) of trimethylsilyl cyanide are added. After stirring for 14 hours at 60°, the reaction mixture is cooled to RT and the reaction product is isolated by filtration and washed with diethyl ether. Recrystallisation from tetrahydrofuran gives N-(3-chloro-phenyl)-4-(2-cyano-4-pyridyl)-2-pyrimidineamine in the form of yellow crystals; m.p. 221°-222°, Rf =0.6 (hexane:ethyl acetate=1:1).

Workup

  1. customthe reaction product is isolated by filtration
  2. washwashed with diethyl ether
  3. customRecrystallisation from tetrahydrofuran

Sources & evidence

ORD record
ord-0295c05a68b143898796a6e026e0567c
Source dataset
uspto-grants-1998_01
Patent number
US05705502

Reaction notes

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