Cyanide → N-[3-(1,1,2,2-tetrafluoro-ethoxy)phenyl]-4-(2-cyano-4-pyridyl)-2-pyrimidineamine

HRID 976274Notes

Reaction equation

HRID 976274 reaction equation
[F:1][C:2]([F:27])([O:6][C:7]1[CH:8]=[C:9]([NH:13][C:14]2[N:19]=[C:18]([C:20]3[CH:25]=[CH:24][N+:23]([O-])=[CH:22][CH:21]=3)[CH:17]=[CH:16][N:15]=2)[CH:10]=[CH:11][CH:12]=1)[CH:3]([F:5])[F:4].[C-]#N.[CH3:30][N:31](C)C(Cl)=O>C(#N)C>[F:1][C:2]([F:27])([O:6][C:7]1[CH:8]=[C:9]([NH:13][C:14]2[N:19]=[C:18]([C:20]3[CH:25]=[CH:24][N:23]=[C:22]([C:30]#[N:31])[CH:21]=3)[CH:17]=[CH:16][N:15]=2)[CH:10]=[CH:11][CH:12]=1)[CH:3]([F:5])[F:4]

Participants

5

Reactant 3

HCID 5975CyanideHCID 6598Dimethylcarbamoyl ChlorideHCID 19966995N-[3-(1,1,2,2-tetrafluoroethoxy)phenyl]-4-(N-oxido-4-pyridyl)-2-pyrimidine-amine

Product 1

HCID 19967016N-[3-(1,1,2,2-tetrafluoro-ethoxy)phenyl]-4-(2-cyano-4-pyridyl)-2-pyrimidineamine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

100 mg (0.26 mmol) of N-[3-(1,1,2,2-tetrafluoro-ethoxy)-phenyl]-4-(N-oxido-4-pyridyl)-2-pyrimidineamine, 90 μl (0.72 mmol) or trimethylsiyl cyanide and 66 μl (0.72 mmol of N,N-dimethyl-carbamoyl chloride are dissolved in 5 ml of acetonitrile and stirred at 60° for 14 h. Concentration under reduced pressure and recrystalisation from tetrahydrofuran/diethyl ether give N-[3-(1,1,2,2-tetrafluoro-ethoxy)phenyl]-4-(2-cyano-4-pyridyl)-2-pyrimidineamine; FAB-MS: 390 (M+ +H), Rf =0.7 (hexane:ethyl acetate=1:1).

Workup

  1. concentrationConcentration
  2. customunder reduced pressure and recrystalisation from tetrahydrofuran/diethyl ether

Sources & evidence

ORD record
ord-8c9fbd90faf345cea12acfd92c9da82c
Source dataset
uspto-grants-1997_03
Patent number
US05612340

Reaction notes

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