Dimethylcarbamoyl Chloride → N-(3-trifluoromethyl-phenyl)-4-(2-cyano-4-pyridyl)-2-pyrimidineamine

HRID 724817Notes

Reaction equation

HRID 724817 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:4]=[C:5]([NH:9][C:10]2[N:15]=[C:14]([C:16]3[CH:21]=[CH:20][N+:19]([O-])=[CH:18][CH:17]=3)[CH:13]=[CH:12][N:11]=2)[CH:6]=[CH:7][CH:8]=1.C[Si]([C:29]#[N:30])(C)C.CN(C)C(Cl)=O>C(#N)C>[F:1][C:2]([F:24])([F:23])[C:3]1[CH:4]=[C:5]([NH:9][C:10]2[N:15]=[C:14]([C:16]3[CH:21]=[CH:20][N:19]=[C:18]([C:29]#[N:30])[CH:17]=3)[CH:13]=[CH:12][N:11]=2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 82115Trimethylsilyl cyanideHCID 105926524-[2-[[3-(Trifluoromethyl)phenyl]amino]pyrimidin-4-yl]pyridine 1-oxide

Product 1

HCID 19711150N-(3-trifluoromethyl-phenyl)-4-(2-cyano-4-pyridyl)-2-pyrimidineamine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

0.8 g (2.41 mmol) of N-(3-trifluoromethyl-phenyl)-4-(N-oxido4-pyridyl)-2-pyrimidineamine is suspended in 40 ml of acetonitrile. 0.834 ml (6.65 mmol) of tri-methylsilyl cyanide and 0.611 ml (6.665 mmol) of dimethylcarbamoyl chloride are added and the reaction mixture is stirred for 12 hours at 60°. After concentration under reduced pressure, crystallisation is effected from tetrahydrofuran/diethyl ether. N-(3-trifluoromethyl-phenyl)-4-(2-cyano-4-pyridyl)-2-pyrimidineamine is obtained; m.p. 164°-166°, Rf =0.40 (n-hexane:ethyl acetate=1:1).

Workup

  1. concentrationAfter concentration
  2. customunder reduced pressure, crystallisation

Sources & evidence

ORD record
ord-43ed1896744740fbbcd551bcc51b7f8e
Source dataset
uspto-grants-1998_01
Patent number
US05705502

Reaction notes

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