Sodium Hydroxide → N-(3-trifluoromethyl-phenyl)-4-pyridyl-2-pyrimidineamine

HRID 724818

Reaction equation

HRID 724818 reaction equation
[N+]([O-])(O)=O.[F:5][C:6]([F:18])([F:17])[C:7]1[CH:8]=[C:9]([NH:13][C:14]([NH2:16])=[NH:15])[CH:10]=[CH:11][CH:12]=1.[OH-].[Na+].CN(C)[CH:23]=[CH:24][C:25]([C:27]1[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=1)=O>C(O)(C)C>[F:5][C:6]([F:17])([F:18])[C:7]1[CH:8]=[C:9]([NH:13][C:14]2[N:16]=[C:25]([C:27]3[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=3)[CH:24]=[CH:23][N:15]=2)[CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 7145312-Propen-1-one, 3-(dimethylamino)-1-(4-pyridinyl)-HCID 178418402HCID 178418402, compound

Product 1

HCID 14347000N-(3-trifluoromethyl-phenyl)-4-pyridyl-2-pyrimidineamine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

15.1 g (0.0567 mmol) of 3-trifluoromethyl-phenyl-guanidine nitrate and 2.84 g (70.9 mmol) of sodium hydroxide are added to a suspension of 10 g (56.7 mmol) of 3-dimethylamino-1-(4-pyridyl)-2-propen-1-one [described in EP-A-0 233 461] in 300 ml of isopropanol The reaction mixture is boiled under reflux for 24 hours. After cooling, the product is isolated by filtration, washed with water and dried at 60° under HV. N-(3-trifluoromethyl-phenyl)-4-pyridyl-2-pyrimidineamine is obtained; m.p. 197°-198°, Rf =0.58 (ethyl acetate).

Workup

  1. temperatureunder reflux for 24 hours
  2. temperatureAfter cooling
  3. customthe product is isolated by filtration
  4. washwashed with water
  5. customdried at 60° under HV

Sources & evidence

ORD record
ord-4bdc43d7dd514ddfb08315bfc058db27
Source dataset
uspto-grants-1998_01
Patent number
US05705502

Linked notes

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