Sodium Hydroxide → [4-(4-Chloro-phenyl)-pyrimidin-2-yl]-[3-(1,1,2,2-tetrafluoro-ethoxy)-phenyl]-amine

HRID 976265Notes

Reaction equation

HRID 976265 reaction equation
[N+]([O-])(O)=O.[F:5][C:6]([F:21])([O:10][C:11]1[CH:12]=[C:13]([NH:17][C:18]([NH2:20])=[NH:19])[CH:14]=[CH:15][CH:16]=1)[CH:7]([F:9])[F:8].CN(C)[CH:24]=[CH:25][C:26]([C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=1)=O.[OH-].[Na+]>CC(O)C>[F:5][C:6]([F:21])([O:10][C:11]1[CH:12]=[C:13]([NH:17][C:18]2[N:20]=[C:26]([C:28]3[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=3)[CH:25]=[CH:24][N:19]=2)[CH:14]=[CH:15][CH:16]=1)[CH:7]([F:8])[F:9]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 605938(2E)-1-(4-chlorophenyl)-3-(dimethylamino)prop-2-en-1-oneHCID 1785125183-(1,1,2,2-Tetrafluoroethoxy)phenylguanidine nitrate

Product 1

HCID 19966997[4-(4-Chloro-phenyl)-pyrimidin-2-yl]-[3-(1,1,2,2-tetrafluoro-ethoxy)-phenyl]-amine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

539 mg (2.15 mmol) of 3-(1,1,2,2-tetrafluoro-ethoxy)-phenyl-guanidine nitrate are added to a solution of 450 mg (2.15 mmol) of 3-dimethylamino-1-(4-chloro-phenyl)-2-propen-1-one in 5.5 ml of 2-propanol. After the addition of 94.5 mg (2.36 mmol) of sodium hydroxide, the reaction mixture is boiled under reflux for 29 h. After cooling to RT, the product is isolated by filtration and washed with 1-propanol and water. After drying at 60° under HV, N-[3-(1,1,2,2-tetrafluoro-ethoxy)-phenyl]-4-(4-chloro-phenyl)-2-pyrimidineamine is obtained; Rf =0.45 (methylene chloride:methanol =98:2), MS: 397 (M+), m.p. 133°-135°.

Workup

  1. temperatureunder reflux for 29 h
  2. customthe product is isolated by filtration
  3. washwashed with 1-propanol and water
  4. customAfter drying at 60° under HV

Sources & evidence

ORD record
ord-32387682b29b476d94088b49d2225dd9
Source dataset
uspto-grants-1997_03
Patent number
US05612340

Reaction notes

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