Sodium Hydroxide → N-[3-(1,1,2,2-tetrafluoro-ethoxy)-phenyl]-4-(3-methoxy-phenyl)-2-pyrimidineamine

HRID 976264Notes

Reaction equation

HRID 976264 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][CH:31]=[C:30]([O:34][CH3:35])[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][CH:31]=[C:30]([O:34][CH3:35])[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 425737963-Dimethylamino-3'-methoxyacrylophenoneHCID 1785125183-(1,1,2,2-Tetrafluoroethoxy)phenylguanidine nitrate

Product 1

HCID 19966972N-[3-(1,1,2,2-tetrafluoro-ethoxy)-phenyl]-4-(3-methoxy-phenyl)-2-pyrimidineamine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

21.28 g (84.7 mmol) of 3-(1,1,2,2-tetrafluoro-ethoxy)-phenyl-guanidine nitrate are added to a solution of 17.4 g (84.7 mmol) of 3-dimethylamino-1-(3-methoxy-phenyl)-2-propen-1-one in 100 ml of 2-propanol. After the addition of 3.72 g (93.2 mmol) of sodium hydroxide, the reaction mixture is boiled under reflux for 21.3 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-(3-methoxy-phenyl)-2-pyrimidineamine is obtained; Rf =0.7 (methylene chloride:methanol =9:1), FAB-MS: 397 (M+ +1), m.p. 103°-104°.

Workup

  1. temperatureunder reflux for 21.3 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-730596eafdc64575863e47958eb70a3c
Source dataset
uspto-grants-1997_03
Patent number
US05612340

Reaction notes

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