Sodium Hydroxide → N-[3-(1,1,2,2-tetrafluoro-ethoxy)-phenyl]-4-(3,4,5-trimethoxyphenyl)-2-pyrimidineamine

HRID 976261Notes

Reaction equation

HRID 976261 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]=[C:32]([O:34][CH3:35])[C:31]([O:36][CH3:37])=[C:30]([O:38][CH3:39])[CH:29]=1)=O.[OH-].[Na+]>C(O)CC>[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:29]=[C:30]([O:38][CH3:39])[C:31]([O:36][CH3:37])=[C:32]([O:34][CH3:35])[CH:33]=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 539569023-(Dimethylamino)-1-(3,4,5-trimethoxyphenyl)prop-2-EN-1-oneHCID 1785125183-(1,1,2,2-Tetrafluoroethoxy)phenylguanidine nitrate

Product 1

HCID 19966971N-[3-(1,1,2,2-tetrafluoro-ethoxy)-phenyl]-4-(3,4,5-trimethoxyphenyl)-2-pyrimidineamine

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

1189.4 mg (0.75 mmol) of 3-(1,1,2,2-tetrafluoro-ethoxy)-phenyl-guanidine nitrate are added to a solution of 200 mg (0.75 mmol) of 3-dimethylamino-1-(3,4,5-trimethoxy-phenyl)-2-propen-1-one in 11.5 ml of 1-propanol. After the addition of 33.2 mg (0.83 mmol) of sodium hydroxide, the reaction mixture is boiled under reflux for 23 hours. After cooling to RT, the reaction product is isolated by filtration and washed with 1-propanol and water. After drying at 60° C. under HV, N-[3-(1,1,2,2-tetrafluoro-ethoxy)-phenyl]-4-(3,4,5-trimethoxyphenyl)-2-pyrimidineamine is obtained; Rf =0.75 (methylene chloride:methanol=9:1), FAB-MS: 454 (M+ +1), m.p. 132° C.

Workup

  1. temperatureunder reflux for 23 hours
  2. customthe reaction product is isolated by filtration
  3. washwashed with 1-propanol and water
  4. customAfter drying at 60° C. under HV

Sources & evidence

ORD record
ord-0ff0197f2f604f8d969bfc55178f84ff
Source dataset
uspto-grants-1997_03
Patent number
US05612340

Reaction notes

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