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

HRID 976267Notes

Reaction equation

HRID 976267 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][CH2:35][CH3:36])[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][CH2:35][CH3:36])[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 540600333-Dimethylamino-1-(3-ethoxy-phenyl)-2-propen-1-oneHCID 1785125183-(1,1,2,2-Tetrafluoroethoxy)phenylguanidine nitrate

Product 1

HCID 19967035N-[3-(1,1,2,2-tetrafluoro-ethoxy)-phenyl]-4-(3-ethoxy-phenyl)-2-pyrimidineamine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

926.1 mg (3.69 mmol) of 3-(1,1,2,2-tetrafluoro-ethoxy)-phenyl-guanidine nitrate are added to a solution of 801.1 mg (3.69 mmol) of 3-dimethylamino-1-(3-ethoxy-phenyl)-2-propen-1-one in 10 ml of 2-propanol. After the addition of 162.2 mg (4.05 mmol) of sodium hydroxide, the reaction mixture is boiled under reflux for 20 h. After cooling to RT, the reaction product is isolated by filtration and washed with 1-propanol, ethyl acetate and water. After chromatography (hexane:ethyl acetate=7:3), N-[3-(1,1,2,2-tetrafluoro-ethoxy)-phenyl]-4-(3-ethoxy-phenyl)-2-pyrimidineamine is obtained; Rf =0.72 (methylene chloride:methanol=98:2), m.p. 88°-96°.

Workup

  1. temperatureunder reflux for 20 h
  2. customthe reaction product is isolated by filtration
  3. washwashed with 1-propanol, ethyl acetate and water

Sources & evidence

ORD record
ord-8a949c1679be4ab2ae510ee7a3db2114
Source dataset
uspto-grants-1997_03
Patent number
US05612340

Reaction notes

Loading…