Dimethyl Sulfoxide → 4-chloro-2-fluoro-5-(2-pyrimidinyloxy)aniline

HRID 1953973Notes

Reaction equation

HRID 1953973 reaction equation
[NH2:1][C:2]1[C:3]([F:10])=[CH:4][C:5]([Cl:9])=[C:6]([OH:8])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:18]1[N:23]=[CH:22][CH:21]=[CH:20][N:19]=1.CS(C)=O>CC(=O)CC>[NH2:1][C:2]1[C:3]([F:10])=[CH:4][C:5]([Cl:9])=[C:6]([CH:7]=1)[O:8][C:18]1[N:23]=[CH:22][CH:21]=[CH:20][N:19]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 744042-ChloropyrimidineHCID 1586545-Amino-2-chloro-4-fluorophenol

Product 1

HCID 114478024-chloro-2-fluoro-5-(2-pyrimidinyloxy)anilineYield 75.5%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 5-amino-2-chloro-4-fluorophenol (3.57 g), potassium carbonate (3.04 g), and 2-chloropyrimidine (3.20 g) suspended in butan-2-one (100 ml) and dimethylsulfoxide (10 ml) was heated at reflux overnight. The solution was processed and chromatographed on silica gel eluting with ethyl acetate:hexane, 1:2, to yield yellow crystals (4.0 g). 1H NMR (acetone-d6, TMS): 4.75(2H, br s), 6.78(1H, d, J=8.4 Hz), 7.09(1H, d, J=10.6 Hz), 7.15(1H, t, J=4.8 Hz), 8.56(2H, d, J=4.8 Hz).

Workup

  1. temperatureat reflux overnight
  2. customchromatographed on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-f880b1a4b16645549d8b0c7383a325e4
Source dataset
uspto-grants-2000_09
Patent number
US06121201

Reaction notes

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