4-Methoxyphenol → 5-bromo-2-(4-methoxyphenoxy)pyrimidine

HRID 2295945Notes

Reaction equation

HRID 2295945 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5](Cl)=[N:6][CH:7]=1.[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[Br:1][C:2]1[CH:3]=[N:4][C:5]([O:17][C:14]2[CH:15]=[CH:16][C:11]([O:10][CH3:9])=[CH:12][CH:13]=2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 90154-MethoxyphenolHCID 11430Potassium CarbonateHCID 6066655-Bromo-2-chloropyrimidine

Product 1

HCID 45415135-bromo-2-(4-methoxyphenoxy)pyrimidineYield 78%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

5-Bromo-2-chloropyrimidine (3.0 g), p-methoxyphenol (2.5 g), methyl ethyl ketone (50 ml--dried over anhydrous potassium carbonate) and anhydrous potassium carbonate (2.5 g) were heated under reflux with stirring for 6 hours. The solvent was evaporated under reduced pressure, the residue treated with water and the precipitated compound collected by filtration. The product was treated with 5% sodium hydroxide aqueous solution and the mixture stirred for approximately 30 minutes. The solid was collected by filtration, washed with water and recrystallised from methanol/water to give the title compound (3.4 g), m.p. 92° C.

Workup

  1. temperatureunder reflux
  2. customThe solvent was evaporated under reduced pressure
  3. additionthe residue treated with water
  4. filtrationthe precipitated compound collected by filtration
  5. additionThe product was treated with 5% sodium hydroxide aqueous solution
  6. stirringthe mixture stirred for approximately 30 minutes
  7. filtrationThe solid was collected by filtration
  8. washwashed with water
  9. customrecrystallised from methanol/water

Sources & evidence

ORD record
ord-77378b54001e4b25a45851bbc17a4c6c
Source dataset
uspto-grants-1984_01
Patent number
US04427437

Reaction notes

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