Water → 5-Bromo-2-chloro-4-(4-methoxyphenoxy)pyrimidine

HRID 480017Notes

Reaction equation

HRID 480017 reaction equation
[Br:1][C:2]1[C:3](Cl)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[Br:1][C:2]1[C:3]([O:18][C:15]2[CH:16]=[CH:17][C:12]([O:11][CH3:10])=[CH:13][CH:14]=2)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 90154-MethoxyphenolHCID 11430Potassium CarbonateHCID 2899735-Bromo-2,4-dichloropyrimidine

Product 1

HCID 729424805-Bromo-2-chloro-4-(4-methoxyphenoxy)pyrimidineYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-bromo-2,4-dichloropyrimidine (5.0 g, 22.0 mmol), 4-methoxyphenol (2.72 g, 22.0 mmol) and potassium carbonate (6.07 g, 44.0 mmol) in DMF (20 ml) was stirred for 24 hours. The mixture was added to water (100 ml) and the solid which separated out was collected by filtration, washed with water (50 ml) and dried under high vacuum to give the product (6.6 g, 96%). NMR: 3.8 (s, 3H), 7.0 (d, 2H), 7.2 (d, 2H), 8.8 (s, 1H).

Workup

  1. customthe solid which separated out
  2. filtrationwas collected by filtration
  3. washwashed with water (50 ml)
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-3357756ad9d64db9a49bc788695fac13
Source dataset
uspto-grants-2003_11
Patent number
US06649608B2

Reaction notes

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