Water → 5-Bromo-2-chloro-4-methoxypyrimidine

HRID 2357658Notes

Reaction equation

HRID 2357658 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].[Na+].O>CO>[Br:1][C:2]1[C:3]([O:11][CH3:10])=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2899735-Bromo-2,4-dichloropyrimidineHCID 10942334Sodium Methoxide

Product 1

HCID 36631435-Bromo-2-chloro-4-methoxypyrimidineYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of 5-bromo-2,4-dichloropyrimidine (1.000 mL, 7.82 mmol) in MeOH at 0° C. was added sodium methoxide (1.45 mL, 7.82 mmol). The reaction was warmed up to 23° C. and allowed to stir overnight. Water was added and the mixture was extracted with dichloromethane. The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated to give 1.73 g of 5-bromo-2-chloro-4-methoxypyrimidine as a white solid. ES+=224.9 (M+H)

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a3ea769e62ea483f99ac518a3636c45d
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

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