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

HRID 2278430Notes

Reaction equation

HRID 2278430 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 86.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of 5-bromo-2,4-dichloropyrimidine (17.82 g, 78.2 mmol) in methanol (100 mL) stirred at 0° C. was added solid sodium methoxide (4.22 g, 78 mmol) portionwise during 5 minutes. The reaction mixture was stirred at 23° C. overnight. To the organic phase was added water (25 mL) and the methanol was removed. Then it was extracted with dichloromethane. The organic phase was dried over sodium sulphate and evaporated in vacuo to give the title compound as a white solid (17.2 g, 67.6 mmol, 86 yield). LC/MS [M+H]+=223/225.

Workup

  1. customthe methanol was removed
  2. extractionThen it was extracted with dichloromethane
  3. dry with materialThe organic phase was dried over sodium sulphate
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-e4d9e800668b48ba8d7e09e7ffd91b2b
Source dataset
uspto-grants-2015_09
Patent number
US09133178B2

Reaction notes

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