Dimethyl Sulfate → 3-Bromo-6-methoxypyridin-2-amine

HRID 2120757Notes

Reaction equation

HRID 2120757 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[Br:9].[OH-].[K+].[CH3:12]OS(OC)(=O)=O>CC(C)=O>[Br:9][C:3]1[C:2]([NH2:1])=[N:7][C:6]([O:8][CH3:12])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 14797Potassium HydroxideHCID 178508959HCID 178508959, compound

Product 1

HCID 234358793-Bromo-6-methoxypyridin-2-amineYield 28%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A suspension of 11.58 g (61 mmol) 6-amino-5-bromo-pyridin-2-ol in 200 ml acetone was treated with 10.3 g (184 mmol) KOH pellets and 10 g (80 mmol) dimethylsulfate. The mixture was stirred for 4 h at room temperature and evaporated to dryness. 400 ml water was added and the mixture was extracted four times with 300 ml ethyl acetate. The combined organic phases were dried with MgSO4 and evaporated. The residue was purified by flash column chromatography on silica eluting with hexane/ ethyl acetate 1:1 to yield 3.455 g (28%) of the title compound as orange oil.

Workup

  1. customevaporated to dryness
  2. addition400 ml water was added
  3. extractionthe mixture was extracted four times with 300 ml ethyl acetate
  4. dry with materialThe combined organic phases were dried with MgSO4
  5. customevaporated
  6. customThe residue was purified by flash column chromatography on silica eluting with hexane/ ethyl acetate 1:1

Sources & evidence

ORD record
ord-2fb6a8ffca4242d58494c35052972651
Source dataset
uspto-grants-2004_02
Patent number
US06693116B2

Reaction notes

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