Methanol → 6-Bromo-2-methoxypyridin-3-amine

HRID 1872051Notes

Reaction equation

HRID 1872051 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5](OC)=[N:6]C=1.[CH2:10](Cl)Cl.[CH3:13][OH:14].[Br-:15].[Br-].[Br-].C([N+](C)(C)C)C1C=CC=CC=1.C([N+](C)(C)C)C1C=CC=CC=1.C([N+](C)(C)C)C1C=CC=CC=1>O>[NH2:6][C:5]1[CH:4]=[CH:3][C:2]([Br:15])=[N:1][C:13]=1[O:14][CH3:10]

Participants

6

Reactant 4

HCID 887MethanolHCID 6344DichloromethaneHCID 811216-Methoxy-3-pyridinylamineHCID 53442637Benzyltrimethylammoniumtribromide

Product 1

HCID 105361376-Bromo-2-methoxypyridin-3-amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Part A: To 3.18 grams (25.6 mmol) of commercially available 5-amino-2-methoxypyridine in a solution of methylene chloride (50 ml) and methanol (20 ml) was added benzyltrimethylammonium tribromide (10 g, 25.6 mmol) and the mixture was stirred at room temperature for 24 hours. The solvent was then stripped and the resulting residue was taken up in water and extracted (3×100 mL) with ethyl acetate. The organic extracts were dried with magnesium sulfate, filtered, and concentrated in vacuo. The crude material was chromatographed on silica using 30% ethyl acetate in hexanes as solvent to afford 5-amino-2-bromo-6-methoxypyridine. C6H7N2OBr MS 203 (M+H)+.

Workup

  1. extractionextracted (3×100 mL) with ethyl acetate
  2. dry with materialThe organic extracts were dried with magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude material was chromatographed on silica using 30% ethyl acetate in hexanes as solvent

Sources & evidence

ORD record
ord-e00a2605852b4622bcf829be9abc36f4
Source dataset
uspto-grants-2000_08
Patent number
US06107301

Reaction notes

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