Methanol → 2-Amino-3-fluoro-6-(1,1,3,3-tetramethylbutylamino)pyridine

HRID 368512Notes

Reaction equation

HRID 368512 reaction equation
CO.[NH2:3][C:4]1[C:9]([F:10])=[C:8]([Br:11])[C:7](Cl)=[C:6]([NH:13][C:14]([CH3:21])([CH3:20])[CH2:15][C:16]([CH3:19])([CH3:18])[CH3:17])[N:5]=1>[Pd].C(N(CC)CC)C>[NH2:3][C:4]1[C:9]([F:10])=[CH:8][CH:7]=[C:6]([NH:13][C:14]([CH3:21])([CH3:20])[CH2:15][C:16]([CH3:19])([CH3:18])[CH3:17])[N:5]=1.[NH2:3][C:4]1[C:9]([F:10])=[C:8]([Br:11])[CH:7]=[C:6]([NH:13][C:14]([CH3:21])([CH3:20])[CH2:15][C:16]([CH3:19])([CH3:18])[CH3:17])[N:5]=1

Participants

6

Reactant 2

HCID 887MethanolHCID 221211602-Amino-4-bromo-5-chloro-3-fluoro-6-(1,1,3,3-tetramethylbutylamino)pyridine

Product 2

HCID 177787632-Amino-3-fluoro-6-(1,1,3,3-tetramethylbutylamino)pyridineHCID 221212652-Amino-4-bromo-3-fluoro-6-(1,1,3,3-tetramethylbutylamino)pyridine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8471TriethylamineSolvent

Procedure

To 10 ml of methanol were added 1.6 g of 2-amino-4-bromo-5-chloro-3-fluoro-6-(1,1,3,3-tetramethylbutylamino)pyridine together with 0.47 g of triethylamine and 0.09 g of 10% palladium on carbon, and the mixture was hydrogenated at room temperature for 39 hours. The catalyst was separated by filtration, and the solvent and the like were distilled off under reduced pressure. To the residue was added 50 ml of chloroform, and the mixture was washed with 50 ml of distilled water. The chloroform layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was subjected to chromatography (silica gel, 25 g; eluent: chloroform) to obtain 0.75 g of 2-amino-3-fluoro-6-(1,1,3,3-tetramethylbutylamino)pyridine as a pale brown oil, and 0.2 g of 2-amino-4-bromo-3-fluoro-6-(1,1,3,3-tetramethylbutylamino)pyridine as a brown oil.

Workup

  1. customThe catalyst was separated by filtration
  2. distillationthe solvent and the like were distilled off under reduced pressure
  3. additionTo the residue was added 50 ml of chloroform
  4. washthe mixture was washed with 50 ml of distilled water
  5. dry with materialThe chloroform layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9cf5056e24b144a98f8cc533fa3959e4
Source dataset
uspto-grants-2000_10
Patent number
US06133284

Reaction notes

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