Hydrochloric Acid → 2-Amino-6-(t-butylamino)-5-fluoropyridine

HRID 1274712Notes

Reaction equation

HRID 1274712 reaction equation
Cl.C([NH:9][C:10]1[C:15]([Cl:16])=[CH:14][C:13]([F:17])=[C:12]([NH:18][C:19]([CH3:22])([CH3:21])[CH3:20])[N:11]=1)C1C=CC=CC=1>[Pd].CO>[NH2:9][C:10]1[C:15]([Cl:16])=[CH:14][C:13]([F:17])=[C:12]([NH:18][C:19]([CH3:22])([CH3:21])[CH3:20])[N:11]=1.[NH2:9][C:10]1[CH:15]=[CH:14][C:13]([F:17])=[C:12]([NH:18][C:19]([CH3:22])([CH3:21])[CH3:20])[N:11]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 221211832-Benzylamino-6-(t-butylamino)-3-chloro-5-fluoropyridine

Product 2

HCID 221212302-Amino-6-(t-butylamino)-5-fluoropyridineHCID 221212492-Amino-6-(t-butylamino)-3-chloro-5-fluoropyridine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a mixed solution of 18 ml methanol and 1.4 g concentrated hydrochloric acid were added 3.1 g of 2-benzylamino-6-(t-butylamino)-3-chloro-5-fluoropyridine together with 0.33 g of 10% palladium on carbon, and the mixture was hydrogenated at 30° C. for 1 hour. 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 10 ml of 6% aqueous solution of sodium hydroxide, and the chloroform layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was subjected to column chromatography (silica gel, 40 g; eluent: chloroform:n-hexane, 3:1 and then 1:1) to obtain 1.35 g of 2-amino-6-(t-butylamino)-3-chloro-5-fluoropyridine as a pale brown oil, and 0.32 g of 2-amino-6-(t-butylamino)-5-fluoropyridine 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 10 ml of 6% aqueous solution of sodium hydroxide
  5. dry with materialthe chloroform layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6bded959cf714ef8b9f335eca97e240d
Source dataset
uspto-grants-2000_12
Patent number
US06156903

Reaction notes

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