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

HRID 610288
Notes
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Reaction equation

HRID 610288 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 23938Palladium
Catalyst
HCID 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-42bb23c7466343749ac499739f592c04
Source dataset
uspto-grants-1999_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05998436

Reaction notes

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