Benzylamine → 2-Benzylamino-4-amino-5-fluoropyridine

HRID 1274726Notes

Reaction equation

HRID 1274726 reaction equation
CN1CCCC1=O.[NH2:8][C:9]1[C:14]([F:15])=[CH:13][N:12]=[C:11](F)[CH:10]=1.[CH2:17]([NH2:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(Cl)(Cl)Cl>[CH2:17]([NH:24][C:11]1[CH:10]=[C:9]([NH2:8])[C:14]([F:15])=[CH:13][N:12]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 13387N-methyl-2-pyrrolidoneHCID 221211752,5-Difluoropyridin-4-amine

Product 1

HCID 221212872-Benzylamino-4-amino-5-fluoropyridineYield 58.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 1 ml of N-methylpyrrolidone was added 410 mg of 4-amino-2,5-difluoropyridine together with 930 mg of benzylamine, and the mixture was allowed to react in nitrogen atmosphere at 150° C. for 3 days and allowed to cool. After adding 30 ml of chloroform, the mixture was washed twice with 300 ml of distilled water. The chloroform layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was subjected to column chromatography (silica gel, 15 g; eluent: chloroform: methanol, 1:0 and then, 50:1) to obtain 400 mg of the title compound as a colorless solid.

Workup

  1. customto react in nitrogen atmosphere at 150° C. for 3 days
  2. temperatureto cool
  3. washthe mixture was washed twice with 300 ml of distilled water
  4. dry with materialThe chloroform layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-eb5a36300cc0482bb95952b3a457533b
Source dataset
uspto-grants-2000_12
Patent number
US06156903

Reaction notes

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