Benzene → 2-Amino-5-chloro-3-fluoro-6-(p-methoxybenzylamino)pyridine

HRID 610265Notes

Reaction equation

HRID 610265 reaction equation
CN1CCCC1=O.[NH2:8][C:9]1[C:14]([F:15])=[CH:13][C:12]([Cl:16])=[C:11](F)[N:10]=1.[CH3:18][O:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][NH2:25])=[CH:22][CH:21]=1.C1C=CC=CC=1>CCCCCC>[NH2:8][C:9]1[C:14]([F:15])=[CH:13][C:12]([Cl:16])=[C:11]([NH:25][CH2:24][C:23]2[CH:26]=[CH:27][C:20]([O:19][CH3:18])=[CH:21][CH:22]=2)[N:10]=1

Participants

6

Reactant 4

HCID 241BenzeneHCID 13387N-methyl-2-pyrrolidoneHCID 754524-MethoxybenzylamineHCID 221212475-Chloro-3,6-difluoropyridin-2-amine

Product 1

HCID 221212532-Amino-5-chloro-3-fluoro-6-(p-methoxybenzylamino)pyridineYield 109.9%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
150 °C

Procedure

To 2 ml of N-methylpyrrolidone was added 510 mg of 2-amino-5-chloro-3,6-difluoropyridine and 910 mg of p-methoxybenzylamine, and the mixture was stirred at 150° C. for one day, and allowed to cool. After adding a mixed solution of 60 ml benzene and n-hexane (1:1, v/v), the solution was washed twice with 400 ml of distilled water. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain 960 mg of the title compound as a brown crude oil.

Workup

  1. temperatureto cool
  2. washv/v), the solution was washed twice with 400 ml of distilled water
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-98355be94d834f8d92173720a1fa5c32
Source dataset
uspto-grants-1999_12
Patent number
US05998436

Reaction notes

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