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

HRID 368487Notes

Reaction equation

HRID 368487 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-f921b1b2a8fc41ecbc2917c6213d7d86
Source dataset
uspto-grants-2000_10
Patent number
US06133284

Reaction notes

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