3-chloro-4-fluoro-N-(5-nitropyrimidin-2-yl)benzamide → N-(5-aminopyrimidin-2-yl)-3-chloro-4-fluorobenzamide

HRID 750475

Reaction equation

HRID 750475 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1[F:20])[C:5]([NH:7][C:8]1[N:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][N:9]=1)=[O:6].[H][H]>CCO.CO.[Pt]>[NH2:14][C:11]1[CH:12]=[N:13][C:8]([NH:7][C:5](=[O:6])[C:4]2[CH:17]=[CH:18][C:19]([F:20])=[C:2]([Cl:1])[CH:3]=2)=[N:9][CH:10]=1

Participants

6

Reactant 2

HCID 574472633-chloro-4-fluoro-N-(5-nitropyrimidin-2-yl)benzamideHCID 178418361HCID 178418361, compound

Product 1

HCID 21114550N-(5-aminopyrimidin-2-yl)-3-chloro-4-fluorobenzamideYield 80%

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

To 1C (1.16 g, 3.92 mmol) in a mixture of 60 mL EtOH and 10 mL MeOH was added 10% Pt/C (300 mg). The reaction was stirred under 1 atmosphere of hydrogen for 1.5 h, filtered, and concentrated to give 850 mg (80% yield) ID. RP HPLC ret. t.: 1.58 min. and (M+H)+: 267.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. customto give 850 mg (80% yield) ID
  4. custom1.58 min. and (M+H)+

Sources & evidence

ORD record
ord-0452766825dd4b97a1d8aba4b845e575
Source dataset
uspto-grants-2008_07
Patent number
US07405213B2

Linked notes

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