[2-(3,5-Dimethyl-pyrazol-1-yl)-9-methyl-9H-purin-6-yl]-(4-nitro-phenyl)-amine → N-[2-(3,5-dimethyl-pyrazol-1-yl)-9-methyl-9H-purin-6-yl]-benzene-1,4-diamine

HRID 1809273Notes

Reaction equation

HRID 1809273 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([CH3:7])[N:4]([C:8]2[N:16]=[C:15]3[C:11]([N:12]=[CH:13][N:14]3[CH3:17])=[C:10]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([N+:25]([O-])=O)=[CH:21][CH:20]=3)[N:9]=2)[N:3]=1>CO.ClCCl.[Pd]>[CH3:1][C:2]1[CH:6]=[C:5]([CH3:7])[N:4]([C:8]2[N:16]=[C:15]3[C:11]([N:12]=[CH:13][N:14]3[CH3:17])=[C:10]([NH:18][C:19]3[CH:20]=[CH:21][C:22]([NH2:25])=[CH:23][CH:24]=3)[N:9]=2)[N:3]=1

Participants

5

Reactant 1

HCID 25016608[2-(3,5-Dimethyl-pyrazol-1-yl)-9-methyl-9H-purin-6-yl]-(4-nitro-phenyl)-amine

Product 1

HCID 25017122N-[2-(3,5-dimethyl-pyrazol-1-yl)-9-methyl-9H-purin-6-yl]-benzene-1,4-diamineYield 98.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

[2-(3,5-Dimethyl-pyrazol-1-yl)-9-methyl-9H-purin-6-yl]-(4-nitro-phenyl)-amine (2.89 g, 7.93 mmol) was dissolved in methanol (50 mL) and dichloromethane (50 mL). Palladium on carbon (5%, 600 mg) was added and the reaction mixture was stirred under a hydrogen atmosphere for 24 hours. Filtration through celite followed by concentration in vacuo gave N-[2-(3,5-dimethyl-pyrazol-1-yl)-9-methyl-9H-purin-6-yl]-benzene-1,4-diamine (2.6 g, 98%) as a yellow foam.

Workup

  1. filtrationFiltration through celite
  2. concentrationfollowed by concentration in vacuo

Sources & evidence

ORD record
ord-e2fcce8a313c40b397d898ca513648e8
Source dataset
uspto-grants-2013_01
Patent number
US08362024B2

Reaction notes

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