Methanol → 1-(5-amino-6-methylpyridin-2-yl)-5-methyl-1H-pyrazole-4-carboxylic acid ethyl ester

HRID 1748443Notes

Reaction equation

HRID 1748443 reaction equation
CO.[CH2:3]([O:5][C:6]([C:8]1[CH:9]=[N:10][N:11]([C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[C:16]([CH3:23])[N:15]=2)[C:12]=1[CH3:13])=[O:7])[CH3:4]>[C].[Pd].O1CCOCC1>[CH2:3]([O:5][C:6]([C:8]1[CH:9]=[N:10][N:11]([C:14]2[CH:19]=[CH:18][C:17]([NH2:20])=[C:16]([CH3:23])[N:15]=2)[C:12]=1[CH3:13])=[O:7])[CH3:4]

Participants

5

Reactant 2

HCID 887MethanolHCID 866924135-methyl-1-(6-methyl-5-nitropyridin-2-yl)-1H-pyrazole-4-carboxylic acid ethyl ester

Product 1

HCID 866924121-(5-amino-6-methylpyridin-2-yl)-5-methyl-1H-pyrazole-4-carboxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

Methanol (50 ml), 1,4-dioxane (200 ml) and 10% palladium-carbon (containing ca. 50% water; 5 g) were added to 5-methyl-1-(6-methyl-5-nitropyridin-2-yl)-1H-pyrazole-4-carboxylic acid ethyl ester (15 g) and the mixture was stirred under hydrogen atmosphere at room temperature for four hours. The reaction solution was filtered through Celite, the filtrate was concentrated in vacuo and the resulting solid was washed with n-hexane to give 1-(5-amino-6-methyl-pyridin-2-yl)-5-methyl-1H-pyrazol-4-carboxylic acid ethyl ester as a pale yellow solid.

Workup

  1. filtrationThe reaction solution was filtered through Celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. washthe resulting solid was washed with n-hexane

Sources & evidence

ORD record
ord-097317bb07404a6cb42d6b7b372c5a6d
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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