Water → 5-(3-Isobutylureido)-1-methyl-1H-pyrazole-3-carboxylic acid

HRID 541430Notes

Reaction equation

HRID 541430 reaction equation
[CH2:1]([NH:5][C:6](=[O:18])[NH:7][C:8]1[N:12]([CH3:13])[N:11]=[C:10]([C:14]([O:16]C)=[O:15])[CH:9]=1)[CH:2]([CH3:4])[CH3:3].[Li+].[OH-].O>CO>[CH2:1]([NH:5][C:6](=[O:18])[NH:7][C:8]1[N:12]([CH3:13])[N:11]=[C:10]([C:14]([OH:16])=[O:15])[CH:9]=1)[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 68288869Methyl 5-(3-isobutylureido)-1-methyl-1H-pyrazole-3-carboxylate2×

Product 1

HCID 682886485-(3-Isobutylureido)-1-methyl-1H-pyrazole-3-carboxylic acidYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 5-(3-isobutylureido)-1-methyl-1H-pyrazole-3-carboxylate (compound 351.5, 0.12 g, 0.47 mmol) in MeOH (5 ml) was added 1 M LiOH in H2O (1.42 ml, 1.42 mmol). The mixture was stirred at room temperature for 5 hours. TLC showed the reaction was complete. The mixture was acidified to pH 3-4 at 0° C. and then was extracted with EcOAc (2×50 ml). The combined organic layers were dried with Na2SO4, filtered, and concentrated to give 110 mg (100%) of a clear oil. m/z (ES+) 241 (M+H)+.

Workup

  1. customwas acidified to pH 3-4 at 0° C.
  2. extractionwas extracted with EcOAc (2×50 ml)
  3. dry with materialThe combined organic layers were dried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2429728140d24d91afea687358a57667
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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