Methyl 3-{[(benzyloxy)carbonyl]amino}-1-methyl-1H-pyrazole-5-carboxylate → methyl 3-amino-1-methyl-1H-pyrazole-5-carboxylate

HRID 1256854Notes

Reaction equation

HRID 1256854 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]([CH3:21])[N:7]=[C:8]([NH:10]C(OCC2C=CC=CC=2)=O)[CH:9]=1)=[O:4]>[Pd].CO>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH3:21])[N:7]=[C:8]([NH2:10])[CH:9]=1)=[O:4]

Participants

4

Reactant 1

HCID 14266058Methyl 3-{[(benzyloxy)carbonyl]amino}-1-methyl-1H-pyrazole-5-carboxylate

Product 1

HCID 13248993methyl 3-amino-1-methyl-1H-pyrazole-5-carboxylateYield 101.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

5-Benzyloxycarbonylamino-2-methyl-2H-pyrazole-3-carboxylic acid methyl ester (643, 2.2 g, 7.6 mmol) was combined with methanol (50 mL) and 10% palladium on carbon (500 mg). The mixture was stirred under an atmosphere of hydrogen for three hours. The mixture was filtered through Celite and the solvent was removed under reduced pressure to give the desired compound (644, 1.2 g, 98%). (ESI) [M+H+]+=156.1.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-53e249f3da0642beb10d020d26e95a73
Source dataset
uspto-grants-2013_06
Patent number
US08461169B2

Reaction notes

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