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

HRID 1952175Notes

Reaction equation

HRID 1952175 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-f658f35adb9143239ca2f37f6a560a55
Source dataset
uspto-grants-2013_03
Patent number
US08404700B2

Reaction notes

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