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

HRID 1754799Notes

Reaction equation

HRID 1754799 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-21082ac2d8844f249d0da636b7387271
Source dataset
uspto-grants-2015_10
Patent number
US09169250B2

Reaction notes

Loading…