2-Pyrazineacetic acid, 5-(hydroxyamino)-, ethyl ester → Ethyl 2-(5-aminopyrazin-2-YL)acetate

HRID 2173330Notes

Reaction equation

HRID 2173330 reaction equation
O[NH:2][C:3]1[N:4]=[CH:5][C:6]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[N:7][CH:8]=1>CO.[OH-].[OH-].[Pd+2]>[NH2:2][C:3]1[N:4]=[CH:5][C:6]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[N:7][CH:8]=1

Participants

4

Reactant 1

HCID 1362782792-Pyrazineacetic acid, 5-(hydroxyamino)-, ethyl ester

Product 1

HCID 72212710Ethyl 2-(5-aminopyrazin-2-YL)acetate

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A mixture of ethyl [5-(hydroxyamino)pyrazin-2-yl]acetate (2.8 g, 14.2 mmol) and Pd(OH)2 (3 g, 10%) in 150 mL of methanol was stirred at room temperature under 50 psi of H2 for 2 hours before filtration. The filtrate was concentrated to afford ethyl (5-aminopyrazin-2-yl)acetate. 1H-NMR (400 MHz, CDCl3) δ ppm 7.96 (s, 1H), 7.94 (s, 1H), 4.59 (brs, 2H), 4.18 (q, J=7.2 Hz, 2H), 3.71 (s, 2H), 1.25 (t, J=7.2 Hz, 3H).

Workup

  1. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-676419d3fdd84cb5804ad0d3bdca7647
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

Loading…