Ammonium formate → HCID 67482815, compound

HRID 719930Notes

Reaction equation

HRID 719930 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[CH:5]([C:11]1[CH:16]=[N:15][C:14]([N+:17]([O-])=O)=[CH:13][N:12]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].C([O-])=O.[NH4+]>C(O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:20])[CH:5]([C:11]1[CH:16]=[N:15][C:14]([NH2:17])=[CH:13][N:12]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 67482587HCID 67482587, compound

Product 1

HCID 67482815HCID 67482815, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 2-(5-nitro-pyrazin-2-yl)-malonic acid diethyl ester (425 mg, 1.5 mmol) in ethanol (10 mL) at 25° C. was treated with ammonium formate (510 mg, 8.1 mmol) and 10% palladium on activated carbon (51 mg). The mixture was heated to 95–100° C. for 4 h and then was stirred at 25° C. overnight. At this time, the catalyst was removed by filtration through a pad of celite (ethanol wash). The filtrate was concentrated in vacuo. Biotage chromatography (FLASH 40M, Silica, 1/1 ethyl acetate/hexanes) afforded 2-(5-amino-pyrazin-2-yl)-malonic acid diethyl ester (131.5 mg, 37%) as a light tan solid: EI-HRMS m/e calcd for C11H15N3O4 (M+) 253.1063, found 253.1065.

Workup

  1. temperatureThe mixture was heated to 95–100° C. for 4 h
  2. customAt this time, the catalyst was removed by filtration through a pad of celite (ethanol wash)
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-0f9d5641fb0f4171acd284737d1563a6
Source dataset
uspto-grants-2006_11
Patent number
US07132425B2

Reaction notes

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