HCID 14042135, compound → HCID 70097075, compound

HRID 2368226Notes

Reaction equation

HRID 2368226 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:10]([NH2:11])=[N:9][CH:8]=[C:7]([C:12]2[CH:16]=[CH:15][O:14][CH:13]=2)[N:6]=1)=[O:4]>CO.[Pd]>[CH3:1][O:2][C:3]([C:5]1[C:10]([NH2:11])=[N:9][CH:8]=[C:7]([CH:12]2[CH2:16][CH2:15][O:14][CH2:13]2)[N:6]=1)=[O:4]

Participants

4

Reactant 1

HCID 14042135HCID 14042135, compound

Product 1

HCID 70097075HCID 70097075, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent

Procedure

A solution of 3-amino-6-(furan-3-yl)-pyrazine-2-carboxylic acid methyl ester (2.9 g, 13.2 mmol) in MeOH (150 ml) was treated with palladium on carbon (10%; 0.6 g, 0.28 mmol) and hydrogenated at 1.2 atmospheres for 40 h. Another 2 equivalents of palladium on carbon were consecutively added and the hydrogenation was continued for another 72 h. The reaction mixture was filtered and the catalyst was washed with MeOH. The solution was concentrated in vacuo and the product was obtained after purification by silica gel chromatography using a heptane/ethyl acetate gradient as light yellow solid (0.3 g, 10%).

Workup

  1. waitthe hydrogenation was continued for another 72 h
  2. filtrationThe reaction mixture was filtered
  3. washthe catalyst was washed with MeOH
  4. concentrationThe solution was concentrated in vacuo
  5. customthe product was obtained
  6. customafter purification by silica gel chromatography

Sources & evidence

ORD record
ord-41627f54c20b4d2caa09e104535e900b
Source dataset
uspto-grants-2014_04
Patent number
US08703768B2

Reaction notes

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