HCID 70098857, compound → 3-Amino-6-(tetrahydrofuran-2-yl)pyrazine-2-carboxylic acid methyl ester

HRID 467721Notes

Reaction equation

HRID 467721 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:10]([NH2:11])=[N:9][CH:8]=[C:7]([C:12]2[O:13][CH:14]=[CH:15][CH:16]=2)[N:6]=1)=[O:4]>C1COCC1.[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][CH2:14][O:13]2)[N:6]=1)=[O:4]

Participants

4

Reactant 1

HCID 70098857HCID 70098857, compound

Product 1

HCID 700987903-Amino-6-(tetrahydrofuran-2-yl)pyrazine-2-carboxylic acid methyl esterYield 31%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-amino-6-furan-2-yl-pyrazine-2-carboxylic acid methyl ester (1.94 g, 8.9 mmol) was dissolved in THF (80 ml) and hydrogenated over night at rt in the presence of 10% Pd/C (1.0 g). The catalyst was filtered and washed with THF. The filtrate was again hydrogenated in the presence of Pd/C 10% (1.0 g) overnight. The catalyst was filtered and washed with THF. The filtrate was concentrated. The crude product was purified by column chromatography using a CH2Cl2/MeOH gradient for elution, providing the title compound (611 mg, 31%) as yellow solid.

Workup

  1. filtrationThe catalyst was filtered
  2. washwashed with THF
  3. customwas again hydrogenated in the presence of Pd/C 10% (1.0 g) overnight
  4. filtrationThe catalyst was filtered
  5. washwashed with THF
  6. concentrationThe filtrate was concentrated
  7. customThe crude product was purified by column chromatography
  8. washfor elution

Sources & evidence

ORD record
ord-a7c128ccb9b241b29e809a0038e6677d
Source dataset
uspto-grants-2014_01
Patent number
US08623866B2

Reaction notes

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