tetramethyl pyrazine-2,3,5,6-tetracarboxylate → 2,3,5,6-Tetramethyl 2,3,5,6-piperazinetetracarboxylate

HRID 2226374Notes

Reaction equation

HRID 2226374 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:10]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[C:8]([C:15]([O:17][CH3:18])=[O:16])=[N:7][C:6]=1[C:19]([O:21][CH3:22])=[O:20])=[O:4]>C(O)C.[Pd]>[CH3:1][O:2][C:3]([CH:5]1[CH:6]([C:19]([O:21][CH3:22])=[O:20])[NH:7][CH:8]([C:15]([O:17][CH3:18])=[O:16])[CH:9]([C:11]([O:13][CH3:14])=[O:12])[NH:10]1)=[O:4]

Participants

4

Reactant 1

HCID 291621tetramethyl pyrazine-2,3,5,6-tetracarboxylate

Product 1

HCID 233626442,3,5,6-Tetramethyl 2,3,5,6-piperazinetetracarboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of tetrakis-methoxycarbonylpyrazine (5.3g, 16.9 mmol) (prepared in accordance with J. Org. Chem. 37 (19) , p2963 (1972)) in 800 ml of dry ethanol, was hydrogenated at 50 bar in the presence of 10 g 5% palladium on charcoal at 80 ° C. for 16 hours. After cooling, the solution was filtered and evaporated to give slightly yellow crystals. Yield: 4.8 g (90%) , mp. 162°-163° C. (Lit. 162°-163° C.). NMR confirmed the structure.

Workup

  1. temperatureAfter cooling
  2. filtrationthe solution was filtered
  3. customevaporated
  4. customto give slightly yellow crystals
  5. customYield: 4.8 g (90%) , mp. 162°-163° C. (Lit. 162°-163° C.)

Sources & evidence

ORD record
ord-7eea1ec8ef014af4b3aad515887c15c5
Source dataset
uspto-grants-1994_09
Patent number
US05348954

Reaction notes

Loading…