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

HRID 1755963Notes

Reaction equation

HRID 1755963 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 (5.3 g, 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-99063e4947ee44f7af615ba019cf99fc
Source dataset
uspto-grants-1995_08
Patent number
US05439668

Reaction notes

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