Triethylamine → HCID 67398550, compound

HRID 869731Notes

Reaction equation

HRID 869731 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[C:5]([CH3:12])=[N:4][C:3]=1[CH2:13][CH2:14][CH3:15].C(N(CC)CC)C>O1CCCC1.[Pd]>[CH3:12][C:5]1[C:6]([C:8]([O:10][CH3:11])=[O:9])=[N:7][CH:2]=[C:3]([CH2:13][CH2:14][CH3:15])[N:4]=1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 86674525HCID 86674525, compound

Product 1

HCID 67398550HCID 67398550, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 6-chloro-3-methyl-5-propylpyrazine-2-carboxylate (3.00 g, 13.1 mmol) and triethylamine (1.83 mL, 13.1 mmol) in tetrahydrofuran (40 mL) was added palladium on carbon (5%, M, wet, 300 mg) at 0° C. under argon. The reaction mixture was stirred for 8 h under hydrogen atmosphere, and then filtrated through celite with tetrahydrofuran. To the filtrate was added manganes dioxide (1.0 g) at room temperature. After being stirred overnight, the reaction mixture was filtrated through celite with tetrahydrofuran. The filtrate was concentrated in vacuo, and the residue was poured into saturated aqueous sodium bicarbonate. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over sodium sulfate, filtrated and concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1 to 13:7) to give methyl 3-methyl-5-propylpyrazine-2-carboxylate. MS (APCI): m/z 195 (M+H).

Workup

  1. filtrationfiltrated through celite with tetrahydrofuran
  2. additionTo the filtrate was added manganes dioxide (1.0 g) at room temperature
  3. stirringAfter being stirred overnight
  4. filtrationthe reaction mixture was filtrated through celite with tetrahydrofuran
  5. concentrationThe filtrate was concentrated in vacuo
  6. additionthe residue was poured into saturated aqueous sodium bicarbonate
  7. extractionThe mixture was extracted with ethyl acetate
  8. washThe organic layer was washed with saturated brine
  9. dry with materialdried over sodium sulfate
  10. filtrationfiltrated
  11. concentrationconcentrated in vacuo
  12. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1 to 13:7)

Sources & evidence

ORD record
ord-cb2008be190643a0b1b73d5e05ea428e
Source dataset
uspto-grants-2015_03
Patent number
US08969376B2

Reaction notes

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