3-hydrazinyl-2,5-dimethylPyrazine → 3,6-Dimethylpyrazin-2-amine

HRID 133084Notes

Reaction equation

HRID 133084 reaction equation
[NH:1]([C:3]1[C:4]([CH3:10])=[N:5][CH:6]=[C:7]([CH3:9])[N:8]=1)N>O.[Ni]>[CH3:10][C:4]1[C:3]([NH2:1])=[N:8][C:7]([CH3:9])=[CH:6][N:5]=1

Participants

4

Reactant 1

HCID 152550953-hydrazinyl-2,5-dimethylPyrazine

Product 1

HCID 132615003,6-Dimethylpyrazin-2-amine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 962WaterSolvent2×

Conditions

Temperature
50 °C

Procedure

To a solution of 3-hydrazino-2,5-dimethylpyrazine (2.00 g, 14.5 mmol) from Step A in 75 mL of water was added approximately 1 g (wet) Raney Ni, 50% slurry in water. After stirring at reflux for 2 h, the reaction mixture was filtered hot through Celite, and subsequently washed with hot water, followed by dichloromethane. The concentrated residues were suspended in ethylenediamine and heated at 50° C. for 30 min with stirring. Concentration followed by purification by flash chromatography (silica gel, 50% ethyl acetate/hexane) yielded the title compound. LC/MS 124 (M+1).

Workup

  1. temperatureat reflux for 2 h
  2. filtrationthe reaction mixture was filtered hot through Celite
  3. washsubsequently washed with hot water
  4. stirringwith stirring
  5. concentrationConcentration
  6. customfollowed by purification by flash chromatography (silica gel, 50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-9006e4682cf4447f9bbdb8000dbdb88d
Source dataset
uspto-grants-2008_06
Patent number
US07390809B2

Reaction notes

Loading…