Hydrochloric Acid → 3,6-Dimethylpyrazin-2-amine

HRID 1821790Notes

Reaction equation

HRID 1821790 reaction equation
[N:1]([C:4]1[C:5]([CH3:11])=[N:6][CH:7]=[C:8]([CH3:10])[N:9]=1)=[N+]=[N-].Cl.O.O.[Sn](Cl)(Cl)(Cl)Cl>CO.C(OCC)(=O)C>[NH2:1][C:4]1[C:5]([CH3:11])=[N:6][CH:7]=[C:8]([CH3:10])[N:9]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 130650413-Azido-2,5-dimethylpyrazineHCID 85782573Tin tetrachloride dihydrate

Product 1

HCID 132615003,6-Dimethylpyrazin-2-amineYield 38%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 3-azido-2,5-dimethyl pyrazine (100 mg; 0.66 mmol) in methanol (800 μL) was added 12N HCl (100 μL) and tin chloride dihydrate (149 mg; 0.66 mmol). The reaction was heated to 60° C. and stirred for 12 hours. The reaction was cooled to room temperature, diluted with 50 mL of ethyl acetate and washed with aqueous 10% sodium carbonate (1×50 mL), brine (50 mL), then dried (MgSO4) and filtered. The material was purified using a biotage 12i cartridge eluting with ethyl acetate to yield an off white solid (38% yield).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. washwashed with aqueous 10% sodium carbonate (1×50 mL), brine (50 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customThe material was purified
  6. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-b58e661785134e37a2d62f232f459802
Source dataset
uspto-grants-2009_10
Patent number
US07608618B2

Reaction notes

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