Hydrochloric Acid → 3,5-Dichloro-2-methylpyrido[3,4-b]pyrazine

HRID 1056245Notes

Reaction equation

HRID 1056245 reaction equation
CS(O[C:6]1[N:11]=[C:10]2[C:12]([Cl:16])=[N:13][CH:14]=[CH:15][C:9]2=[N:8][C:7]=1[CH3:17])(=O)=O.O1CCOCC1.[ClH:24]>CCOC(C)=O>[Cl:24][C:6]1[N:11]=[C:10]2[C:12]([Cl:16])=[N:13][CH:14]=[CH:15][C:9]2=[N:8][C:7]=1[CH3:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 897820325-Chloro-2-methylpyrido[3,4-b]pyrazin-3-yl methanesulfonate

Product 1

HCID 897821093,5-Dichloro-2-methylpyrido[3,4-b]pyrazineYield 49.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A glass microwave reaction vessel was charged with 5-chloro-2-methylpyrido[3,4-b]pyrazin-3-yl methanesulfonate (160 mg, 0.585 mmol), 1,4-Dioxane (1 mL) and hydrogen chloride (4 M in 1,4-dioxane, 0.73 mL, 2.92 mmol) (Sigma Aldich). The reaction mixture was stirred and heated in an oil bath at 70° C. for 1 h, then cooled to RT. The mixture was diluted with EtOAc (50 mL) and washed with sat. NaHCO3. The organic layer was dried (MgSO4), filtered and concentrated to give 3,5-dichloro-2-methylpyrido[3,4-b]pyrazine (62 mg, 0.290 mmol, 49% yield) as a brown solid. MS (ESI, pos. ion) m/z: 213.9 (M+1).

Workup

  1. customA glass microwave reaction vessel
  2. temperaturecooled to RT
  3. washwashed with sat. NaHCO3
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-61fc1946d39b41ea86e5be047daa25b3
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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