Hydrochloric Acid → 2-Pyrazinamine, 5,6-dichloro-3-(3-pyridinylmethoxy)-

HRID 1444024Notes

Reaction equation

HRID 1444024 reaction equation
[H-].[Na+].[N:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][OH:10])[CH:4]=1.Cl[C:12]1[C:13]([NH2:20])=[N:14][C:15]([Cl:19])=[C:16]([Cl:18])[N:17]=1.Cl>COCOC.O>[Cl:18][C:16]1[N:17]=[C:12]([O:10][CH2:9][C:5]2[CH:4]=[N:3][CH:8]=[CH:7][CH:6]=2)[C:13]([NH2:20])=[N:14][C:15]=1[Cl:19]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 75103-PyridinemethanolHCID 24758Sodium hydrideHCID 133411123,5,6-Trichloro-2-pyrazinamine

Product 1

HCID 591682112-Pyrazinamine, 5,6-dichloro-3-(3-pyridinylmethoxy)-Yield 17.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8020DimethoxymethaneSolvent

Procedure

To a stirred suspension of sodium hydride (1.20 g of a 60% dispersion in oil) in dry dimethoxymethane (40 mL) was added pyridine-3-methanol (2.18 g) in 1,2-dimethoxymethane (10 mL). The resulting suspension was stirred at room temperature for 0.5 h and then 3,5,6-trichloro-2-aminopyrazine (1.2 g) was added and the mixture stirred at 70° C. for 4 h. The reaction mixture was cooled and cautiously added to water (100 mL) and neutralised with 2M hydrochloric acid. The mixture was extracted with ethyl acetate (2×50 mL), dried (MgSO4), filtered and concentrated. The residue was purified by chromatography on silical gel eluting with ethyl acetate to afford the sub-titled compound as a white solid (0.29 g).

Workup

  1. stirringthe mixture stirred at 70° C. for 4 h
  2. temperatureThe reaction mixture was cooled
  3. extractionThe mixture was extracted with ethyl acetate (2×50 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography on silical gel
  8. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-1ede8842ccbd46b9be6d0094986da905
Source dataset
uspto-grants-2010_02
Patent number
US07662825B2

Reaction notes

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