Methanol → HCID 66665855, compound

HRID 406269Notes

Reaction equation

HRID 406269 reaction equation
Cl[C:2]1[CH:25]=[N:24][C:5]2=[N:6][C:7]([C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=3)=[C:8]([C:10]3[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=3)[N:9]=[C:4]2[CH:3]=1.[Na].[CH3:27][OH:28]>C(Cl)Cl>[CH3:27][O:28][C:2]1[CH:25]=[N:24][C:5]2=[N:6][C:7]([C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=3)=[C:8]([C:10]3[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=3)[N:9]=[C:4]2[CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 5360545Sodium2×HCID 666663497-Chloro-2,3-dip-tolylpyrido[2,3-b]pyrazine

Product 1

HCID 66665855HCID 66665855, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture comprising 7-chloro-2,3-dip-tolylpyrido[2,3-b]pyrazine (836 mg, 2.417 mmol) in dry MeOH (10 ml) and DCM (5 ml) bubbled through with nitrogen was treated portionwise with sodium (278 mg, 12.09 mmol). The resulting mixture was heated at reflux overnight. A further portion of sodium (278 mg, 12.09 mmol) was added and refluxing continued overnight. After cooling to RT, the solvent was removed in vacuo and the resulting residue was added to water. The mixture was extracted with DCM (×3) and the combined organic extracts were washed with brine, dried over MgSO4 and concentrated in vacuo. Purification by chromatography on silica eluting with 10-40% EtOAc/iso-hexane afforded the title compound;

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux overnight
  3. temperaturerefluxing continued overnight
  4. customthe solvent was removed in vacuo
  5. additionthe resulting residue was added to water
  6. extractionThe mixture was extracted with DCM (×3)
  7. washthe combined organic extracts were washed with brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated in vacuo
  10. customPurification by chromatography on silica eluting with 10-40% EtOAc/iso-hexane

Sources & evidence

ORD record
ord-c4d2b2e413f048fca0fff1a2cf68a1dc
Source dataset
uspto-grants-2014_06
Patent number
US08754085B2

Reaction notes

Loading…