Sodium Methoxide → HCID 89586553, compound

HRID 1747833Notes

Reaction equation

HRID 1747833 reaction equation
Cl[C:2]1[C:3](=[O:20])[N:4]([C:9]2[N:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:12]=[CH:11][CH:10]=2)[CH:5]=[C:6]([Cl:8])[N:7]=1.[CH3:21][O-:22].[Na+]>CO>[Cl:8][C:6]1[N:7]=[C:2]([O:22][CH3:21])[C:3](=[O:20])[N:4]([C:9]2[N:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:12]=[CH:11][CH:10]=2)[CH:5]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 89586238HCID 89586238, compound

Product 1

HCID 89586553HCID 89586553, compoundYield 58.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3,5-dichloro-1-(1-phenyl-1H-pyrazol-5-yl)pyrazin-2(1H)-one (0.627 g) in methanol (15.0 mL) was added sodium methoxide (0.132 g) at room temperature, and the mixture was stirred for 2 hr. The reaction mixture was concentrated and adjusted to pH 5-6 with 2N hydrochloric acid. The reaction mixture was extracted with dichloromethane. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane/methanol) to give the title compound (0.362 g).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. extractionThe reaction mixture was extracted with dichloromethane
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (dichloromethane/methanol)

Sources & evidence

ORD record
ord-12d9a9a20a214568b25fd93286c13735
Source dataset
uspto-grants-2015_10
Patent number
US09150588B2

Reaction notes

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