Sodium Methoxide → HCID 16070455, compound

HRID 1710713Notes

Reaction equation

HRID 1710713 reaction equation
Br[C:2]1[C:3]([NH2:19])=[N:4][C:5]([C:14]2[O:15][CH:16]=[CH:17][CH:18]=2)=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)[N:7]=1.[CH3:20][O-:21].[Na+]>CO>[O:15]1[CH:16]=[CH:17][CH:18]=[C:14]1[C:5]1[N:4]=[C:3]([NH2:19])[C:2]([O:21][CH3:20])=[N:7][C:6]=1[C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 16070450HCID 16070450, compound

Product 1

HCID 16070455HCID 16070455, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
70 °C

Procedure

3-Bromo-6-(2-furyl)-5-pyridin-4-ylpyrazin-2-amine (Example 62, 160 mg, 0.5 mmol) was suspended in methanol (5 mL), sodium methoxide was added (0.12 mL, solution 30% in methanol, 0.5 mmol) and the solution was heated to 70° C. for 2 hours. The mixture was cooled, the solvent was evaporated in vacuo and the residue was partitioned between dichloromethane and brine. The aqueous layer was extracted with dichloromethane. The organic layer was dried and concentrated. The residue was triturated with diethyl ether to provide the target compound as a brownish solid (62 mg, 46%)

Workup

  1. temperatureThe mixture was cooled
  2. customthe solvent was evaporated in vacuo
  3. customthe residue was partitioned between dichloromethane and brine
  4. extractionThe aqueous layer was extracted with dichloromethane
  5. customThe organic layer was dried
  6. concentrationconcentrated
  7. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-62f50cf1993e4eec948eda2b18012420
Source dataset
uspto-grants-2010_09
Patent number
US07790728B2

Reaction notes

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