Water → HCID 69102621, compound

HRID 2217229Notes

Reaction equation

HRID 2217229 reaction equation
[NH2:1][C:2]1[C:3]([C:21]([NH2:23])=[O:22])=[N:4][C:5]([C:14]2[CH:19]=[CH:18][C:17](=[O:20])[NH:16][CH:15]=2)=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:7]=1.[CH:24](I)([CH3:26])[CH3:25].CCOC(C)=O.O>CN(C=O)C.CC([O-])(C)C.[K+]>[NH2:1][C:2]1[C:3]([C:21]([NH2:23])=[O:22])=[N:4][C:5]([C:14]2[CH:19]=[CH:18][C:17](=[O:20])[N:16]([CH:24]([CH3:26])[CH3:25])[CH:15]=2)=[C:6]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:7]=1.[NH2:1][C:2]1[C:3]([C:21]([NH2:23])=[O:22])=[N:4][C:5]([C:14]2[CH:15]=[N:16][C:17]([O:20][CH:24]([CH3:26])[CH3:25])=[CH:18][CH:19]=2)=[C:6]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:7]=1

Participants

8

Reactant 4

HCID 962WaterHCID 6362Isopropyl iodideHCID 8857Ethyl AcetateHCID 69103616HCID 69103616, compound

Product 2

HCID 69102621HCID 69102621, compoundHCID 69102905HCID 69102905, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent3×HCID 23665647Potassium tert-butoxideSolvent

Conditions

Temperature
25 °C

Procedure

3-Amino-6-(6-oxo-1,6-dihydro-3-pyridyl)-5-phenyl-2-pyrazinecarboxamide (92.1 mg) was dissolved in DMF (1 ml) To the solution were added 1M i-PrI solution in DMF (0.33 ml) and 0.1M t-BuOK solution in DMF (3.3 ml). The mixture was stirred at 20-30° C. for 2 hours. The reaction mixture was portioned EtOAc and water. The organic layer was separated. The aqueous layer was extracted with EtOAc. The combined organic solution was washed with brine and dried over MgSO4. Evaporation of solvent gave oily residue. The above residue was purified by chromatography on silica gel (EtOAc only-EtOAc:MeOH=96:4, v/v) to give 3-amino-6-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridyl)-5-phenyl-2-pyrazinecarboxamide (18 mg) and 3-amino-6-(6-isopropoxy-3-pyridyl)-5-phenyl-2-pyrazinecarboxamide (42 mg).

Workup

  1. customThe organic layer was separated
  2. extractionThe aqueous layer was extracted with EtOAc
  3. washThe combined organic solution was washed with brine
  4. dry with materialdried over MgSO4
  5. customEvaporation of solvent
  6. customgave oily residue
  7. customThe above residue was purified by chromatography on silica gel (EtOAc only-EtOAc

Sources & evidence

ORD record
ord-2253cac352eb4e41a1dbcedd352313d7
Source dataset
uspto-grants-2008_08
Patent number
US07407961B2

Reaction notes

Loading…