Iodoethane → HCID 69103003, compound

HRID 2217231Notes

Reaction equation

HRID 2217231 reaction equation
[NH2:1][C:2]1[C:3]([C:21]([OH: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.[CH2:24](I)[CH3:25].[CH3:27][C:28]([O-])(C)C.[K+].[CH3:33][CH2:34][O:35][C:36]([CH3:38])=[O:37]>CN(C=O)C.O>[NH2:1][C:2]1[C:3]([C:21]([O:23][CH2:24][CH3:25])=[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:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:7]=1.[NH2:1][C:2]1[C:38]([C:36]([O:35][CH2:34][CH3:33])=[O:37])=[N:4][C:5]([C:14]2[CH:19]=[CH:18][C:17](=[O:20])[N:16]([CH2:27][CH3:28])[CH:15]=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 6340IodoethaneHCID 8857Ethyl AcetateHCID 23665647Potassium tert-butoxideHCID 69102420HCID 69102420, compound

Product 2

HCID 69103003HCID 69103003, compoundHCID 69103067HCID 69103067, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

3-Amino-6-(6-oxo-1,6-dihydro-3-pyridyl)-5-phenyl-2-pyrazinecarboxylic acid (154 mg) was dissolved in DMF(5 ml). To the solution were added EtI (86.1 mg) and t-BuOK (61.9 mg). 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=95:5, v/v) to give ethyl 3-amino-6-(6-oxo-1,6-dihydro-3-pyridyl)-5-phenyl-2-pyrazinecarboxylate (84 mg) and ethyl 3-amino-6-(1-ethyl-6-oxo-1,6-dihydro-3-pyridyl)-5-phenyl-2-pyrazinecarboxylate (28 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-f4deb702f0a34f2698485c3ab78e4352
Source dataset
uspto-grants-2008_08
Patent number
US07407961B2

Reaction notes

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