Methyl iodide → Methyl (6-methyl-2,5-dioxo-5,6-dihydro-4H-imidazo[1,5,4-de]quinoxalin-1(2H)-yl)acetate

HRID 641382Notes

Reaction equation

HRID 641382 reaction equation
[O:1]=[C:2]1[N:6]2[CH2:7][C:8](=[O:14])[NH:9][C:10]3[CH:11]=[CH:12][CH:13]=[C:4]([C:5]=32)[N:3]1[CH2:15][C:16]([O:18][CH3:19])=[O:17].[C:20](=O)([O-])[O-].[Cs+].[Cs+].IC>CN(C=O)C>[CH3:20][N:9]1[C:10]2[CH:11]=[CH:12][CH:13]=[C:4]3[N:3]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[C:2](=[O:1])[N:6]([C:5]=23)[CH2:7][C:8]1=[O:14]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 86629734Methyl (2,5-di oxo-5,6-dihydro-4H-imidazo[1,5,4-de]quinoxalin-1(2H)-yl)acetate2×

Product 1

HCID 86629738Methyl (6-methyl-2,5-dioxo-5,6-dihydro-4H-imidazo[1,5,4-de]quinoxalin-1(2H)-yl)acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl (2,5-dioxo-5,6-dihydro-4H-imidazo[1,5,4-de]quinoxalin-1(2H)-yl)acetate (300 mg, 1.15 mmol, described in Intermediate 9) in DMF (5 mL) were added cesium carbonate (748 mg, 2.3 mmol) and iodomethane (326 mg, 2.3 mmol). After 16 h, the reaction mixture was quenched with brine (20 mL) and extracted with EtOAc (50 mL). The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo to give the title compound. MS: m/z=276 (M+1).

Workup

  1. customthe reaction mixture was quenched with brine (20 mL)
  2. extractionextracted with EtOAc (50 mL)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8069b60a3736452baef0bc1e634c8fe6
Source dataset
uspto-grants-2010_04
Patent number
US07696192B2

Reaction notes

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