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

HRID 1094087Notes

Reaction equation

HRID 1094087 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-33d46a0d47b94d11a939ad761f500907
Source dataset
uspto-grants-2012_03
Patent number
US08133891B2

Reaction notes

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