Methyl iodide → HCID 67266934, compound

HRID 598149Notes

Reaction equation

HRID 598149 reaction equation
[NH2:1][C:2]1[C:3]2[CH:11]=[CH:10][N:9]([C:12]3[C:17]([CH3:18])=[CH:16][C:15]([CH3:19])=[CH:14][C:13]=3[CH3:20])[C:4]=2[C:5](=[O:8])[NH:6][N:7]=1.[H-].[Na+].[CH3:23]I>CN(C=O)C.O>[NH2:1][C:2]1[C:3]2[CH:11]=[CH:10][N:9]([C:12]3[C:13]([CH3:20])=[CH:14][C:15]([CH3:19])=[CH:16][C:17]=3[CH3:18])[C:4]=2[C:5](=[O:8])[N:6]([CH3:23])[N:7]=1

Participants

6

Reactant 3

HCID 6328Methyl iodide2×HCID 24758Sodium hydride2×HCID 67266806HCID 67266806, compound

Product 1

HCID 67266934HCID 67266934, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To an ice-cooled solution of 4-amino-1-mesityl-1,6-dihydro-7H-pyrrolo[2,3-d]pyridazin-7-one (268 mg, 1.0 mmol) in DMF (3 ml) was added sodium hydride (60% in oil, 44 mg, 1.1 mmol) and the mixture was stirred for 10 minutes. Methyl iodide (0.081 ml, 1.3 mmol) added and the mixture was stirred at room temperature for 1 hour. Additional sodium hydride (60% in oil, 44 mg, 1.1 mmol) and methyl iodide (0.081 ml, 1.3 mmol) were added and the mixture was stirred for 1 hour. The resulting mixture was diluted with water (30 ml) and extracted with ethyl acetate (30 ml×2). The extracts were combined, washed with water, dried over magnesium sulfate and concentrated in vacuo. The residue was subjected to silica gel column chromatography eluting with hexane/ethyl acetate (1:1-2:3) to give 140 mg (50%) of the title compound as crystals.

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hour
  2. stirringthe mixture was stirred for 1 hour
  3. extractionextracted with ethyl acetate (30 ml×2)
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. washeluting with hexane/ethyl acetate (1:1-2:3)

Sources & evidence

ORD record
ord-a16a8e33589547b5b7041492a77eac64
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

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