Methyl iodide → HCID 58938671, compound

HRID 598148Notes

Reaction equation

HRID 598148 reaction equation
[C:1]1([CH3:23])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[N:9]1[C:13]2[C:14](=O)[NH:15][N:16]=[C:17]([NH:18][CH2:19][CH2:20][CH3:21])[C:12]=2[CH:11]=[CH:10]1.[CH3:24]I.[C:26](=[O:29])([O-])[O-].[K+].[K+].[H-].[Na+]>O.CN(C=O)C>[C:3]1([CH3:8])[CH:4]=[C:5]([CH3:7])[CH:6]=[C:1]([CH3:23])[C:2]=1[N:9]1[C:13]2[C:26](=[O:29])[N:15]([CH3:14])[N:16]=[C:17]([N:18]([CH3:24])[CH2:19][CH2:20][CH3:21])[C:12]=2[CH:11]=[CH:10]1

Participants

7

Reactant 4

HCID 6328Methyl iodide2×HCID 11430Potassium CarbonateHCID 24758Sodium hydrideHCID 58938661HCID 58938661, compound

Product 1

HCID 58938671HCID 58938671, compoundYield 20.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
60 °C

Procedure

A mixture of 1-mesityl-4-(propylamino)-1,6-dihydro-7H-pyrrolo[2,3-d]pyridazin-7-one (29.8 mg, 0.092 mmol), methyl iodide (0.011 ml, 0.18 mmol), potassium carbonate (25.4 mg, 0.18 mmol) and DMF (1 ml) was stirred at 60° C. for 4 hours. The mixture was diluted with water (30 ml) and extracted with ethyl acetate (30 ml). The extract was washed with water, dried over magnesium sulfate and concentrated in vacuo. A mixture of the residue, methyl iodide (0.1 ml), sodium hydride (60% in oil, 8 mg, 0.2 mmol) and DMF (2 ml) was stirred room temperature for 3 hours. The mixture was diluted with water (30 ml) and extracted with ethyl acetate (30 ml). The extract was washed with water, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with hexane/ethyl acetate (10:1-5:1) to give 6.5 mg (20%) of the title compound as crystals.

Workup

  1. extractionextracted with ethyl acetate (30 ml)
  2. washThe extract was washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. stirringwas stirred room temperature for 3 hours
  6. extractionextracted with ethyl acetate (30 ml)
  7. washThe extract was washed with water
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by silica gel chromatography
  11. washeluting with hexane/ethyl acetate (10:1-5:1)

Sources & evidence

ORD record
ord-da771e24119b4e488b6c66c4642f2650
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

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