Water → HCID 58128717, compound

HRID 2088466Notes

Reaction equation

[CH3:1][C:2]1[N:3]([C:8]2[CH:9]=[C:10]([C:15]3[C:16](=[O:21])[NH:17][N:18]=[CH:19][CH:20]=3)[CH:11]=[CH:12][C:13]=2[CH3:14])[C:4]([CH3:7])=[CH:5][CH:6]=1.[CH3:22][Si](C)(C)N[Si](C)(C)C.[K].CI.O>CN(C=O)C>[CH3:7][C:4]1[N:3]([C:8]2[CH:9]=[C:10]([C:15]3[C:16](=[O:21])[N:17]([CH3:22])[N:18]=[CH:19][CH:20]=3)[CH:11]=[CH:12][C:13]=2[CH3:14])[C:2]([CH3:1])=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 4-[3-(2,5-dimethyl-pyrrol-1-yl)-4-methyl-phenyl]-2H-pyridazin-3-one (1.0 g, 3.58 mmol) in DMF (10 ml) was added potassium hexamethyldisilazane (7.88 ml of 0.5M toluene solution, 3.94 mmol) at 0° C. The mixture was stirred at 0° C. for 10 minutes, and methyl iodide (0.267 ml, 4.30 mmol) was added. The mixture was aloud to reach room temperature and was stirred for 24 hours. Water was added and the product was extracted with EtOAc. The combined organic extracts were washed with water and brine, dried over MgSO4, filtered and concentrated to dryness under reduced pressure. Purification of the residue by flash chromatography (hex:EtOAc/6:4) gave 1.05 g (100%) of 4-[3-(2,5-dimethyl-pyrrol-1-yl)-4-methyl-phenyl]-2-methyl-2H-pyridazin-3-one as a yellow solid.

Workup

customto reach room temperature
stirringwas stirred for 24 hours
extractionthe product was extracted with EtOAc
washThe combined organic extracts were washed with water and brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated to dryness under reduced pressure
customPurification of the residue by flash chromatography (hex:EtOAc/6:4)

Sources & evidence

ORD record: ord-22ae183af94244659b6612fbdd6c2e96
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08435990B2

Reaction notes

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