3-Pentanol → 4-(1-Ethylpropoxy)-1-mesityl-6-methyl-1,6-dihydro-7H-pyrrolo[2,3-d]pyridazin-7-one

HRID 598142Notes

Reaction equation

[CH3:1][CH2:2][CH:3]([OH:6])[CH2:4][CH3:5].[H-].[Na+].Cl[C:10]1[C:11]2[CH:20]=[CH:19][N:18]([C:21]3[C:26]([CH3:27])=[CH:25][C:24]([CH3:28])=[CH:23][C:22]=3[CH3:29])[C:12]=2[C:13](=[O:17])[N:14]([CH3:16])[N:15]=1>CN(C=O)C.O>[CH2:2]([CH:3]([O:6][C:10]1[C:11]2[CH:20]=[CH:19][N:18]([C:21]3[C:26]([CH3:27])=[CH:25][C:24]([CH3:28])=[CH:23][C:22]=3[CH3:29])[C:12]=2[C:13](=[O:17])[N:14]([CH3:16])[N:15]=1)[CH2:4][CH3:5])[CH3:1]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 3-pentanol (0.093 ml, 0.86 mmol) in DMF (2 ml) was added sodium hydride (60% in oil, 34 mg, 0.86 mmol). The mixture was stirred for 10 min before addition of 4-chloro-1-mesityl-6-methyl-1,6-dihydro-7H-pyrrolo[2,3-d]pyridazin-7-one (64.8 mg, 0.20 mmol). The mixture was stirred at 60° C. for 1.5 hours, then diluted with water (50 ml) and extracted with ethyl acetate (50 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) to give 52 mg (69%) of the title compound as crystals.

Workup

extractionextracted with ethyl acetate (50 ml)
washThe extract was washed with water
dry with materialdried over magnesium sulfate
concentrationconcentrated in vacuo
customThe residue was purified by silica gel chromatography
washeluting with hexane/ethyl acetate (10:1)

Sources & evidence

ORD record: ord-953709e2e6104a70a9c4bd95a07000b4
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07897607B2

Reaction notes

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