Reaction equation
[I:1][C:2]1[N:3]=[C:4]([CH3:16])[N:5]([C:8]2[CH:13]=[N:12][N:11]([CH3:14])[C:10](=[O:15])[CH:9]=2)[C:6]=1I.C([Li])CCC>C1COCC1.CCCCCC>[I:1][C:2]1[N:3]=[C:4]([CH3:16])[N:5]([C:8]2[CH:13]=[N:12][N:11]([CH3:14])[C:10](=[O:15])[CH:9]=2)[CH:6]=1Participants
Procedure
A solution of 240 mg (0.543 mmol) 5-(4,5-diiodo-2-methyl-imidazol-1-yl)-2-methyl-2H-pyridazin-3-one in 17 ml of dry THF was cooled to −78° C. and 0.41 ml of a 1.6M solution of n-butyllithium (0.65 mmol) in hexane was added. The mixture was stirred for 5 min., quenched by addition of 0.5 ml of methanol and stirred for an additional 10 min at −78° C. Then 2 ml of saturated ammonium chloride solution was added and the mixture was allowed to warm up to room temperature. After standard workup with ethyl acetate/water, the crude material was purified by flash chromatography on silicagel using a 90:10 mixture of ethyl acetate/heptane as eluant to yield 53 mg (0.168 mmol, 31%) of the title compound as a light yellow solid, MS: m/e=316.9 (M+H+).
Workup
- customquenched by addition of 0.5 ml of methanol
- stirringstirred for an additional 10 min at −78° C
- additionThen 2 ml of saturated ammonium chloride solution was added
- customAfter standard workup with ethyl acetate/water, the crude material was purified by flash chromatography on silicagel
- additiona 90:10 mixture of ethyl acetate/heptane as eluant
Sources & evidence
- ORD record
- ord-7a644990fdfe47308e58b7fc60a61dd9
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08334287B2
Linked notes
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