Reaction equation
[CH3:1][C:2]1[O:3][CH:4]=[CH:5][C:6]=1[CH3:7].C([Li])CCC.[C:13]([C:15]1[N:20]=[CH:19][CH:18]=[CH:17][N:16]=1)#N.Cl.C([O:24]CC)C>CCCCCC>[CH3:7][C:6]1[CH:5]=[C:4]([C:13]([C:15]2[N:20]=[CH:19][CH:18]=[CH:17][N:16]=2)=[O:24])[O:3][C:2]=1[CH3:1]Participants
Conditions
- Temperature
- -78 °C
Procedure
2,3-Dimethylfuran (1.5 g) was dissolved in diethyl ether (20 ml) under an argon atmosphere to prepare a solution. A 1.6 M hexane solution (10.9 ml) of n-butyllithium was added dropwise to the solution at 0° C., and the mixture was stirred under reflux for 2.5 hr. Thereafter, the reaction solution was cooled to −78° C., a solution of 2-cyanopyrimidine (1.8 g) in diethyl ether (8 ml) was added dropwise thereto, and the mixture was stirred at room temperature overnight. The reaction solution was poured into ice to stop the reaction. The mixture was acidified with 1 M hydrochloric acid and was extracted with ethyl acetate. The ethyl acetate layer was then washed with water and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography using chloroform-acetone to give (4,5-dimethylfuran-2-yl)-(2-pyrimidyl)-methanone (226 mg, yield 7%).
Workup
- customto prepare a solution
- temperatureunder reflux for 2.5 hr
- stirringthe mixture was stirred at room temperature overnight
- additionThe reaction solution was poured into ice
- customthe reaction
- extractionwas extracted with ethyl acetate
- washThe ethyl acetate layer was then washed with water
- dry with materialwas dried over anhydrous sodium sulfate
- customThe solvent was removed by distillation under the reduced pressure
- customthe residue was purified by column chromatography
Sources & evidence
- ORD record
- ord-4c21b05566a24c6c8129ae75418dcaa8
- Source dataset
- uspto-grants-2009_07
- Patent number
- US07560558B2
Linked notes
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