Water → 5-(4,6-Dimethoxypyrimidin-2-yl)oxy-4-formyl-3-methylbenzothiophene
Reaction equation
[CH:1]([C:3]1[C:8]2[C:9]([CH3:12])=[CH:10][S:11][C:7]=2[CH:6]=[CH:5][C:4]=1[OH:13])=[O:2].[CH3:14][O:15][C:16]1[CH:21]=[C:20]([O:22][CH3:23])[N:19]=[C:18](S(C)(=O)=O)[N:17]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:14][O:15][C:16]1[CH:21]=[C:20]([O:22][CH3:23])[N:19]=[C:18]([O:13][C:4]2[CH:5]=[CH:6][C:7]3[S:11][CH:10]=[C:9]([CH3:12])[C:8]=3[C:3]=2[CH:1]=[O:2])[N:17]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
A mixture comprising 2.1 g of 4-formyl-5-hydroxy-3-methylbenzothiophene, 2.4 g of 4,6-dimethoxy-2-methylsulfonylpyrimidine and 1.8 g of potassium carbonate in 30 ml of N,N-dimethylformamide, was heated and stirred at 70° C. for 3 hours. The mixture was returned to room temperature, then poured into water and extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous sodium sulfate. Then, it was concentrated under reduced pressure, and the oily substance thereby obtained was purified by silica gel column chromatography (n-hexane/ethyl acetate=10/1) to obtain 3.1 g (yield: 86%) of the desired compound.
Workup
- temperaturewas heated
- customwas returned to room temperature
- extractionextracted with ethyl acetate
- washThe organic layer was washed with water
- dry with materialdried over anhydrous sodium sulfate
- concentrationThen, it was concentrated under reduced pressure
- customthe oily substance thereby obtained
- customwas purified by silica gel column chromatography (n-hexane/ethyl acetate=10/1)
Sources & evidence
- ORD record
- ord-b85621a70dcc4cf1a64757f4dd2df935
- Source dataset
- uspto-grants-1997_04
- Patent number
- US05616537
Reaction notes
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