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Stage #1: O-benzylcatechol With sodium hydride In DMF (N,N-dimethyl-formamide) at 0℃; for 0.5h;
Stage #2: 2,5-difluoro-4-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]nitrobenzene In DMF (N,N-dimethyl-formamide) at 0℃; for 1h; |
A mixture of 4.05 g of 2-benzyloxyphenol and 9.5 ml of N,N-dimethylformamide was added dropwise to amixture of 0. 80 g of sodium hydride and 20 ml of N,N-dimethylformamide under ice cooling and the mixture was stirredfor 30 minutes. A mixture of 7.1 g of 2,5-difluoro-4-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]nitrobenzene and 17 ml of N,N-dimethylformamide was added dropwise at the same temperature and the mixturewas stirred for 1 hour. The reaction solution was poured into ice-water and extracted with ethyl acetate. The organiclayer was washed successively once with 1N-HCl and once with saturated aqueous sodium chloride solution, driedover anhydrous magnesium sulfate and concentrated. The residue was subjected to silica-gel column chromatographyto give 8.6 g of 2-(2-benzyloxyphenoxy)-5-fluoro-4-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]nitrobenzene.1H-NMR (CDCl3/250MHz), d (ppm): 3.52 (q,3H,J=1.1Hz), 5.01 (s,2H), 6.31 (s,1H), 6.81 (d,1H,J=6.0Hz), 6.9-7.1 (m,2H), 7.1-7.4 (m,7H), 7.78 (d,1H,J=8.7Hz). |
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Stage #1: O-benzylcatechol With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h;
Stage #2: 2,5-difluoro-4-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]nitrobenzene In DMF (N,N-dimethyl-formamide) at 0℃; |
A mixture of 4.05 g of 2-benzyloxyphenol and 9.5 ml of N,N-dimethylformamide was added dropwise to a mixture of 0.80 g of sodium hydride and 20 ml of N,N-dimethylformamide under ice cooling and the mixture was stirred for 30 minutes. A mixture of 7.1 g of 2,5-difluoro-4-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]nitrobonzene and 17 ml of N,N-dimethylformamide was added dropwise at the same temperature and the mixture was stirred for 1 hour. The reaction solution was poured into ice-water and extracted with ethyl acetate. The organic layer was washed successively once with 1N-HC1 and once with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica-gel column chromatography to give 8.6 g of 2-(2-benzyloxyphenoxy)-5-fluoro-4-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]nitrobenzene.1H-NHR (CDCl3/250MHz), δ (ppm): 3.52 (q,3H,J=1.1Hz), 5.01 (s,2H), 6.31 (s,1H), 6.81 (d,1H,J=6.0Hz), 6.9-7.1 (m,2H), 7.1-7.4 (m,7H), 7.78 (d,1H,J=8.7Hz). |
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Stage #1: O-benzylcatechol With sodium hydride In DMF (N,N-dimethyl-formamide) at 0℃; for 0.5h;
Stage #2: 2,5-difluoro-4-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]nitrobenzene In DMF (N,N-dimethyl-formamide) at 0℃; for 1h; |
A mixture of 4.05 g of 2-benzyloxyphenol and 9.5 ml of N,N-dimethylformamide was added dropwise to a mixture of 0.80 g of sodium hydride and 20 ml of N,N-dimethylformamide under ice cooling and the mixture was stirred for 30 minutes. A mixture of 7.1 g of 2,5-difluoro-4-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]nitrobenzene and 17 ml of N,N-dimethylformamide was added dropwise at the same temperature and the mixture was stirred for 1 hour. The reaction solution was poured into ice-water and extracted with ethyl acetate. The organic layer was washed successively once with 1N-HCl and once with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica-gel column chromatography to give 8.6 g of 2-(2-benzyloxyphenoxy)-5-fluoro-4-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]nitrobenzene.1H-NMR (CDCl3/250MHz), δ (ppm): 3.52 (q,3H, J=1.1Hz), 5.01 (s,2H), 6.31 (s,1H), 6.81 (d,1H, J=6.0Hz), 6.9-7.1 (m,2H), 7.1-7.4 (m,7H), 7.78 (d,1H, J=8.7Hz). |
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Stage #1: O-benzylcatechol With sodium hydride In DMF (N,N-dimethyl-formamide) at 0℃; for 0.5h;
Stage #2: 2,5-difluoro-4-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]nitrobenzene In DMF (N,N-dimethyl-formamide) at 0℃; for 1h; |
A mixture of 4.05 g of 2-benzyloxyphenol and 9.5 ml of N,N-dimethylformamide was added dropwise to a mixture of 0.80 g of sodium hydride and 20 ml of N,N-dimethylformamide under ice cooling and the mixture was stirred for 30 minutes.. A mixture of 7.1 g of 2,5-difluoro-4-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]nitrobenzene and 17 ml of N,N-dimethylformamide was added dropwise at the same temperature and the mixture was stirred for 1 hour.. The reaction solution was poured into ice-water and extracted with ethyl acetate.. The organic layer was washed successively once with 1N-HCl and once with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated.. The residue was subjected to silica-gel column chromatography to give 8.6 g of 2-(2-benzyloxyphenoxy)-5-fluoro-4-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]nitrobenzene.1H-NMR (CDCl3/250MHz), δ (ppm): 3.52 (q,3H,J=1.1Hz), 5.01 (s,2H), 6.31 (s,1H), 6.81 (d, 1H,J=6.0Hz), 6.9-7.1 (m,2H), 7.1-7.4 (m,7H), 7.78 (d, 1H, J=8.7Hz). |
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