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R.69 2-Ethylamino-6-methyl-3-(1-naphthylcarbonyl)pyridine Example 1
2-Ethylamino-6-methyl-3-(1-naphthylcarbonyl)pyridine Example 1 Chlorosulfonyl isocyanate (0.8 ml, 9 mmol) was added to a tetrahydrofuran (50 ml) solution of 3-(3-chlorobenzoyl)-6-ethyl-2-ethylaminopyridine (2.6 g, 9 mmol) under ice-cooling, followed by stirring for 1 hour under ice-cooling. To the reaction solution were added water and saturated sodium bicarbonate aqueous solution in that order, followed by 30 minutes of stirring at room temperature. This was adjusted to pH 10 with 1 N sodium hydroxide aqueous solution and extracted with chloroform. After drying the organic layer over anhydrous magnesium sulfate, magnesium sulfate was removed by filtration and the resulting filtrate was concentrated under a reduced pressure. Thereafter, the resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give 4-(3-chlorophenyl)-1,7-diethylpyrido[2,3-d]pyrimidin-2(1H)-one (1.7 g, 60%) in the form of crystals.
2
[ 191219-80-4 ]
[ 34241-39-9 ]
7-(1-bromoethyl)-4-(3-chlorophenyl)-1-ethylpyrido[2,3-d]pyrimidin-2(1H)-one[ No CAS ]
4-(3-chlorophenyl)-7-cyclopropyl-1-ethylpyrido[2,3-d]pyrimidin-2(1H)-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
61%
With N-Bromosuccinimide In tetrachloromethane
21.22 EXAMPLE 23
EXAMPLE 22 4-(3-Chlorophenyl)-7-cyclopropyl-1-ethylpyrido[2,3-d]pyrimidin-2(1H)-one EXAMPLE 23 N-Bromosuccinimide (8.94 g, 50.2 mmol) and 200 mg of 2,2'-azobis(isobutyronitrile) were added to a solution of 15.0 g (47.8 mmol) of 4-(3-chlorophenyl)-1,7-diethylpyrido[2,3-d]pyrimidin-2(1H)-one in 150 ml of carbon tetrachloride, followed by heating under reflux for 3 hours. The reaction solution was again mixed with 1.28 g (7.17 mmol) of N-bromosuccinimide and 100 mg of 2,2'-azobis(isobutyronitrile), followed by heating under reflux for 1 hour. After cooling to room temperature, insoluble matter was removed by filtration, and the resulting filtrate was mixed with water and extracted with carbon tetrachloride. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. After removing magnesium sulfate by filtration, the filtrate was concentrated under a reduced pressure and the resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give 11.5 g of 7-(1-bromoethyl)-4-(3-chlorophenyl)-1-ethylpyrido[2,3-d]pyrimidin-2(1H)-one in the form of crystals. The yield was 61%.
7-(1-acetoxyethyl)-4-(3-chlorophenyl)-1-ethylpyrido[2,3-d]pyrimidin-2(1H)-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
47%
With N-Bromosuccinimide; sodium acetate In methanol; tetrachloromethane; water
24 EXAMPLE 24
EXAMPLE 24 N-Bromosuccinimide (590 mg, 3.3 mmol) and 10 mg of 2,2'-azobis(isobutyronitrile) were added to a solution of 940 mg (3 mmol) of 4-(3-chlorophenyl)-1,7-diethylpyrido[2,3-d]pyrimidin-2(1H)-one in 20 ml of carbon tetrachloride, followed by heating under reflux for 5 hours. The reaction solution was again mixed with 210 mg (1.2 mmol) of N-bromosuccinimide and heated overnight under reflux. Insoluble matter was removed by filtration, and the resulting filtrate was mixed with water and extracted with carbon tetrachloride. The organic layer was washed with brine and dried over anhydrous magnesium sulfate, magnesium sulfate was removed by filtration, and the resulting filtrate was concentrated under a reduced pressure. The thus obtained residue was mixed with 10 ml of methanol and 300 mg of sodium acetate and heated overnight under reflux. The reaction solution was diluted with chloroform and washed with water and brine. The organic layer was dried over anhydrous magnesium sulfate, magnesium sulfate was removed by filtration, and then the resulting filtrate was concentrated under a reduced. pressure. Thereafter, the resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give 520 mg of 7-(1-acetoxyethyl)-4-(3-chlorophenyl)-1-ethylpyrido[2,3-d]pyrimidin-2(1H)-one in the form of crystals. The yield was 47%.