2,3,4,7-polysubstituted naphthyridine [4,3-d] pyrimidine derivates with sterilization activity and preparation thereof
A multi-substitution, pyridine technology, applied in the direction of biocides, chemicals for biological control, biocides, etc., can solve the problem of few research reports on pesticide activity
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Embodiment 1
[0034] Compound 1
[0035] 3-O-fluorobenzyl-5-methyl-4-methylene-7-methylthio-3,4-dihydropyrido[4,3-d]pyrimidine-8-carbonitrile
[0036]
[0037] 15 mmoles of 2-methyl-3-acetyl-5-cyano-6-methylthio-4-pyridinamine were added to a 50-ml reaction flask, and 15 mmoles of triethyl orthoformate were added, at 100 After the reaction was completed, the unreacted triethyl orthoformate and the solvent were distilled off under reduced pressure, and the residue was chromatographed under reduced pressure to obtain white crystal pyridine ether amidine with a melting point of 16.5-16°C and a yield of 65.6%. MS (m / z, %): 277 (M + , 63.21), 199 (31.34), 183 (22.45), 152 (27.81), 77 (100).
[0038] Add 2 mmoles of 2-methyl-3-acetyl-5-cyano-6-methylthiopyridine-4-iminomethylidene ethyl ether, 15 mL of dichloromethane into a 50 mL reaction flask , adding 3 millimoles of o-fluorobenzylamine, stirring and reacting at 20°C for 12 hours, a white solid was precipitated, filtered, recrystallized ...
Embodiment 2
[0100] Compound 8
[0101] 3-Ethyl-5-methyl-4-methylene-7-methoxy-3,4-dihydropyrido[4,3-d]pyrimidine-8-carbonitrile
[0102]
[0103] Add 15 mmoles of 2-methyl-3-acetyl-5-cyano-6-methoxy-4-pyridinamine into a 50 ml reaction flask, add 60 mmoles of triethyl orthoformate, add the catalyst Acetic anhydride was measured and reacted at 130°C for 12 hours. After the reaction was complete, the unreacted triethyl orthoformate was distilled off under reduced pressure, and the residue was chromatographed under reduced pressure to obtain a yellowish crystal of pyridine ether amidine.
[0104] Add 1 mmol of 2-methyl-3-acetyl-5-cyano-6-methoxypyridine-4-iminomethylene ethyl ether, 15 mL of anhydrous DMF into a 50 mL reaction flask , adding 2 mmoles of ethylamine aqueous solution, heated to 120 ° C for 1 hour, a white solid was precipitated, filtered, recrystallized from a mixed solvent of acetone and petroleum ether, and the obtained pure product was a white solid with a yield of 68%. ...
Embodiment 3
[0139] Compound 9
[0140] 3-n-propyl-5-methyl-4-methylene-7-methoxy-3,4-dihydropyrido[4,3-d]pyrimidine-8-carbonitrile
[0141]
[0142] Add 15 mmoles of 2-methyl-3-acetyl-5-cyano-6-methoxy-4-pyridinamine into a 50 ml reaction flask, add 60 mmoles of triethyl orthoformate, add the catalyst P-toluenesulfonic acid was measured and reacted at 130°C for 12 hours. After the reaction was complete, the unreacted triethyl orthoformate was distilled off under reduced pressure, and the residue was chromatographed under reduced pressure to obtain a light yellow crystal of pyridine ether amidine.
[0143] Add 1 mmole of 2-methyl-3-acetyl-5-cyano-6-methoxypyridine-4-imine methylene ethyl ether, 15 ml of anhydrous dioxane to 50 ml of Add 2 mmoles of n-propylamine to the reaction flask, heat to 100° C. for 6 hours to react, a solid is precipitated, filtered, recrystallized in a mixed solvent of acetone and petroleum ether, and the obtained pure product is a yellow solid with a yield of 6...
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