I[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[CH3:8][C:9]1[N:10]([N:15]=C(CC(C)C)C)[C:11](=[O:14])[NH:12][N:13]=1.[C:22](=O)([O-])[O-].[K+].[K+].N1CC(=O)NN=1.N>CN(C)C=O.[Cu]I.O>[NH2:15][N:10]1[C:9]([CH2:8][CH3:22])=[N:13][N:12]([C:2]2[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=2)[C:11]1=[O:14]
For 20 min, a weak stream of argon was passed through a mixture of 1.23 g (6.0 mmol) of 3-iodopyridine, 981 mg (5.0 mmol) of 5-methyl-4-[(4-methylpentan-2-ylidene)amino]-2,4-dihydro-3H-1,2,4-triazol-3-one (preparation cf. EP 511569, WO 1993/004050) and 1.037 g (7.5 mmol) of powdered potassium carbonate in 5 ml of N,N-dimethylformamide. 205 mg (1.0 mmol) of copper(I) iodide were then added, and under protective gas the mixture was heated at 150° C. for 2 hours. Analytically, by thin-layer chromatography, no more triazolinone starting material was found. With stirring, 5 ml of 25% strength ammonia solution and 10 ml of water were added to the cooled reaction mixture, which was then extracted three times in each case with 20 ml of ethyl acetate.
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