反应详情

温度

0 °C

3-Pentanol (1.5 ml) was initially charged at RT with stirring and cooled almost to 0° C. with an ice bath. Subsequently, the mixture was admixed with portions of sodium hydride (117 mg). The suspension formed was heated to 55° C. for 1.5 h and then admixed with portions of 6-chloro-7,8-dimethyl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylamine (W2.006a, 100 mg), suspended in 3-pentanol (1 ml) and DMF (1.5 ml). After stirring at 55° C. for 2 h, the mixture was left to stand at RT overnight, admixed with water and extracted three times with dichloromethane. The combined organic phases were dried over sodium sulfate and, after the desiccant had been filtered off, dried under reduced pressure. The residue was purified by means of preparative HPLC (met. A), and the clean product fractions were combined, freed of the acetonitrile under reduced pressure, alkalized with saturated potassium carbonate solution and extracted repeatedly with dichloromethane. The combined organic phases were dried over sodium sulfate, filtered and concentrated. 79 mg of 6-(1-ethylpropoxy)-7,8-dimethyl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylamine and 10 mg of 6-methoxy-7,8-dimethyl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylamine were obtained, which formed in the reaction mixture as a result of contamination with methanol.

1. customThe suspension formed
2. temperaturewas heated to 55° C. for 1.5 h
3. stirringAfter stirring at 55° C. for 2 h
4. waitthe mixture was left
5. extractionextracted three times with dichloromethane
6. dry with materialThe combined organic phases were dried over sodium sulfate
7. filtrationafter the desiccant had been filtered off
8. customdried under reduced pressure
9. customThe residue was purified by means of preparative HPLC (
10. extractionextracted repeatedly with dichloromethane
11. dry with materialThe combined organic phases were dried over sodium sulfate
12. filtrationfiltered
13. concentrationconcentrated