Sodium hydride → 6-(2-Hydroxyethoxy)[1,2,4]triazolo[1,5-b]pyridazine

60% Oily sodium hydride (510 mg) was suspended in N,N-dimethylformamide (70 ml), followed by addition of 2-(t-butyldiphenysilyoxy)ethanol (3.83 g). The mixture was stirred at room temperature for 1 hour, followed by addition of 6-chloro[1,2,4]triazolo[1,5-b]pyridazine (1.98 g). The mixture was stirred at room temperature for 5 hours and poured into ice-water, followed by extraction with ethylether. The extract was washed with an aqueous sodium chloride solution, dried over magnesium sulfate and concentrated under reduced pressure. The residue was dissolved in tetrahydrofuran (40 ml), followed by addition of tetra-n-butylammoniumfluoride trihydrate (2.02 g). The mixture was stirred at room temperature for 10 minutes and concentrated under reduced pressure. The residue was subjected to silica-gel column chromatography and eluted with a mixture of ethyl acetate and hexane (1:1). Fractions containing the objective compound were collected and concentrated to yield the title compound (0.875 g).

1. stirringThe mixture was stirred at room temperature for 5 hours
2. extractionfollowed by extraction with ethylether
3. washThe extract was washed with an aqueous sodium chloride solution
4. dry with materialdried over magnesium sulfate
5. concentrationconcentrated under reduced pressure
6. dissolutionThe residue was dissolved in tetrahydrofuran (40 ml)
7. additionfollowed by addition of tetra-n-butylammoniumfluoride trihydrate (2.02 g)
8. stirringThe mixture was stirred at room temperature for 10 minutes
9. concentrationconcentrated under reduced pressure
10. washeluted with a mixture of ethyl acetate and hexane (1:1)
11. additionFractions containing the objective compound
12. customwere collected
13. concentrationconcentrated

ORDレコード

ord-be1750fb7738483cb550ec5dd2efc5e4

出典データセット

uspto-grants-2001_06

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US06248740B1