Benzaldehyde → HCID 23503258, compound

Participants

Reaction Steps

A solution of lithium diisopropylamide (13.6 mmol) in tetrahydrofuran/hexane (2:1, 22 ml) was added dropwise to a solution of 5-methyl-7-(2-methylpropyl)thieno[2,3-d]pyridazin-4(5H)-one (example 6 step b, 2.00 g) in tetrahydrofuran (24 ml) at −70° C. under nitrogen. Benzaldehyde (2.00 ml) was added and after 15 minutes, the mixture was warmed to room temperature. 1M Hydrochloric acid (50 ml) was added and the mixture was extracted with ethyl acetate (100 ml). The organic extracts were washed twice with 1M hydrochloric acid, twice with saturated sodium hydrogen carbonate solution, then with brine, dried, filtered and evaporated. The residue was purified by column chromatography, eluting with ethyl acetate:isohexane (1:3 then 1:2 then 1:1), to give the title compound (2.48 g) of which 0.5 g was purified by preparative normal-phase HPLC with gradient ethanol/dichloromethane elution to gave the title compound (0.38 g) as an oil.

Provenance & Evidence