Tetrahydrofuran → HCID 59191601, compound
Reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5](Cl)=[C:6]([CH3:9])[C:7]=1[CH3:8].[N:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17]C#N)[CH:12]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].C1C[O:33]CC1>>[Cl:1][C:2]1[N:3]=[N:4][C:5]([C:17]([C:13]2[CH:12]=[N:11][CH:16]=[CH:15][CH:14]=2)=[O:33])=[C:6]([CH3:9])[C:7]=1[CH3:8]Participants
5
Procedure
3,6-Dichloro-4,5-dimethyl-pyridazine (1.00 g, 5.65 mmol) is added to an oven-dried, 250-mL round-bottom flask under N2 followed by THF (50 mL) and pyridin-3-yl-acetonitrile (800 mg, 7.68 mmol). The reaction is degassed with a flow of N2 for 30 min. NaHMDS (14.13 mL, 1.0 M, 14.13 mmol) is added and the reaction is stirred for 16 h. The reaction mixture is then transferred to a beaker and stirred vigorously under open to the atmosphere for several hours. The reaction is quenched with saturated sodium bicarbonate solution, and the organics are extracted with dichloromethane. The combined organic layers are washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The crude material is purified via flash chromatography on silica gel (0-20% methanol in CH2Cl2) to afford the title compound (1.3 g, 93%).