Chloro-N,N,N',N'-tetramethylformamidinium Hexafluorophosphate → 6-iodo-N,N-dimethyl-[1,2,4]triazolo[4,3-b]pyridazin-3-amine

Participants

Reaction Steps

The 3-hydrazinyl-6-iodopyridazine (1.00 g, 4.24 mmol, prepared using General Procedure D from Example #9, Step A with hydrazine) was dissolved in DMF (10 mL) then N-(chloro(dimethylamino)methylene)-N-methylmethanaminium hexafluorophosphate(V) (1.31 g, 4.66 mmol, Fluka) was added. The solution was stirred for about 5 min and then TEA (1.30 mL, 9.32 mmol) was added. The mixture was stirred at ambient temperature for about 1 h then at about 60° C. for about 2 h. The reaction was concentrated under reduced pressure then the mixture was partitioned between DCM (20 mL) and saturated aqueous NaHCO3. The layers were separated then the organic solution was dried over MgSO4, filtered and concentrated under reduced pressure. The material was purified by flash chromatography on silica gel with DCM/MeOH (95:5) as an eluent. The fractions were collected then concentrated under reduced pressure and the residue was triturated with Et2O (20 mL). The solid was collected by filtration and dried overnight under vacuum to give the title compound (1.01 g, 90%): LC/MS (Table 1, Method g) Rt=1.60 min; MS m/z: 289.8 (M+H)+.

Provenance & Evidence