Reaction #70504

Reaction equation

heptane

isopropyl amine

4,5-bis(bromomethyl)-3,6-dichloropyridazine

sodium carbonate

→

solid

Yield 58.2%

1,4-dichloro-6-isopropyl-6H-pyrrolo[3,4-d]pyridazine

Yield 58.2%

Solvents

THF

THF

Conditions

Workup

1. 1
   ConcentrationThe reaction mixture was concentrated
2. 2
   workup.DISSOLUTIONdissolved in DCM
3. 3
   Washwashed with water and brine
4. 4
   DryingThe organics solution was dried over Na2SO4
5. 5
   Concentrationconcentrated
6. 6
   Otherto afford a crude oil
7. 7
   OtherThe mixture was purified by flash chromatography on silica gel
8. 8
   Washeluting with 10-80% EtOAc

Procedure

To a suspension of 4,5-bis(bromomethyl)-3,6-dichloropyridazine (700 mg, 2.09 mmol) in 66 mL anhydrous THF was added with sodium carbonate (443 mg, 4.18 mmol) and tetrabutylammonium iodide (77.2 mg, 0.21 mmol). The reaction mixture was added with isopropyl amine (0.18 mL, 2.09 mmol) in 10 mL THF dropwisely for 2 h. The reaction mixture was heated at 70° C. for 3 h. The reaction mixture was concentrated, dissolved in DCM and washed with water and brine. The organics solution was dried over Na2SO4 and concentrated to afford a crude oil. The mixture was purified by flash chromatography on silica gel, eluting with 10-80% EtOAc:heptane to afford a off-white solid (280 mg, yield: 47%).

Source