Reaction #70503

Reaction equation

heptane

4-methylbenzylamine

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

sodium carbonate

→

solid

Yield 41.0%

1,4-dichloro-6-(4-methoxybenzyl)-6,7-dihydro-5H-pyrrolo[3,4-d]pyridazine

Yield 41.0%

Solvents

THF

THF

Conditions

Workup

1. 1
   Concentrationconcentrated
2. 2
   workup.DISSOLUTIONThe crude material was dissolved in DCM
3. 3
   Washwashed with water and brine
4. 4
   DryingThe organic 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 (800 mg, 2.39 mmol) in 40 mL anhydrous THF was added with sodium carbonate (507 mg, 4.78 mmol) and tetrabutylammonium iodide (88.3 mg, 0.24 mmol). The reaction mixture was added with 4-methylbenzylamine (0.31 mL, 2.39 mmol) in 20 mL THF dropwisely for 2 h. The reaction mixture was heated at 70° C. for 8 h and concentrated. The crude material was dissolved in DCM and washed with water and brine. The organic 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 (300 mg, yield: 41%).

Source