Reaction #40559

Reaction equation

NaHCO3

6-Chloro-4-(6-formyl-1-(2-trimethylsilanylethoxymethyl)-1H-benzimidazol-2-yl]-2-(2-trimethylsilanylethoxymethyl)-2H-pyridazin-3-one

4-Methylpiperazine

CO2

sodium triacetoxyborohydride

→

6-Chloro-4-(6-(4-methylpiperazin-1-ylmethyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzimidazol-2-yl]-2-(2-trimethylsilanylethoxymethyl)-2H-pyridazin-3-one

Solvents

dichloromethane

dichloro-methane

acetic acid

Conditions

Workup

1. 1
   Extractionthe aqueous phase is extracted with dichloromethane
2. 2
   DryingThe combined organic phases are dried with MgSO4
3. 3
   Otherthe solvent is removed in a rotary evaporator

Procedure

6-Chloro-4-(6-formyl-1-(2-trimethylsilanylethoxymethyl)-1H-benzimidazol-2-yl]-2-(2-trimethylsilanylethoxymethyl)-2H-pyridazin-3-one is dissolved in dichloro-methane. 4-Methylpiperazine and acetic acid are added. After 15 minutes, sodium triacetoxyborohydride is added in several portions over the course of 3 hours. After conversion is complete, saturated aqueous NaHCO3 solution is added and the reaction solution is stirred until no further CO2 evolution is observed. It is diluted with dichloromethane, and the aqueous phase is extracted with dichloromethane. The combined organic phases are dried with MgSO4, and the solvent is removed in a rotary evaporator.

Source