Reaction #84656

Reaction equation

tert-butyl ((1S,2R)-2-((6-(2,6-dichloro-3,5-dimethoxyphenyl)quinazolin-2-yl)amino)cyclohexyl)carbamate

TFA

→

(1R,2S)—N1-(6-(2,6-dichloro-3,5-dimethoxyphenyl)quinazolin-2-yl)cyclohexane-1,2-diamine

Solvents

dichloromethane

Conditions

Workup

1. 1
   Otherconsumption of SM
2. 2
   workup.ADDITIONThe reaction mixture was diluted with saturated NaHCO3
3. 3
   Extractionextracted with dichloromethane
4. 4
   DryingThe combined organic layers were dried by Na2SO4
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated

Procedure

A mixture of tert-butyl ((1S,2R)-2-((6-(2,6-dichloro-3,5-dimethoxyphenyl)quinazolin-2-yl)amino)cyclohexyl)carbamate (67 mg, 0.12 mmol) and TFA (0.6 mL) in dichloromethane (0.6 mL) was stirred at room temperature for 60 minutes. LC-MS indicated complete consumption of SM. The reaction mixture was diluted with saturated NaHCO3 and then extracted with dichloromethane. The combined organic layers were dried by Na2SO4, filtered, concentrated to give (1R,2S)—N1-(6-(2,6-dichloro-3,5-dimethoxyphenyl)quinazolin-2-yl)cyclohexane-1,2-diamine which was used without further purification in the next step.

Source