Réaction #86487

Équation de réaction

N-(2-((6-(3-(2,6-dichloro-3,5-dimethoxyphenyl)-1-methylureido)pyrimidin-4-yl)amino)-5-(piperazin-1-yl)phenyl)acrylamide 2,2,2-trifluoroacetate

tert-butyl(2-oxoethyl)carbamate

Sodium cyanoborohydride

→

title compound

Rendement 54.4%

tert-butyl (2-(4-(3-acrylamido-4-((6-(3-(2,6-dichloro-3,5-dimethoxyphenyl)-1-methylureido)pyrimidin-4-yl)amino)phenyl)piperazin-1-yl)ethyl)carbamate

Rendement 54.4%

Solvants

THF

MeOH

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGthe reaction mixture was stirred at room temperature over night
2. 2
   AutreSolvent was evaporated
3. 3
   workup.ADDITIONsaturated NaHCO3 solution was added
4. 4
   ExtractionThe mixture was extracted three times with DCM
5. 5
   SéchageCombined organic layer was dried over Na2SO4
6. 6
   Autreevaporated
7. 7
   AutreThe remaining material was purified by flash chromatography on silica eluting with 0% to 15% MeOH in DCM

Mode opératoire

To the solution of N-(2-((6-(3-(2,6-dichloro-3,5-dimethoxyphenyl)-1-methylureido)pyrimidin-4-yl)amino)-5-(piperazin-1-yl)phenyl)acrylamide 2,2,2-trifluoroacetate (Procedure 2L, Example 157) (30 g, 0.042 mmol) in THF (1.0 ml) and MeOH (1.0 ml) was added tert-butyl(2-oxoethyl)carbamate (13 g, 0.08 mmol). The reaction mixture was stirred at room temperature for 10 minutes. Sodium cyanoborohydride (7.0 g, 0.12 mmol) was added and the reaction mixture was stirred at room temperature over night. Solvent was evaporated and saturated NaHCO3 solution was added. The mixture was extracted three times with DCM. Combined organic layer was dried over Na2SO4 and evaporated. The remaining material was purified by flash chromatography on silica eluting with 0% to 15% MeOH in DCM to afford the title compound (17 mg, yield: 54%) ESI-MS: 744 [M+H]+.

Source