반응 #86487

반응 방정식

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

수율 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

수율 54.4%

용매

THF

MeOH

반응 조건

후처리

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

실험 절차

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]+.

출처