反应 #86487

反应方程式

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

收率 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

收率 54.4%

溶剂

THF

MeOH

反应条件

后处理

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

实验过程

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]+.

来源