Reaktion #86487

Reaktionsgleichung

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

Ausbeute 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

Ausbeute 54.4%

Lösungsmittel

THF

MeOH

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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]+.

Quelle