반응 #86483

반응 방정식

tert-butyl 4-(3-acrylamido-4-((tert-butoxycarbonyl)(6-(3-(2,6-dichloro-3,5-dimethoxyphenyl)-1-methyl-3-((2-(trimethylsilyl)ethoxy)methyl)ureido)pyrimidin-4-yl)amino)phenyl)piperazine-1-carboxylate

TFA

NH4OH

→

title compound

수율 94.2%

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

수율 94.2%

용매

DCM

반응 조건

후처리

1. 1
   기타The reaction mixture was evaporated
2. 2
   workup.DISSOLUTIONThe remaining residue was dissolved in DCM
3. 3
   세척washed with saturated NaHCO3
4. 4
   건조dried over MgSO4
5. 5
   기타evaporated
6. 6
   workup.DISSOLUTIONThe resulting material was dissolved in THF (2.0 ml)
7. 7
   workup.STIRRINGThe reaction mixture was stirred at room temperature for 5 minutes
8. 8
   기타The reaction mixture was evaporated

실험 절차

tert-butyl 4-(3-acrylamido-4-((tert-butoxycarbonyl)(6-(3-(2,6-dichloro-3,5-dimethoxyphenyl)-1-methyl-3-((2-(trimethylsilyl)ethoxy)methyl)ureido)pyrimidin-4-yl)amino)phenyl)piperazine-1-carboxylate (59 g, 0.06 mmol) was stirred in DCM (2.0 ml). TFA (97 μl, 1.3 mmol) was added and the mixture was stirred at room temperature for 6 hours. The reaction mixture was evaporated. The remaining residue was dissolved in DCM and washed with saturated NaHCO3, dried over MgSO4 and evaporated. The resulting material was dissolved in THF (2.0 ml) and NH4OH (74 μl, 1.9 mmol) was added. The reaction mixture was stirred at room temperature for 5 minutes. The reaction mixture was evaporated to obtain the title compound (34 mg, yield: 90%) which was taken to the next step without further purification. 1H-NMR (400 MHz, DMSO-d) δ 2.62 (br. s., 4H) 3.08-3.27 (m, 7H) 3.77-4.03 (m, 6H) 5.72 (d, 1H) 6.11-6.34 (m, 2H) 6.40-6.62 (m, 1H) 6.70-6.98 (m, 2H) 7.22-7.37 (m, 2H) 8.32 (s, 1H) 8.70 (s, 1H) 9.58 (br. s., 1H) 12.06 (s, 1H); ESI-MS: 601 [M+H]+.

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