반응 #679587

반응 방정식

1-(2-(2-(2,5-dichloropyrimidin-4-yl)ethyl)phenyl)cyclopropanecarboxamide

1,3-dimethyl-1H-pyrazol-4-amine

p-toluenesulfonic acid monohydrate

→

title compound 26

수율 25.0%

1-(2-(2-(5-Chloro-2-((1,3-dimethyl-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)ethyl)phenyl)cyclopropanecarboxamide

수율 25.0%

용매

1,4-dioxane

1,4-dioxane

반응 조건

후처리

1. 1
   workup.STIRRINGthe reaction mixture was stirred in the microwave at 120° C. for a further 4 hours
2. 2
   기타purified by column chromatography (Biotage Isolera, 24 g SiO2 cartridge, 15-100% EtOAc in petroleum benzine 40-60° C.)
3. 3
   workup.ADDITIONFractions containing suspected product
4. 4
   기타purified by column chromatography (Biotage Isolera, 12 g SiO2, 0-5% MeOH in DCM)

실험 절차

A mixture of 1-(2-(2-(2,5-dichloropyrimidin-4-yl)ethyl)phenyl)cyclopropanecarboxamide A14 (0.100 g, 0.297 mmol), 1,3-dimethyl-1H-pyrazol-4-amine (0.070 g, 0.63 mmol) and p-toluenesulfonic acid monohydrate (0.006 g, 0.032 mmol) in 1,4-dioxane (1.0 mL) was stirred in the microwave at 120° C. for 2 hours. Additional 1,4-dioxane (1.5 mL) was added and the reaction mixture was stirred in the microwave at 120° C. for a further 4 hours. The reaction mixture was adsorbed onto SiO2 and purified by column chromatography (Biotage Isolera, 24 g SiO2 cartridge, 15-100% EtOAc in petroleum benzine 40-60° C.). Fractions containing suspected product were combined and adsorbed onto silica and purified by column chromatography (Biotage Isolera, 12 g SiO2, 0-5% MeOH in DCM) to give the title compound 26 as a pale yellow solid (0.030 g, 25%). LCMS-D: rt 3.24 min; m/z 411 [M+H]+.

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