تفاعل #332470

معادلة التفاعل

6-Amino-5-bromo-2-(4-chloro-2-fluoro-3-methoxyphenyl)-pyrimidine-4-carboxylic acid methyl ester

trimethyl((tributylstannyl)ethynyl)silane

→

title compound

المردود 79.4%

6-Amino-2-(4-chloro-2-fluoro-3-methoxyphenyl)-5-trimethylsilanylethynylpyrimidine-4-carboxylic acid methyl ester

المردود 79.4%

المذيبات

1,2-dichloroethane

ظروف التفاعل

المعالجة

1. 1
   أخرىThe cooled reaction mixture
2. 2
   تركيزwas concentrated under vacuum
3. 3
   أخرىthen purified by flash chromatography on silica gel (dichloromethane/ethyl acetate gradient)
4. 4
   أخرىA second purification by flash chromatography on silica gel (hexane/ethyl acetate gradient)

الإجراء التجريبي

6-Amino-5-bromo-2-(4-chloro-2-fluoro-3-methoxyphenyl)-pyrimidine-4-carboxylic acid methyl ester (1.0 g, 2.56 mmol), trimethyl((tributylstannyl)ethynyl)silane (1.98 g, 5.12 mmol), and bis(triphenylphosphine)palladium(II) dichloride (0.18 g, 0.256 mmol) were combined in 1,2-dichloroethane (10 mL) and heated in a CEM microwave reactor at 110° C. for 15 min. The cooled reaction mixture was concentrated under vacuum then purified by flash chromatography on silica gel (dichloromethane/ethyl acetate gradient). A second purification by flash chromatography on silica gel (hexane/ethyl acetate gradient) yielded the title compound (0.829 g, 79% yield): mp 126-128° C.

المصدر