تفاعل #58365

معادلة التفاعل

sodium carbonate

4-chloro-8-(2,6-difluorophenyl)-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one

4-fluorobenzeneboronic acid

→

title compound

المردود 63.0%

8-(2,6-Difluorophenyl)-4-(2-methylphenyl)-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one

المردود 63.0%

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   أخرىThe mixture was irradiated with microwave at about 150° C. for about 20 min
2. 2
   ترشيحfiltered
3. 3
   أخرىthe filtrate evaporated
4. 4
   workup.DISSOLUTIONThe crude product was redissolved in ethyl acetate (10 mL)
5. 5
   أخرىThe layers were separated
6. 6
   تجفيفthe organic layer was dried over magnesium sulphate
7. 7
   ترشيحfiltered
8. 8
   أخرىevaporated
9. 9
   أخرىThe crude product was purified by flash chromatography on silica gel with cyclohexane
10. 10
    workup.ADDITIONcontaining ethyl acetate (0 to 50%)

الإجراء التجريبي

THF (10 mL) and 2M sodium carbonate (2 mL) were added to a mixture of 4-chloro-8-(2,6-difluorophenyl)-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one (0.34 g, 1.0 mmol, solid-supported tetrakis(triphenylphosphine)palladium(0) (0.39 g, 0.1 mmol) and 4-fluorobenzeneboronic acid (0.21 g, 1.5 mmol). The mixture was irradiated with microwave at about 150° C. for about 20 min, then filtered and the filtrate evaporated. The crude product was redissolved in ethyl acetate (10 mL) and water (10 mL). The layers were separated and the organic layer was dried over magnesium sulphate, filtered and evaporated. The crude product was purified by flash chromatography on silica gel with cyclohexane containing ethyl acetate (0 to 50%) to give the title compound (0.25 g, 63%). LC-MS m/z 396 (M+H)+, 3.55 min (ret time).

المصدر