تفاعل #2375

معادلة التفاعل

potassium fluoride

N-[6-{2-(4-bromophenoxy)ethoxy}-5-(4-methylphenyl)pyrimidin-4-yl]-4-tert-butylbenzenesulfonamide

(1-ethoxyvinyl)tributyltin

dioxane

→

4-tert-butyl-N-{5-(4-methylphenyl)-6-(2-phenoxyethoxy)pyrimidin-4-yl}benzenesulfonamide

N-[6-{2-(4-acetylphenoxy)ethoxy}-5-(4-methylphenyl)pyrimidin-4-yl]-4-tert-butylbenzenesulfonamide

4-tert-butyl-N-[6-{2-(4-ethoxycarbonylphenoxy)ethoxy}-5-(4-methylphenyl)pyrimidin-4-yl]benzenesulfonamide

المذيبات

ethyl acetate

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةis refluxed for 18 hours
2. 2
   أخرىthe precipitated crystals are removed by filtration
3. 3
   استخلاصThe filtrate is extracted with ethyl acetate
4. 4
   غسيلthe ethyl acetate layer is washed
5. 5
   أخرىdried
6. 6
   تركيزconcentrated to dryness under reduced pressure
7. 7
   أخرىThe residue is purified by silica gel column chromatography (solvent; n-hexane/ethyl acetate=5:1~3:1~1:1)
8. 8
   أخرىeach recrystallized from ethyl acetate/diisopropyl ether

الإجراء التجريبي

A mixture of N-[6-{2-(4-bromophenoxy)ethoxy}-5-(4-methylphenyl)pyrimidin-4-yl]-4-tert-butylbenzenesulfonamide (600 mg), (1-ethoxyvinyl)tributyltin (680 mg), bis(triphenylphosphine)palladium (II) chloride (35.5 mg) and dioxane (24 ml) is refluxed for 18 hours. The mixture is diluted with ethyl acetate, and thereto is added 10% aqueous potassium fluoride solution, and the precipitated crystals are removed by filtration. The filtrate is extracted with ethyl acetate, and the ethyl acetate layer is washed, dried, and concentrated to dryness under reduced pressure. The residue is purified by silica gel column chromatography (solvent; n-hexane/ethyl acetate=5:1~3:1~1:1), and the obtained compounds are each recrystallized from ethyl acetate/diisopropyl ether to give 4-tert-butyl-N-{5-(4-methylphenyl)-6-(2-phenoxyethoxy)pyrimidin-4-yl}benzenesulfonamide (Compound A) (42 mg), N-[6-{2-(4-acetylphenoxy)ethoxy}-5-(4-methylphenyl)pyrimidin-4-yl]-4-tert-butylbenzenesulfonamide (Compound B) (242 mg) and 4-tert-butyl-N-[6-{2-(4-ethoxycarbonylphenoxy)ethoxy}-5-(4-methylphenyl)pyrimidin-4-yl]benzenesulfonamide (Compound C) (58 mg), respectively.

المصدر