Реакция #66497

Уравнение реакции

(RS)—S-(4-aminophenyl)-N-(ethoxycarbonyl)-S-methylsulfoximide

5-bromo-2-chloro-4-methylsulfanyl-pyrimidine

HCl

→

(RS)—N-(ethoxycarbonyl)-(4-{[4-{methylsulfanyl}-5-bromo-pyrimidin-2-yl]amino}phenyl)-S-methylsulfoximide

Растворители

dioxane

acetonitrile water

Условия реакции

Обработка

1. 1
   Другоеconsumption of starting sulfoximine
2. 2
   workup.ADDITIONThe reaction mixture is poured into 800 mL of aq. NaHCO3
3. 3
   Фильтрацияthe pasty precipitate filtered
4. 4
   Промывкаwashed with 70 mL of EtOAc
5. 5
   Другоеcrude material (7.5 g) is recrystallized
6. 6
   Другоеto yield 6 g (35%)

Методика

(RS)—S-(4-aminophenyl)-N-(ethoxycarbonyl)-S-methylsulfoximide (10 g, 42 mmol), 5-bromo-2-chloro-4-methylsulfanyl-pyrimidine (10 g, 42 mmol) and 5M HCl (8 mL) in dioxane is stirred at 60° C. in 90% acetonitrile-water (250 mL) for 36 h. TLC indicates almost complete consumption of starting sulfoximine. The reaction mixture is poured into 800 mL of aq. NaHCO3, the pasty precipitate filtered, washed with 70 mL of EtOAc, then crude material (7.5 g) is recrystallized from boiling EtOH (200 mL) to yield 6 g (35%).

Источник