Reaktion #66497

Reaktionsgleichung

(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

Lösungsmittel

dioxane

acetonitrile water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeconsumption of starting sulfoximine
2. 2
   workup.ADDITIONThe reaction mixture is poured into 800 mL of aq. NaHCO3
3. 3
   Filtrationthe pasty precipitate filtered
4. 4
   Waschenwashed with 70 mL of EtOAc
5. 5
   Sonstigecrude material (7.5 g) is recrystallized
6. 6
   Sonstigeto yield 6 g (35%)

Vorschrift

(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%).

Quelle