Реакция #10346

Уравнение реакции

Sodium hydride

ethylene glycol

4-i-propyl-phenyl sulfamic acid-[6-chloro-5-(o-methoxyphenoxy)-2-(4-pyridyl)-pyrimidin-4-yl]-amide

→

4-i-propyl-phenyl sulfamic acid-[6-(2-hydroxy-ethoxy)-5-(o-methoxyphenoxy)-2-(4-pyridyl)-pyrimidin-4-yl]-amide

Растворители

dimethoxyethane

Условия реакции

Обработка

1. 1
   ДругоеThe solvents were evaporated
2. 2
   workup.ADDITIONwater (10 ml) and a 10% solution of citric acid was added until the pH was 3
3. 3
   Экстракцияfollowed by extraction with EtOAc
4. 4
   СушкаThe organic layers were dried over sodium sulfate
5. 5
   Другоеthe solvent was evaporated
6. 6
   ДругоеThe crude product was purified by chromatography through silicagel with EtOAc

Методика

Sodium hydride (17 mg, 60% dispersion in mineral oil) was added to ethylene glycol (1.2 ml) followed by addition of dimethoxyethane (0.5 ml). Stirring was continued for 30 min, then 4-i-propyl-phenyl sulfamic acid-[6-chloro-5-(o-methoxyphenoxy)-2-(4-pyridyl)-pyrimidin-4-yl]-amide (45 mg, Referential Example 1e)) was added and the reaction mixture was heated to 80° C. for 48 h. The solvents were evaporated, water (10 ml) and a 10% solution of citric acid was added until the pH was 3 followed by extraction with EtOAc. The organic layers were dried over sodium sulfate and the solvent was evaporated. The crude product was purified by chromatography through silicagel with EtOAc to give 4-i-propyl-phenyl sulfamic acid-[6-(2-hydroxy-ethoxy)-5-(o-methoxyphenoxy)-2-(4-pyridyl)-pyrimidin-4-yl]-amide (38 mg). tR=4.56 min, (LC); [M+H]+=552.36 (ES+).

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