Реакция #66695

Уравнение реакции

Sodium bicarbonate

5-(5-Iodo-2-isopropyl-4-methoxy-phenoxy)-pyrimidine-2,4-diamine

furan 2-boronic acid

→

5-(5-Furan-2-yl-2-isopropyl-4-methoxy-phenoxy)-pyrimidine-2,4-diamine

Выход 15.6%

Растворители

dioxane

Условия реакции

Обработка

1. 1
   Другоеcap pressure flask
2. 2
   ТемператураThe reaction mixture was cooled
3. 3
   Другоеpartitioned between water and ethyl acetate
4. 4
   ДругоеThe organic phase was separated
5. 5
   Сушкаdried (MgSO4)
6. 6
   Фильтрацияfiltered
7. 7
   Другоеevaporated under reduced pressure
8. 8
   ДругоеThe residue was purified by flash chromatography (3% to 5% MeOH in methylene chloride with 1% ammonium hydroxide)

Методика

5-(5-Iodo-2-isopropyl-4-methoxy-phenoxy)-pyrimidine-2,4-diamine (400 mg, 1 mmol), furan 2-boronic acid (285 mg, 1.5 mmol) and Pd(Ph3)2Cl2 (50 mg) were taken up in 13 mL of degassed dioxane in a screw cap pressure flask. Sodium bicarbonate (2 mL of 2M aqueous solution) was added, and the reaction mixture was heated to 105° C. for 40 hours. The reaction mixture was cooled and partitioned between water and ethyl acetate. The organic phase was separated, dried (MgSO4), filtered, and evaporated under reduced pressure. The residue was purified by flash chromatography (3% to 5% MeOH in methylene chloride with 1% ammonium hydroxide) to yield 53 mg of 5-(5-Furan-2-yl-2-isopropyl-4-methoxy-phenoxy)-pyrimidine-2,4-diamine. (M+H)=339. Mp=253.7-254.6° C.

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