Reacción #169014

Ecuación de reacción

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

Rendimiento 15.6%

Disolventes

dioxane

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrocap pressure flask
2. 2
   TemperaturaThe reaction mixture was cooled
3. 3
   Otropartitioned between water and ethyl acetate
4. 4
   OtroThe organic phase was separated
5. 5
   Secadodried (MgSO4)
6. 6
   Filtraciónfiltered
7. 7
   Otroevaporated under reduced pressure
8. 8
   OtroThe residue was purified by flash chromatography (3% to 5% MeOH in methylene chloride with 1% ammonium hydroxide)

Procedimiento

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.

Fuente