Réaction #66695

Équation de réaction

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

Rendement 15.6%

Solvants

dioxane

Conditions de réaction

Traitement

1. 1
   Autrecap pressure flask
2. 2
   TempératureThe reaction mixture was cooled
3. 3
   Autrepartitioned between water and ethyl acetate
4. 4
   AutreThe organic phase was separated
5. 5
   Séchagedried (MgSO4)
6. 6
   Filtrationfiltered
7. 7
   Autreevaporated under reduced pressure
8. 8
   AutreThe residue was purified by flash chromatography (3% to 5% MeOH in methylene chloride with 1% ammonium hydroxide)

Mode opératoire

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.

Source