Réaction #66696

Équation de réaction

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

potassium acetate

thiazole

→

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

Conditions de réaction

Traitement

1. 1
   Autrecap pressure vial
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, 1.0 mmol), potassium acetate ((147 mg), Pd(Ph3)2Cl2 (40 mg in 2 mL dimethyl acetamide) and thiazole were added to a screw cap pressure vial and heated to 155° 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 61 mg of 5-(5-Furan-2-yl-2-isopropyl-4-methoxy-phenoxy)-pyrimidine-2,4-diamine. (M+H)=356. Mp=199.1-203.3° C.

Source