Reacción #4773

Ecuación de reacción

5-(1-hydroxyethyl)-6-methyl-4-(3-nitrophenyl)-2-phenylpyrimidine

phosphorus tribromide

→

5-(1-bromoethyl)-6-methyl-4-(3-nitrophenyl)-2-phenylpyrimidine

Disolventes

tetrahydrofuran

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónextracted with ethyl acetate
2. 2
   OtroThe organic layer was evaporated in vacuo
3. 3
   OtroThe residue was chromatographed on silicagel
4. 4
   Lavadoeluting with chloroform
5. 5
   workup.ADDITIONThe fractions containing the desired product
6. 6
   Otroevaporated in vacuo
7. 7
   OtroThe residue was crystallized from diisopropyl ether

Procedimiento

A solution of 5-(1-hydroxyethyl)-6-methyl-4-(3-nitrophenyl)-2-phenylpyrimidine (1.8 g) in tetrahydrofuran (10 ml) was dropped to a solution of phosphorus tribromide (0.34 ml) in tetrahydrofuran (20 ml) under ice cooling. The reaction mixture was stirred for 5 hours at the same condition and poured into ice water and extracted with ethyl acetate. The organic layer was evaporated in vacuo. The residue was chromatographed on silicagel eluting with chloroform. The fractions containing the desired product were combined and evaporated in vacuo. The residue was crystallized from diisopropyl ether to afford 5-(1-bromoethyl)-6-methyl-4-(3-nitrophenyl)-2-phenylpyrimidine (0.3 g).

Fuente