Reacción #1546

Ecuación de reacción

5-iodo-6-phenoxy-2-phenyl-4(3H)-pyrimidinone

→

6-phenoxy-2-phenyl-4(3H)-pyrimidinone

Rendimiento 125.6%

Disolventes

acetic acid

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas heated to reflux
2. 2
   TemperaturaThe mixture was maintained
3. 3
   Temperaturaat reflux for 2 h
4. 4
   Temperaturacooled
5. 5
   Filtraciónfiltered
6. 6
   Otroto remove unreacted zinc
7. 7
   Otroto leave a semi-solid which
8. 8
   Otrowas triturated with 75 mL of boiling water

Procedimiento

A mixture of 7.07 g (18.1 mmol) of crude 5-iodo-6-phenoxy-2-phenyl-4(3H)-pyrimidinone, 2.02 g (31.1 mmol) of zinc dust and 25 mL of glacial acetic acid was heated to reflux. After 15 min an additional 2.06 g (31.7 mmol) of zinc dust was added, followed 15 min later by a further 2.04 g (31.4 mmol) of zinc dust. The mixture was maintained at reflux for 2 h, cooled and filtered to remove unreacted zinc. The filtrate was rotovaped to leave a semi-solid which was triturated with 75 mL of boiling water to afford 6.01 g (57% from 4,6-dihydroxy-2-phenylpyrimidine) of 6-phenoxy-2-phenyl-4(3H)-pyrimidinone as a yellow solid. 1H-NMR (d6-DMSO) δ 5.5(1H,s), 7.1-7.5(8H), 8.1(2H).

Fuente