Reaction #1435732

Reaction equation

5-hydroxy-6-(2-chloro-6-fluorophenyl)-7-methylimidazo[1,2-a]pyrimidine

N,N-diethylaniline

phosphorus oxychloride

→

5-chloro-6-(2-chloro-6-fluorophenyl)-7-methylimidazo[1,2-a]pyrimidine

Conditions

Workup

1. 1
   Temperaturewas refluxed
2. 2
   Temperatureunder heating for 26 hours
3. 3
   ConcentrationThe reaction mixture was concentrated
4. 4
   workup.ADDITIONdichloromethane and aqueous saturated sodium bicarbonate solution were added to the residue
5. 5
   WashThe separated organic layer was washed with water
6. 6
   Dryingdried over sodium sulfate
7. 7
   Concentrationconcentrated

Procedure

A mixture of 0.16 g of 5-hydroxy-6-(2-chloro-6-fluorophenyl)-7-methylimidazo[1,2-a]pyrimidine, 0.20 g of N,N-diethylaniline and 2 ml of phosphorus oxychloride was refluxed under heating for 26 hours. The reaction mixture was concentrated, and dichloromethane and aqueous saturated sodium bicarbonate solution were added to the residue. The separated organic layer was washed with water, dried over sodium sulfate and concentrated. The residue was subjected to silica gel chromatography to give 45mg of 5-chloro-6-(2-chloro-6-fluorophenyl)-7-methylimidazo[1,2-a]pyrimidine.

Source