Reaction #8692

Reaction equation

4,6-dichloro-2-(4-pyridyl)-5-(p-tolyl)-pyrimidine

2-phenyl-ethanesulfonic acid amide potassium salt

Hunig's base

→

2-phenyl-ethanesulfonic acid (6-chloro-2-pyridin-4-yl-5-p-tolyl-pyrimidin-4-yl)-amide

Yield 21.8%

Solvents

DMSO

water

Conditions

Workup

1. 1
   Extractionextracted twice with diethyl ether
2. 2
   OtherThe precipitate was collected
3. 3
   Otherfurther purified by column chromatography on silica gel eluting with hexane:EA 1:1

Procedure

A solution of 4,6-dichloro-2-(4-pyridyl)-5-(p-tolyl)-pyrimidine (1.5 g), 2-phenyl-ethanesulfonic acid amide potassium salt (1.44 g, Referential Example 1e) and Hunig's base (1 ml) in DMSO (20 ml) was stirred at rt for 24 h before it was diluted with water (150 ml) and extracted twice with diethyl ether. The aqueous layer was acidified with acetic acid. The precipitate was collected, and further purified by column chromatography on silica gel eluting with hexane:EA 1:1 to give 2-phenyl-ethanesulfonic acid (6-chloro-2-pyridin-4-yl-5-p-tolyl-pyrimidin-4-yl)-amide (480 mg) as a foam. LC-MS: tR=5.08 min, [M+1]+=465.13, [M−1]−=462.96.

Source