Reaction #2364

Reaction equation

Compound A

N-{6-(2-aminoethoxy)-5-(3-methoxyphenoxy)pyrimidin-4-yl}-4-tert-butylbenzenesulfonamide hydrochloride

2-chloropyrimidine

potassium carbonate

dimethylacetamide

→

4-tert-butyl-N-[5-(3-methoxyphenoxy)-6-{2-(2-pyrimidinylamino)ethoxy}-pyrimidin-4-yl]benzenesulfonamide hydrate

Yield 161.1%

Solvents

ammonium chloride

Conditions

Workup

1. 1
   Temperatureis heated
2. 2
   Extractionextracted with ethyl acetate
3. 3
   WashThe extract is washed
4. 4
   Otherdried
5. 5
   OtherThe solvent is evaporated
6. 6
   Otherto remove the solvent
7. 7
   Otherthe residue is purified by silica gel column chromatography (solvent; chloroform/methanol=100:1)
8. 8
   Otherfurther recrystallized from ethyl acetate/n-hexane

Procedure

A mixture of Compound A (150 mg), 2-chloropyrimidine (61 mg), potassium carbonate (122 mg) and dimethylacetamide (1.5 ml) is heated with stirring at 100° C. for three days. The reaction solution is diluted with aqueous ammonium chloride solution, and extracted with ethyl acetate. The extract is washed and dried. The solvent is evaporated to remove the solvent, and the residue is purified by silica gel column chromatography (solvent; chloroform/methanol=100:1) and further recrystallized from ethyl acetate/n-hexane to give 4-tert-butyl-N-[5-(3-methoxyphenoxy)-6-{2-(2-pyrimidinylamino)ethoxy}-pyrimidin-4-yl]benzenesulfonamide hydrate (135 mg) as crystals.

Source