Reacción #2412

Ecuación de reacción

ammonium chloride

4-tert-butylbenzenesulfonyl chloride

5-bromo-6-[2-(5-methylthiopyrimidin-2-yloxy)ethoxy]pyrimidine-4-amine

sodium hydride

→

N-{5-bromo-6-[2-(5-methylthiopyrimidin-2-yloxy)ethoxy]-pyrimidin-4-yl}-4-tert-butylbenzenesulfonamide

Rendimiento 85.5%

Disolventes

water

pyridine

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGThe mixture is stirred at room temperature for 30 minutes
2. 2
   ExtracciónThe mixture is extracted with ethyl acetate
3. 3
   Lavadothe ethyl acetate layer is washed
4. 4
   Otrodried
5. 5
   Otroevaporated
6. 6
   Otroto remove the solvent
7. 7
   OtroThe residue is purified by preparative thin layer chromatography (solvent; chloroform/methanol=15:1)
8. 8
   Otrorecrystallized from hexane/ethyl acetate

Procedimiento

To a solution of 5-bromo-6-[2-(5-methylthiopyrimidin-2-yloxy)ethoxy]pyrimidine-4-amine (102 mg) in tetrahydrofuran (2 ml) is added sodium hydride (60% dispersion-type, 34 mg), and thereto is added 4-tert-butylbenzenesulfonyl chloride (198 mg). The mixture is stirred at room temperature for 20 minutes, and thereto are added a drop of pyridine and water. The mixture is stirred at room temperature for 30 minutes, and neutralized with saturated aqueous ammonium chloride solution. The mixture is extracted with ethyl acetate, and the ethyl acetate layer is washed, dried, and evaporated to remove the solvent. The residue is purified by preparative thin layer chromatography (solvent; chloroform/methanol=15:1), and recrystallized from hexane/ethyl acetate to give N-{5-bromo-6-[2-(5-methylthiopyrimidin-2-yloxy)ethoxy]-pyrimidin-4-yl}-4-tert-butylbenzenesulfonamide (135 mg). The physical properties thereof are the same as those of the compound obtained in Reference Example 16-(4).

Fuente