Reacción #2386

Ecuación de reacción

ammonium chloride

4-tert-butyl-N-[6-{2-(5-formylpyrimidin-2-yloxy)ethoxy}-5-(4-methylphenyl)pyrimidin-4-yl]benzenesulfonamide

sodium borohydride

→

4-tert-butyl-N-[6-{2-(5-hydroxymethylpyrimidin-2-yloxy)ethoxy}-5-(4-methylphenyl)pyrimidin-4-yl]benzenesulfonamide

Rendimiento 66.9%

Disolventes

tetrahydrofuran isopropanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooling
2. 2
   Otrothe mixture is reacted for two hours
3. 3
   Extracciónextracted with ethyl acetate
4. 4
   LavadoThe ethyl acetate layer is washed
5. 5
   Otrodried
6. 6
   Otroevaporated
7. 7
   Otroto remove the solvent
8. 8
   OtroThe residue is purified by silica gel column chromatography (solvent; chloroform/methanol=200:1~50:1)
9. 9
   Otrocrystallized from diethyl ether

Procedimiento

To a solution of 4-tert-butyl-N-[6-{2-(5-formylpyrimidin-2-yloxy)ethoxy}-5-(4-methylphenyl)pyrimidin-4-yl]benzenesulfonamide (143 mg) in tetrahydrofuran-isopropanol (4 ml-4 ml) is added sodium borohydride (13 mg) under ice-cooling, and the mixture is reacted for two hours. The mixture is treated with aqueous ammonium chloride solution, and extracted with ethyl acetate. The ethyl acetate layer is washed, dried, and evaporated to remove the solvent. The residue is purified by silica gel column chromatography (solvent; chloroform/methanol=200:1~50:1), and crystallized from diethyl ether to give 4-tert-butyl-N-[6-{2-(5-hydroxymethylpyrimidin-2-yloxy)ethoxy}-5-(4-methylphenyl)pyrimidin-4-yl]benzenesulfonamide (96 mg).

Fuente