Reaktion #2386

Reaktionsgleichung

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

Ausbeute 66.9%

Lösungsmittel

tetrahydrofuran isopropanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooling
2. 2
   Sonstigethe mixture is reacted for two hours
3. 3
   Extraktionextracted with ethyl acetate
4. 4
   WaschenThe ethyl acetate layer is washed
5. 5
   Sonstigedried
6. 6
   Sonstigeevaporated
7. 7
   Sonstigeto remove the solvent
8. 8
   SonstigeThe residue is purified by silica gel column chromatography (solvent; chloroform/methanol=200:1~50:1)
9. 9
   Sonstigecrystallized from diethyl ether

Vorschrift

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).

Quelle