تفاعل #2386

معادلة التفاعل

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

المردود 66.9%

المذيبات

tetrahydrofuran isopropanol

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةcooling
2. 2
   أخرىthe mixture is reacted for two hours
3. 3
   استخلاصextracted with ethyl acetate
4. 4
   غسيلThe ethyl acetate layer is washed
5. 5
   أخرىdried
6. 6
   أخرىevaporated
7. 7
   أخرىto remove the solvent
8. 8
   أخرىThe residue is purified by silica gel column chromatography (solvent; chloroform/methanol=200:1~50:1)
9. 9
   أخرىcrystallized from diethyl ether

الإجراء التجريبي

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).

المصدر