تفاعل #448701

معادلة التفاعل

6-bromo-1-hexene

Sodium hydride

1-methylthymine

water

→

3-(5-hexenyl)-1-methylthymine

المردود 90.0%

المذيبات

dimethylsulfoxide

ظروف التفاعل

المعالجة

1. 1
   workup.WAITcontinued for 69 hours
2. 2
   استخلاصextracted with dichloromethane (4×50 mL)
3. 3
   غسيلThe combined organic layers were washed with saturated aqueous salt solution (40 mL)
4. 4
   تجفيفdried over sodium sulfate
5. 5
   أخرىThe solvent was evaporated under vacuum
6. 6
   أخرىto give a residue which
7. 7
   أخرىwas crystallized in dichloromethane/ethyl ether

الإجراء التجريبي

This example illustrates a synthesis of 3-(5,6-Oxidohexyl)-1-methylthymine (inventive compound no. 1906). Sodium hydride (343 mg, 14 mmol) was added to a stirring solution of 1-methylthymine (Sigma, 2.00 g, 14 mmol) in dimethylsulfoxide (30 mL). After 15 minutes, 6-bromo-1-hexene (Lancaster, 2.30 g, 14 mmol) was added and stirring continued for 69 hours. The reaction mixture was then poured into water (100 mL) and extracted with dichloromethane (4×50 mL). The combined organic layers were washed with saturated aqueous salt solution (40 mL) and dried over sodium sulfate. The solvent was evaporated under vacuum to give a residue which was crystallized in dichloromethane/ethyl ether to yield 2.80 g (88% yield) 3-(5-hexenyl)-1-methylthymine (inventive compound no. 1905).

المصدر