Sodium hydride → 1-Methyl-3-(8-nonenyl)thymine

Participants

Reaction Steps

3-(8,9-Dihydroxynonyl)-1-methylthymine (CT1918) was used as an intermediate for the synthesis of CT1908 (example 12). A mixture of sodium hydride (343 mg, 14 mmol) and 1-methylthymine (2.00 g, 14 mmol) in dimethylsulfoxide (40 ml) was stirred for 15 min and then 9-bromo-1-nonene (2.93 g, 14 mmol) was added. After stirring for 20 hr, the mixture was poured into water (40 ml) and extracted with dichloromethane (3×50 ml). The combined organic layers were washed with water (40 ml), with saturated aqueous sodium chloride solution (20 ml), and dried over sodium sulfate. The solvent was evaporated to give 3-(8-nonenyl)-1-methylthymine (CT1917) (2.76 g, 73% yield) as a colorless oil which solidified upon standing.

Provenance & Evidence