Water → 1-Methyl-3-(8-nonenyl)thymine

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This example illustrates a synthesis of 1-Methyl-3-(8,9-oxidononyl)thymine (inventive compound no. 1910). Sodium hydride (343 mg, 14 mmol) was added to a stirring solution of 1-methylthymine (2.00 g, 14 nmuol) in dimethylsulfoxide (40 mL). After 15 minutes, 9-bromo-1-nonene (2.93 g, 14 mmol) was added and the mixture stirred for 20 hours. The reaction was poured into 40 mL water and extracted with dichloromethane (3×50 mL). The organic layers were combined, washed with water (40 mL), saturated aqueous salt solution (20 mL), and dried over sodium sulfate. The solvent was evaporated to yield 2.76 g (73% yield) 1-Methyl-3-(8-nonenyl)thymine (inventive compound no. 1917) as a colorless oil which solidified upon standing.

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