O[CH:2]([CH:20](O)[CH2:21][CH2:22][CH2:23][CH3:24])[CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:16](=[O:17])[C:15]2[N:14]([CH3:18])[CH:13]=[N:12][C:11]=2[N:10]([CH3:19])[C:8]1=[O:9].[BrH:26].[C:27]([OH:30])(=[O:29])[CH3:28].C(=O)(O)[O-].[Na+]>ClCCl>[C:27]([O:30][CH:23]([CH2:24][Br:26])[CH2:22][CH2:21][CH2:20][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:16](=[O:17])[C:15]2[N:14]([CH3:18])[CH:13]=[N:12][C:11]=2[N:10]([CH3:19])[C:8]1=[O:9])(=[O:29])[CH3:28]A mixture of 1-(5,6-dihydroxydecyl)-3,7-dimethylxanthine (2.11 g, 6 mmol) and a 30% solution of hydrogen bromide in acetic acid (3.58 mL, 18 mmol) was stirred for 90 minutes. The mixture was then added to a flask containing aqueous sodium bicarbonate solution (5 g in 40 mL ) and dichloromethane (50 mL). After 10 minutes of vigorous stirring, the layers were separated and the aqueous portion extracted with dichloromethane (2×50 mL). The combined organic phases were dried over sodium sulfate. The solvent was evaporated, yielding 2.72 g (100%) 1-(9-acetoxy-10-bromodecyl)-3,7-dimethylxanthine as a yellow oil. Without further purification, the oil was taken up in methanol (30 mL) and treated with a 1M solution of sodium methoxide (6 mL). After 30 minutes, the reaction mixture was added to water (30 mL) and extracted with dichloromethane (3×50 mL). The organic portions were combined and dried over sodium sulfate to give an off-white solid residue. Recrystalization in dichloromethane/petroleum ether yields 380 mg (91% yield) 1-(9,10-oxidodecyl)-3,7-dimethylxanthine.
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