Thionyl Chloride → (R)-1-(5-hydroxyhexyl)-8-(2-chloroethylamino)-3-methylxanthine
Reaction equation
C([O:4][C@H:5]([CH3:30])[CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:19](=[O:20])[C:18]2[N:17](COCC)[C:16]([NH:25][CH2:26][CH2:27]O)=[N:15][C:14]=2[N:13]([CH3:29])[C:11]1=[O:12])(=O)C.S(Cl)([Cl:33])=O>>[OH:4][C@H:5]([CH3:30])[CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:19](=[O:20])[C:18]2[NH:17][C:16]([NH:25][CH2:26][CH2:27][Cl:33])=[N:15][C:14]=2[N:13]([CH3:29])[C:11]1=[O:12]Participants
3
Procedure
A mixture of (R)-1-(5-acetoxyhexyl)-7-ethoxymethyl-8-(2-hydroxyethylamino)-3-methylxanthine (3.95 g, 9.3 mmol) and thionyl chloride (25 ml) was stirred at room temperature for 3 hours. After concentrating under reduced pressure to remove unreacted thionyl chloride, ethanol (100 ml) and a 1.0 M solution of hydrogen chloride in diethyl ether (10.0 ml) were added. After the mixture was stirred at 75-80° C. for 16 hours, concentrating under reduced pressure provided (R)-1-(5-hydroxyhexyl)-8-(2-chloroethylamino)-3-methylxanthine (2.2 g, 69% yield) as a white powder.