Water → 2-(2-Aminopurin-9-yl)methyl butan-1,4-diol

Reaction equation

[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][CH:12]([CH2:17][C:18](OC)=[O:19])[C:13](OC)=[O:14])=[CH:4][N:3]=1.[BH4-].[Li+].O>C(O)(C)(C)C>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][CH:12]([CH2:17][CH2:18][OH:19])[CH2:13][OH:14])=[CH:4][N:3]=1

Participants

Procedure

To a solution of crude dimethyl (2-aminopurin-9-ylmethyl)succinate (3.2 g, 10.9 mmol), dissolved in tert. butanol (250 ml) at 40° C., was added lithium borohydride (1.3 g, 60 mmol) in portions with stirring. After 1 hour at ambient temperature, water (30 ml) was added slowly and stirring continued over night. Inorganic salts were filtered and the solution evaporated to dryness. Yield of crude product was 1.6 g (50%). Chromatography on silica (chloroform+methanol 7+1) afforded pure product.