((2S,3S,5R)-5-(2-amino-6-chloro-9H-purin-9-yl)-3-azidotetrahydrofuran-2-yl)methanol → Trans-2-amino-9-(3-azido-2,3-dideoxy-beta-D-erythro-pentofuranosyl)-6((2-phenylcyclopropyl)amino)-9H-purine

Participants

Reaction Conditions

Reaction Steps

Trans-2-phenylcyclopropylamine hydrochloride (Aldrich, lot #01903MK, 2.5 g, 14.7 mmol) was dissolved in 5 mL H2O and the pH adjusted to pH 12. The aqueous solution was extracted with 10 mL EtOAc. The EtOAc was evaporated to dryness and dissolved in 25 mL EtOH. 2-Amino-9-(3-azido-2,3-dideoxy-β-D-erythro-pentofuranosyl)-6-chloro-9H-purine (Example 3d) (0.4 g, 1.29 mmol) was added to the ethanolic solution then placed in a sealed tube and heated at 50° C. for 18 hours. The solvents were removed in vacuo to yield a dark oil. The oil was chromatographed on basic alumina eluted with 1% MeOH in CHCl3. The impure product fractions were combined, evaporated, and rechromatographed on silica gel eluted with 5% MeOH in CHCl3. The collected impure product was again applied to basic alumina eluted with 1% MeOH in CHCl3 to give, after combination and evaporation of appropriate fractions, 0.0802 g (0.2 mMol, 15.5%); mp=65°-70°C.

Provenance & Evidence