Sodium Azide → 2-Amino-6-azido-9-[2-(2,2-dimethyl-1,3-dioxan-5-yl)ethyl]purine

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-amino-6-chloro-9-[2-(2,2-dimethyl-1,3-dioxan-5-yl)ethyl]purine (0.47 g, 1.5 mmol) in dry N,N-dimethylformamide (5 ml), sodium azide (0.20 g, 3.0 mmol) was added and the mixture was stirred at 100-110° C. for 4 hours. The solvent was removed and the residue washed with water to leave 2-amino-6-azido-9-[2-(2,2-dimethyl-1,3-dioxan-5-yl)ethyl]purine as a crystalline solid (0.36 g, 75%), m.p. decomposed at 200° C.; λmax (MeOH) 272 (ε 8,210) and 301 (ε 10,100) nm; νmax (KBr) 1670, 1625, and 1560 cm−1; δH (CDCl3-CD3OD) 1.44 (6H, s, C(CH3)2), 1.6-2.2 (3H, m, CH2CHCH2), 3.5-3.8 (2H, dd (ABX), J 7 Hz and J 11 Hz, 2×Hax), 3.85-4.15 (2H, dd (ABX), J 4 Hz and J 11 Hz, 2×Heq), 4.29 (2H, t, J 7 Hz, CH2N), and 7.93 (1H, s, 8-H) (Found: C, 48.96; H, 5.66; N, 35.15%; M+ 318.1553. C13H18N8O2 requires C, 49.05; H, 5.70; N, 35.20%; M+ 318.1546).

Provenance & Evidence