Triphenylphosphine → (E)-2-amino-6-chloro-9-[4-(diisopropoxyphosphoryl)but-3-enyl]purine

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

To a mixture of 2-amino-6-chloropurine (0.6 g, 3.81 mmol) , diisopropyl (E)-4-hydroxybut-1-enylphosphonate (0.90 g, 3.81 mmol) and triphenyl phosphine (2.00 g, 7.62 mmol) in dry N,N-dimethylformamide (30 ml) stirred at 0° C. under dry nitrogen was added diethyl azodicarboxylate (1.33 g, 7.62 mmol). The mixture was allowed to warm to room temperature and stirred for 1.3 hr. The solvent was removed and the residue was purified by column chromatography on silica gel eluting with dichloromethane-methanol (9:1) to afford (E)-2-amino-6-chloro-9-[4-(diisopropoxyphosphoryl)but-3-enyl]purine as a light brown gum (0.52 g, 35%), m.p. 150° C.; λmax (EtOH) 311 (6,760), 249 (5,420) and 224 (24,320)nm; υmax (KBr) 3385, 3320, 3208, 1635, 1615, 1560, 1520, 1410 and 1240 cm-1 ; δH [(CD3) 2 SO] 1.08 (6H, d, J 6 Hz, CH(CH3)2), 1.16 (6H, d, J 6 Hz, CH(CH3)2), 2.77 (2H, m, CH2), 4.27 (4H, m, CH2N and CH(CH3)2), 5.69 (1H, dd, J 17 Hz and 21Hz, PCH=CH), 6.52 (1H, ddt, J 6 Hz, 17 Hz and 22 Hz PCH=CH), 6.89 (2H, br.s, D2O exchangeable, NH2), 8.11 (1H, s, H-8) (Found: MH+ 388.1288. C15H23ClN5O3P requires MH+ 388.1305).

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