Hydrogen Peroxide → HCID 70005572, compound

Participants

Reaction Steps

The TFA salt of 5-amino-1-β-L-ribofuranosylpyrazole-3,4-dicarbonitrile (28) (2.60 g, 10.0 mmol) was dissolved in conc. NH4OH (28%, 100 mL) and treated with H2O2 (30%, 15 mL). The reaction mixture was stirred at room temperature in a pressure bottle for 12 h, and then evaporated to dryness. The residue was co-evaporated with MeOH (3×50 mL). The crude product was crystallized from a mixture of EtOH/water to give 2.0 g (68%) of (29): mp×° C.; 1H NMR (Me2SO-d6) δ3.60 (m, 2H, C5′CH2) 3.87 (m, 1H, C4′H), 4.18 (m, 1H, C3′H), 4.54 (m, 1H, C2′H), 4.91 (t, 1H, C5′OH), 5.03 and 5.38 (2d, 2H, C2′,3′OH), 5.69 (d, 1H, C1′H), 6.99 (br s, 3H, NH2 and CONH(H)), 7.72 and 7.78 (2s, 2H, CONH2), and 9.65 (d, 1H, CON(H)H). Anal. Calc. for C10H15N5O6 (301.26): C, 39.87; H, 5.03; N, 23.25. Found: C, 39.72; H, 5.40; N, 23.61.

Provenance & Evidence