Methanol → HCID 68436311, compound

Participants

Reaction Steps

To a mixture of 4,6-diamino-1-(2-deoxy-β-D-erythro-pentofuranosyl)-3-iodo-1H-pyrazolo[3,4-d]pyrimidine (4.2 g, 10.71 mmol), CuI (211 mg, 1.10 mmol), Pd(PPh3)4 (635 mg, 0.553 mmol), and triethylamine (2.2 mL) in 20 mL of anhydrous DMF was added methyl propargyl ether (1.82 mL). The mixture was stirred under argon for 16 h. and then evaporated to dryness. The residue was crystallized from methanol: 3.20 g (89%) yield; TLC (30% methanol in ethyl acetate), Rf=0.63; 1H NMR (DMSO-d6) δ 7.44 (2H, br d, amino), 6.32 (1H, t, J=6.6 Hz, 1′-H), 6.33 (2H, br s, amino), 5.20 (1H, d, J=4.1 Hz, 3′-OH), 4.75 (1H, br t, 5′-OH), 4.40 (2H, s, methylene), 4.36 (1H, m, 3′-H), 3.76 (1H, m, 4′-H), 3.47 & 3.32 (2H, 2×m, 5′-Hs), 3.32 (3H, s, methoxy), 2.68 & 2.14 (2H, 2×m, 2′-Hs).

Provenance & Evidence