Dimethylformamide → 6-(3-H-Benzimidazol-5-yl)methylsulfanyl-9-beta-D-ribofuranosyl-9H-purine

Participants

Reaction Conditions

Reaction Steps

(Cyanomethyl)trimethyl-phosphonium iodide 36 (299 mg, 1.23 mmol) was added to a mixture of alcohol 35 (200 mg, 1.35 mmol), 6-mercaptopurine riboside (284 mg, 1.00 mmol), and DIPEA (0.25 mL) in propionitrile (3 mL). The mixture was heated at 90° C. and some drops of DMF were added to obtain a clear solution. The mixture was stirred overnight at 90° C., cooled to room temperature and water was added. Upon standing at room temperature, 37 was formed as a pale brown precipitate collected by filtration and dried in vacuo (65% yield). 1H NMR (d6-DMSO): δ 8.83, 8.72 (2×s, 2H), 8.21 (s, 1H), 7.70 (s, 1H), 7.54 (d, 1H, J=8.04 Hz), 7.31 (d, 1H, J=8.04 Hz), 6.01 (d, 1H, J=5.85 Hz), 5.57 (d, 1H, J=5.85 Hz), 5.27 (d, 1H, J=5.11 Hz), 5.16 (m, 1H), 4.81 (s, 2H), 4.62 (m, 1H), 4.19 (m, 2H), 3.99 (m, 1H); 13C NMR (d6-DMSO): δ 162.0, 152.8, 149.5, 144.5, 133.7, 132.6, 125.2, 90.5, 87.6, 75.7, 72.2, 63.0, 33.9; Mp: 196-198° C.; HRMS calc. for C18H19N6O4S m/z=415.1200 (M+H), found 415.1155.

Provenance & Evidence