Diisopropylethylamine → 6-(Benzothiazol-6-yl)methylsulfanyl-9-(beta-d-ribofuranosyl)purine

Participants

Reaction Conditions

Reaction Steps

(Cyanomethyl)trimethylphosphonium iodide (45 mg) was added to a mixture of 40 (Burger, A.; Sawhney, S. N. J. Med. Chem. 1968, 11, 270-273) (33 mg, 0.2 mmol), 6-mercaptopurine riboside (42 mg, 0.2 mmol) and DIPEA (0.04 ml) in 0.43 ml of propionitrile. The mixture was heated at 90° C. and few drops of DMF were added to obtain a clear solution. Stirring was continued overnight at 90° C. The mixture was cooled to room temperature, water was added and slowly a pale brown precipitate was formed. The solid was collected and dried under vacuum. 1H NMR (CD3OD): δ9.20, 8.74 (2×s, 2H), 8.59 (s, 1), 8.18 (s, 1H), 7.98 (d, 1H, J=8.78 Hz), 7.67 (d, 1H, J=8.77 Hz), 6.07 (d, 1H, J=5.11 Hz), 4.84 (s, 2H), 4.72 (m, 1H), 4.35 (m, 1H), 4.17 (m, 2H), 3.83 (m, 1H);13C-NMR (CDCl3/d6-DMSO): 6161.5, 157.1, 153.5, 152.8, 149.5, 144.6, 137.4, 135.2, 129.0, 124.0, 123.7, 90.6, 87.6, 75.7, 72.2, 63.0, 33.2, 19.4; Mp=decomp. 140° C.; HRMS calc. for C18H18N5O4S2 m/Z=432.5100 (M+H), found 432.0787.

Provenance & Evidence