Ammonia → HCID 58078371, compound

Participants

Reaction Steps

Compound 16 (0.160 g, 0.386 mmol) was treated with methanolic ammonia (previously saturated at −10° C.), (10 mL) at 100° C. in a stainless-steel bomb for 3 hours, then cooled to room temperature. The solvent was evaporated under reduced pressure and the residue was partitioned between methylene chloride (30 mL) and water (30 mL). The aqueous layer was washed with methylene chloride (2×30 mL), concentrated under reduced pressure. The crude material was purified by silica gel column chromatography [eluent: 20% methanol in methylene chloride] to afford 1-(4-C-methyl-β-D-ribofuranosyl)-5-methyl-cytosine (60 mg, 57%). This compound was dissolved in EtOH 100 (1.5 mL), treated with a 2N hydrochloric acid solution (0.3 mL), and the mixture was stirred before being concentrated under reduced pressure. The procedure was repeated twice and 17 was precipitated from absolute ethanol. Mp: 194–200 (dec.); UV (H2O): λmax=275.6 nm (ε=7300), λmin=255 nm (ε=4700); HPLC 100%, 1H-NMR (DMSO-d6): δ 9.34 and 9.10 (2s, 2H, NH2), 8.21 (s, 1H, H-6), 5.80 (d, 1H, H-1′, J1′-2′=6.0 Hz), 5.3–4.3 (m, 3H, OH-2′, OH-3′ and OH-5′), 4.21 (t, 1H, H-2′, J=5.7 Hz), 3.98 (d, 1H, H-3′, J=5.3 Hz), 3.5–3.3 (m, 2H, H-5′ and H-5″), 1.97 (s, 3H, CH3), 1.12 (s, 3H, CH3).

Provenance & Evidence