HCID 136404621, compound → HCID 136404620, compound

Participants

Reaction Steps

A mixture of 5-amino-3-(2-deoxy-2-fluoro-3,5-di-O-benzoyl-β-D-arabinofuranosyl)-7-oxothiazolo[4,5-d]pyrimidine-2(3H,6H)-thione (0.18 g, 0.33 mmol), NaOCH3 (0.055 g) and anhydrous MeOH (60 mL) was stirred at room temperature for 16 h with the exclusion of moisture. The reaction mixture was neutralized with Amberlite IR-120(H+) ion-exchange resin. The resin was removed by filtration and the filtrate was evaporated to dryness. The residue was dissolved in MeOH (5 mL), adsorbed onto silica gel (5 g) and loaded on top of a prepacked (in CH2Cl2) silica gel column (2.8×15 cm). The column was flash eluted with CH2Cl2 :MeOH (9:1), the homogeneous product was isolated and crystallized from aqueous EtOH; 0.068 g (0.178 mmol, 54%), mp 240-242° C. (dec). Ir (KBr): ν3210-3410 (OH, NH2), 1685 (C=O), and 1630 (C=S) cm-1 ; Uv, λmax (nm) (ε×10-3): pH 1, 352 (6.5), 291 (3.2), 264 (5.1), 244 (5.4), 216 (5.5); pH 7, 356 (6.2), 264 (5.1), 244 (5.5); pH 11, 356 (6.1), 264 (5.1), 244 (5.6). 1H nmr (DMSO-d6): δ3.74 (m, 3H, C5'H2 and C4'H), 4.72 (t, 1H, C5'OH), 4.90 (m, 1H, C3'H), 5.25 (q, 1H, C2'H), 5.58 (d, 1H, C3'OH), 6.93 (s, 2H, NH2), 7.10 (t, J1',2' =7.6 Hz, 1H, C1'H), 11.53 (s, 1H, NH). Anal. Calc'd for C10H11FN4O4S2.C2H5OH (380.41): C, 37.88; H, 4.50; N, 14.73; S, 16.85; F, 4.99. Found: C, 37.72; H, 4.17; N, 14.93; S, 16.54; F, 5.16.

Provenance & Evidence