Hydrazine hydrate (1:1) → 1-(5-O-Acetyl-3-azido-2,3-dideoxy-beta-D-erythro-pentofuranosyl)-5-methyl-2-(1H)-pyrimidinone

Participants

Reaction Steps

1-(5-O-Acetyl-3-azido-2,3-dideoxy-β-D-erythro-pentofuranosyl)-5-methyl-4-(1,2,4-triazol-1-yl)-2-(1H)-pyrimidinone (0.5 g, 1.4 mMol) was dissolved in CH3CN (10 mL) and treated with 85% hydrazine hydrate (0.105 g, 2.1 mMol) for 30 minutes at ambient temperature, analogous to the procedure described in (1). The solvents were evaporated in vacuo and the residue chromatographed on silica gel with 9:1 CHCl3 /MeOH (v/v) as the eluting solvent. Collection and evaporation of appropriate fractions yielded a solid. The solid was dissolved in EtOH (50 mL) containing Ag2O (0.35 g, 1.5 mMol, 1.5 eq) and refluxed for 90 minutes. Filtration of the hot suspension through a bed of celite followed by removal of solvents in vacuo gave a solid. The solid was chromatographed on silica gel and eluted with 20:1 CHCl3 /MeOH (v/v). Combination and evaporation of appropriate fractions gave the title compound as a golden oil: UV (nm): at pH 1λmax =327 (ε=6900), λmin =254 (ε=700); at pH 13λmax =322 (ε=17200), λmin =247 (ε=600); 1H NMR: (DMSO-d6) δ8.46(d, J=3.13 Hz, 1H, H4), 7.92(d, J=3.90 Hz, 1H, H6), 6.03(dd, J=5.28 Hz, 6.64 Hz, 1H, H1 ') 4.46-4.03(m, 4H, H3 ', H4 'H5 '), 2.71-2.32(m, 2H, H2 '), 2.05, 2.04(2s, 6H, 5-CH3, acetyl).

Provenance & Evidence