Sodium Methoxide → 5-Aza-2'-deoxycytidine

Participants

Reaction Steps

A mixture of 4-amino-1-[3,5-di-O-(4-chloro-benzoyl)-2-deoxy-β-D-ribofuranosyl]-1H-[1,3,5]triazin-2-one in about 50% HPLC purity and 4-amino-1-[3,5-di-O-(4-chloro-benzoyl)-2-deoxy-α-D-ribofuranosyl]-1H-[1,3,5]triazin-2-one (6.15 Kg, 12.17 mol) and methanol (21.4 Kg) were charged into a suitable reactor at about 25° C. 30% Sodium methoxide in methanol solution (0.61 Kg) was added to the mixture solution and then stirred for 5 hours. The solids were filtered, washed with methanol (3.3 Kg) and dried at 50° C. for 14 hours to obtain 0.927 Kg (4.11 mol) crude decitabine in 97.1% HPLC purity (about 67% yield based on 4-amino-1-[3,5-di-O-(4-chloro-benzoyl)-2-deoxy-β-D-ribofuranosyl]-1H-[1,3,5]triazin-2-one (compound Ib)).

Provenance & Evidence