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 Synthesis of Azacitidine
  • Synthesis of Azacitidine
  • (CAS NO.: ), with other name of 2-(beta-D-Ribofuranosyl)-4-amino-1,3,5-triazin-2-one, could be produced through many synthetic methods.

    Following is one of the synthesis routes:

    Synthesis of Azacitidine

    1,2,3,5-Tetra-O-acetyl-beta-D-ribofuranose (I) could react with dry HCl in ether-acetic anhydride to produce 1-chloro-2,3,5-tri-O-acetyl-beta-D-ribofuranose (II), and the yielding product by reaction with silver isocyanate in dry xylene is converted into 2,3,5-tri-O-acetyl-beta-D-ribofuranosylisocyanate (III). The reaction of (III) with 2-methylisourea (IV) in dry CHCl3 affords 1-(2,3,5-tri-O-acetyl-3-D-ribofuranosyl)-4-methylisobiuret (V), which is cyclized by reaction with ethyl orthoformate at 135 C yielding 1-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)-4-methoxy-2-oxo-1,2-dihydro-1,3,5-triazine (VI). At last, this compound is treated with ammonia in dry methanol.


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