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 Prepartion of Nosantine
  • Prepartion of Nosantine
  • Nosantine (CAS NO.: ), with its systematic name of erythro-9-(1-(1-Hydroxyethyl)heptyl)hypoxanthine, could be produced through many synthetic methods.

    The product could be obtained through the following two ways:Prepartion of NosantinePrepartion of Nosantine

    1) The condensation of 2-aminooctanoic acid (I) with acetic anhydride in pyridine at 100 C produces 3-acetamidononan-2-one (III), which is hydrolyzed with refluxing aqueous concentrated HCl yielding 3-aminononan-2-one hydrochloride (IV). The reduction of (IV) with NaBH4 in methanol gives 3-amino-2-nonanol (V), which is condensed with 4,6-dichloro-5-aminopyrimidine (VI) by means of tributylamine in refluxing pentanol engendering 5-amino-6-(2-hydroxy-3-nonylamino)-4-chloropyrimidine (VII). The cyclization of (VII) with ethyl orthoformate (A) by means of ethanesulfonic acid in refluxing CHCl3 produces 9-(2-hydroxy-3-nonyl)-6-chloropurine (VIII), which is finally hydrolyzed with refluxing aqueous 0.5 N NaOH.
    2) The chloropurine (VIII) is treated with methanolic NH3 at 80-100 C in a pressure vessel to produce 9-(2-hydroxy-3-nonyl)adenine (IX), which is then treated with NaNO2 in acetic acid aqueous HCl.


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