Phenylhydrazine → HCID 67863089, compound

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Reaction Steps

The resulting 5-deoxy-L-ribose, after reaction with a hydrazine compound is subjected to condensation reaction with an acid addition salt of 4-hydroxy-2,5,6-triaminopyrimidine followed by oxidation reaction. The hydrazine compounds which can be used include phenylhydrazines which may be substituted with C1 -C3 alkyl (substituted or unsubstituted), C1 -C3 alkoxy, halogen, nitro, substituted amino or acyloxy, e.g. phenylhydrazine, o-tolylhydrazine, m-tolylhydrazine, p-tolylhydrazine, 4-methoxyphenylhydrazine, 2-chlorophenylhydrazine, 3-chlorophenylhydrazine and 4-chlorophenylhydrazine, phenylhydrazine being preferable. For example 5-deoxy-L-ribose is reacted with phenylhydrazine in an alcohol (e.g. methanol) to form 5-deoxy-L-ribose phenylhydrazone. This phenylhydrazone is a new compound which has not yet been disclosed in any literature. Then the hydrazone is reacted with e.g. 4-hydroxy-2,5,6-triaminopyrimidine.2HCl in a suitable solvent, e.g. a mixed solution of water and methanol in the presence of 2-mercaptoalcohol (e.g. 2-mercaptoethanol) to form a condensate. The reaction is carried out at a temperature between room temperature and 70° C. for 1-2 hrs. Subsequently the condensate is oxidized for example by addition of an aqueous formic acid solution of iodine, potassium iodide and potassium ferricyanide to give a desired product, l-biopterin.

Provenance & Evidence