Phenylhydrazine → HCID 67863089, compound

HRID 2249302Notes

Reaction equation

HRID 2249302 reaction equation
O=[CH:2][C@H:3]([C@H:5]([C@H:7]([CH3:9])[OH:8])[OH:6])[OH:4].NN.O[C:13]1[C:18](N)=[C:17]([NH2:20])N=C(N)N=1.[C:22]1(NN)[CH:27]=CC=C[CH:23]=1.C1(C)C=CC=CC=1[NH:36]N.C1(C)C=CC=C(NN)C=1.C1(C)C=CC(NN)=CC=1.COC1C=CC(NN)=CC=1.ClC1C=CC=CC=1NN.ClC1C=C(NN)C=CC=1.ClC1C=CC(NN)=CC=1>>[C:17]1([NH:20][N:36]=[CH:2][C@H:3]([C@H:5]([C@H:7]([CH3:9])[OH:8])[OH:6])[OH:4])[CH:18]=[CH:13][CH:27]=[CH:22][CH:23]=1

Participants

12

Reactant 11

HCID 7516Phenylhydrazine3×HCID 9321Hydrazine2×HCID 10875(4-Methylphenyl)hydrazineHCID 68256o-TolylhydrazineHCID 68308m-TolylhydrazineHCID 70624(4-Chlorophenyl)hydrazineHCID 75332(3-Chlorophenyl)hydrazineHCID 77023(4-Methoxyphenyl)hydrazineHCID 418422o-Chlorophenylhydrazine hydrochlorideHCID 186467745-Deoxy-L-ribose2×HCID 178508811HCID 178508811, compound

Product 1

HCID 67863089HCID 67863089, compound

Procedure

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.

Workup

  1. customfollowed by oxidation reaction

Sources & evidence

ORD record
ord-ded93db8d875466ba90e3ab8adfa9409
Source dataset
uspto-grants-1991_08
Patent number
US05043446

Reaction notes

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