Propionic Acid → 5-amino-1-beta-D-ribofuranosyl-4-cyanoimidazole

HRID 847764Notes

Reaction equation

HRID 847764 reaction equation
[NH2:1][C:2]1[N:6]([C@@H:7]2[O:13][C@H:12]([CH2:14][OH:15])[C@@H:10]([OH:11])[C@H:8]2[OH:9])[CH:5]=[N:4][C:3]=1[C:16]([NH2:18])=O.C(O)(=O)CC.NC1N([C@@H]2O[C@H](COC(=O)CC)[C@@H](OC(=O)CC)[C@H]2OC(=O)CC)C=NC=1C(N)=O.NC1N([C@@H]2O[C@H](COC(=O)CC)[C@@H](OC(=O)CC)[C@H]2OC(=O)CC)C=NC=1C#N>>[NH2:1][C:2]1[N:6]([C@@H:7]2[O:13][C@H:12]([CH2:14][OH:15])[C@@H:10]([OH:11])[C@H:8]2[OH:9])[CH:5]=[N:4][C:3]=1[C:16]#[N:18]

Participants

5

Reactant 4

HCID 1032Propionic AcidHCID 17513AcadesineHCID 128763565-amino-1-(2,3,5,-tri-O-propionyl-beta-D-ribofuranosyl)imidazole-4-carboxamideHCID 129475215-amino-4-cyano-1-(2,3,5-tri-O-propionyl-beta-D-ribofuranosyl)imidazole

Product 1

HCID 109775505-amino-1-beta-D-ribofuranosyl-4-cyanoimidazole

Procedure

A method according to claim 8, wherein 5-amino-1-β-D-ribofuranosylimidazole-4-carboxamide is reacted with a reactive derivative of propionic acid, the resulting 5-amino-1-(2,3,5-tri-O-propionyl-β-D-ribofuranosyl)-imidazole-4-carboxamide is dehydrated, the resulting 5-amino-1-(2,3,5-tri-O-propionyl-β-D-ribofuranosyl)imidazole-4-carbonitrile is treated to remove the propionyls to yield 5-amino-1-β-D-ribofuranosylimidazole-4-carbonitrile and the last mentioned compound is reacted with phenylguanidine in the presence of aniline to produce N2 -phenyl-2,6-diaminonebularine.

Workup

  1. customto remove the propionyls

Sources & evidence

ORD record
ord-d4fc2cb4b5d740b7bba3310ce9944466
Source dataset
uspto-grants-1981_10
Patent number
US04293690

Reaction notes

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