Ammonia → 5-amino-1-beta-D-ribofuranosyl-4-cyanoimidazole
Reaction equation
[NH2:1][C:2]1[N:6]([C@@H:7]2[O:21][C@H:20]([CH2:22][O:23]C(=O)CC)[C@@H:14]([O:15]C(=O)CC)[C@H:8]2[O:9]C(=O)CC)[CH:5]=[N:4][C:3]=1[C:28]#[N:29].N>>[NH2:1][C:2]1[N:6]([C@@H:7]2[O:21][C@H:20]([CH2:22][OH:23])[C@@H:14]([OH:15])[C@H:8]2[OH:9])[CH:5]=[N:4][C:3]=1[C:28]#[N:29]Participants
Procedure
A method for producing N2 -phenyl-2,6-diaminonebularine, which comprises reacting 5-amino-1-β-D-ribofuranosylimidazole-4-carboxamide with a reactive derivative of propionic acid to yield 5-amino-1-(2,3,5,-tri-O-propionyl-β-D-ribofuranosyl)imidazole-4-carboxamide, dehydrating 5-amino-1-(2,3,5-tri-O-propionyl-β-D-ribofuranosyl)imidazole-4-carboxamide to yield 5-amino-4-cyano-1-(2,3,5-tri-O-propionyl-β-D-ribofuranosyl)imidazole, treating 5-amino-4-cyano-1-(2,3,5-tri-O-propionyl-β-D-ribofuranosyl)imidazole with aqueous ammonia or alkali metal alkoxide to yield 5-amino-1-β-D-ribofuranosyl-4-cyanoimidazole and reacting 5-amino-1-β-D-ribofuranosyl-4-cyanoimidazole with phenylcyanamide in the presence of ammonia to yield N2 -phenyl-2,6-diaminonebularine.
Sources & evidence
- ORD record
- ord-3f5ef881421b4ec59715c6b64da7ee3b
- Source dataset
- uspto-grants-1981_03
- Patent number
- US04255565
Reaction notes
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