Ammonia → HCID 15086922, compound

HRID 1110843Notes

Reaction equation

HRID 1110843 reaction equation
[CH3:1][N:2]([CH3:31])[C:3](=[N:5][C:6]1[N:10]([C@@H:11]2[O:23][C@H:22]([CH2:24][O:25]C(=O)C)[C@@H:17]([O:18]C(=O)C)[C@H:12]2[O:13]C(=O)C)[CH:9]=[N:8][C:7]=1[C:29]#[N:30])[CH3:4].[H-].[Na+].N>O1CCOCC1>[NH2:30][C:29]1[CH:4]=[C:3]([N:2]([CH3:31])[CH3:1])[N:5]=[C:6]2[N:10]([C@@H:11]3[O:23][C@H:22]([CH2:24][OH:25])[C@@H:17]([OH:18])[C@H:12]3[OH:13])[CH:9]=[N:8][C:7]=12

Participants

5

Reactant 3

HCID 222AmmoniaHCID 24758Sodium hydrideHCID 53958625HCID 53958625, compound

Product 1

HCID 15086922HCID 15086922, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

5-[1-(dimethylamino)-ethylideneamino]-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-imidazole-4-carbonitrile is reacted with sodium hydride in dioxane as described in Example 10 and the crude product is reacted with methanolic ammonia at room temperature over 18 hours. The mixture is concentrated to dryness and purified by silica gel chromatography to afford 7-amino-3-β-D-ribofuranosyl-N,N-dimethyl-3H-imidazo[4,5-b]pyridine-5-amine.

Workup

  1. concentrationThe mixture is concentrated to dryness
  2. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-b27ef133ee4741e282039071d08aefec
Source dataset
uspto-grants-1990_12
Patent number
US04977144

Reaction notes

Loading…