1-(beta-D-ribofuranosyl)-5-(thiocarbamoyl)amino-1H-imidazole-4-carboxamide → Guanosine

HRID 1588947Notes

Reaction equation

HRID 1588947 reaction equation
[C@@H:1]1([N:10]2[C:14]([NH:15][C:16](=S)[NH2:17])=[C:13]([C:19]([NH2:21])=[O:20])[N:12]=[CH:11]2)[O:7][C@H:6]([CH2:8][OH:9])[C@@H:4]([OH:5])[C@H:2]1[OH:3]>[OH-].[Na+].S([O-])([O-])(=O)=O.[Cu+2]>[C@@H:1]1([N:10]2[CH:11]=[N:12][C:13]3[C:19](=[O:20])[NH:21][C:16]([NH2:17])=[N:15][C:14]2=3)[O:7][C@H:6]([CH2:8][OH:9])[C@@H:4]([OH:5])[C@H:2]1[OH:3]

Participants

4

Reactant 1

HCID 537754951-(beta-D-ribofuranosyl)-5-(thiocarbamoyl)amino-1H-imidazole-4-carboxamide

Product 1

HCID 135398635GuanosineYield 65%

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 14798Sodium HydroxideSolvent

Procedure

The crude product of 1-(β-D-ribofuranosyl)-5-(thiocarbamoyl)amino-1H-imidazole-4-carboxamide (5.0 g) was added to a suspension of copper sulphate (2.9 g, 18 mM) in 3N sodium hydroxide (60 ml) and refluxed for 1 hour. After filtration 33% aqueous acetic acid (30 ml) was added to the filtrate and it was refluxed again while being treated with activated coal. The coal was filtered off, and the solution was cooled to room temperature overnight. Filtration, washing with water and drying gave 2.0 g (65%) of 9-β-D-ribofuranosyl guanine, H2O (guanosine, H2O) as a white powder, mp. 250° C. (dec.). The product had the same physical data as an authentic sample of guanosine, H2O.

Workup

  1. temperaturerefluxed for 1 hour
  2. filtrationAfter filtration 33% aqueous acetic acid (30 ml)
  3. additionwas added to the filtrate and it
  4. temperaturewas refluxed again
  5. additionwhile being treated with activated coal
  6. filtrationThe coal was filtered off
  7. filtrationFiltration
  8. washwashing with water
  9. customdrying

Sources & evidence

ORD record
ord-c554eee1db7143e9bfd0c1a4aebf75c1
Source dataset
uspto-grants-1993_06
Patent number
US05223619

Reaction notes

Loading…