Sodium → HCID 12799424, compound

HRID 1447003Notes

Reaction equation

HRID 1447003 reaction equation
C([O:4][C@H:5]1[C@H:9]([O:10]C(=O)C)[C@@H:8]([CH2:14][O:15]C(=O)C)[O:7][C@H:6]1[N:19]1[C:27]2[CH:26]=[CH:25][NH:24][C:23](=[S:28])[C:22]=2[N:21]=[CH:20]1)(=O)C.[Na]>CO>[C@@H:6]1([N:19]2[C:27]3[CH:26]=[CH:25][NH:24][C:23](=[S:28])[C:22]=3[N:21]=[CH:20]2)[O:7][C@H:8]([CH2:14][OH:15])[C@@H:9]([OH:10])[C@@H:5]1[OH:4]

Participants

4

Reactant 2

HCID 5360545SodiumHCID 54313119HCID 54313119, compound

Product 1

HCID 12799424HCID 12799424, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 5.0 g of 1-(2,3,5-tri-O-acetyl-β-D-arabinofuranosyl)-1,5-dihydro-4H-imidazo[4,5-c]pyridine-4-thione, 200 ml of methanol, and 54 mg of sodium metholate is heated under reflux for 2 hours and treated with IRC-50 ion exchange resin. The filtrate is evaporated in vacuo and the resulting residue is recrystallized from ethanol-water to provide 1-β-D-arabinofuranosyl-1,5-dihydro-4H-imidazo[4,5-c]pyridine-4-thione.

Workup

  1. temperatureunder reflux for 2 hours
  2. additiontreated with IRC-50 ion exchange resin
  3. customThe filtrate is evaporated in vacuo
  4. customthe resulting residue is recrystallized from ethanol-water

Sources & evidence

ORD record
ord-3fb12c6ff215420286a221974d691cc6
Source dataset
uspto-grants-1982_02
Patent number
US04315000

Reaction notes

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