Sodium Hydroxide → HCID 14886842, compound

HRID 893707Notes

Reaction equation

HRID 893707 reaction equation
C[Si]([C:5]#[C:6][C:7]1[N:11]([C@@H]2O[C@H](COC(=O)C)[C@@H](OC(=O)C)[C@H]2OC(=O)C)[CH:10]=[N:9][C:8]=1[C:30]#[N:31])(C)C.[OH-].[Na+]>Cl.CO>[C:6]([C:7]1[NH:11][CH:10]=[N:9][C:8]=1[C:30]#[N:31])#[CH:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 14803140HCID 14803140, compound

Product 1

HCID 14886842HCID 14886842, compoundYield 95.7%

Reagents, catalysts & solvents 1

HCID 21893726Hydrochloride methanolSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 447 mg (1 mmol) of 5-trimethylsilylethynyl-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl) imidazole-4-carbonitrile in a 1N hydrochloric acid-methanol (10 ml: 5 ml) solvent mixture was heated under reflux at 100° C. for 4 hours. After the reaction, the reaction solution was neutralized with 1N sodium hydroxide solution, silica gel powder was added, and the solvent was evaporated. The residue was adsorbed onto a silica gel column (2.7×13 cm), eluted with a 0-8% ethanol-chloroform solvent mixture, and crystallized from water-containing methanol to obtain 112 mg of pale yellow crystals of 5-ethynylimidazole-4-carbonitrile (yield: 95.7%).

Workup

  1. customAfter the reaction
  2. additionwas added
  3. customthe solvent was evaporated
  4. washeluted with a 0-8% ethanol-chloroform solvent mixture
  5. customcrystallized from water-
  6. additioncontaining methanol

Sources & evidence

ORD record
ord-8b77017d74a3495aa2c37a491f9409f5
Source dataset
uspto-grants-1992_06
Patent number
US05126361

Reaction notes

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