Sodium Carbonate → HCID 53958625, compound

HRID 1110844Notes

Reaction equation

HRID 1110844 reaction equation
[NH2:1][C:2]1[N:6]([C@@H:7]2[O:19][C@H:18]([CH2:20][O:21][C:22](=[O:24])[CH3:23])[C@@H:13]([O:14][C:15](=[O:17])[CH3:16])[C@H:8]2[O:9][C:10](=[O:12])[CH3:11])[CH:5]=[N:4][C:3]=1[C:25]#[N:26].[CH3:27][C:28]([N:30]([CH3:32])[CH3:31])=O.P(Cl)(Cl)(Cl)=O.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[CH3:31][N:30]([CH3:32])[C:28](=[N:1][C:2]1[N:6]([C@@H:7]2[O:19][C@H:18]([CH2:20][O:21][C:22](=[O:24])[CH3:23])[C@@H:13]([O:14][C:15](=[O:17])[CH3:16])[C@H:8]2[O:9][C:10](=[O:12])[CH3:11])[CH:5]=[N:4][C:3]=1[C:25]#[N:26])[CH3:27]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 31374DimethylacetamideHCID 13830071HCID 13830071, compound

Product 1

HCID 53958625HCID 53958625, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 0.73 g of 5-amino-4-cyano-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-imidazole, prepared as described by Suzuki and Kumashiro, Chem. Abstracts 71, 12561n (1969), and dimethylacetamide (0.70 g) in acetonitrile (5 ml) is added dropwise phosphoryl chloride (0.61 g) and the mixture is stirred under nitrogen for 20 hours at room temperature. The mixture is poured into 5% aqueous sodium carbonate and extracted with ethyl acetate and the organic layer washed with saturated sodium chloride solution and dried over sodium sulfate. The organic extract is concentrated to dryness at reduced pressure to afford 5-[1-(dimethylamino)-ethylideneamino]-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-imidazole-4-carbonitrile as an oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washthe organic layer washed with saturated sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. extractionThe organic extract
  5. concentrationis concentrated to dryness at reduced pressure

Sources & evidence

ORD record
ord-ab8f66c24d7b44cd858799a5e558abeb
Source dataset
uspto-grants-1990_12
Patent number
US04977144

Reaction notes

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