Sodium hydride → HCID 178476353, compound

HRID 597476Notes

Reaction equation

HRID 597476 reaction equation
[C:1]([O:4][C@@H:5]1[C@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@@H:8]([CH2:14][O:15][C:16](=[O:18])[CH3:17])[O:7][C@H:6]1[N:19]1[CH:27]=[N:26][C:25]2[CH:24]([CH2:28][OH:29])[NH:23][CH:22]=[N:21][C:20]1=2)(=[O:3])[CH3:2].[H-].[Na+].[S:32](Cl)([CH3:35])(=[O:34])=[O:33].O.C(Cl)(Cl)Cl>C(COC)OC>[C:1]([O:4][C@@H:5]1[C@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@@H:8]([CH2:14][O:15][C:16](=[O:18])[CH3:17])[O:7][C@H:6]1[N:19]1[CH:27]=[N:26][C:25]2[CH:24]([CH2:28][O:29][S:32]([CH3:35])(=[O:34])=[O:33])[NH:23][CH:22]=[N:21][C:20]1=2)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 31297Methanesulfonyl chlorideHCID 22418719Chloroform waterHCID 178476352HCID 178476352, compound

Product 1

HCID 178476353HCID 178476353, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

9-(2,3,5-Tri-O-acetyl-β-D-ribofuranosyl)-6-hydroxymethyl-1,6-dihydropurine (VI) (217 mg.) obtained in (2) was dissolved in purified anhydrous dimethoxyethane (10 ml.) and cooled to -10° to -15° C. To the cooled solution were added sodium hydride (76 mg., 3 moles) and mesyl chloride (180 mg., 3 moles), successively. The reaction was conducted at 0° - 5° C. for 17 hours. The reaction mixture was then treated with water-chloroform and the chloroform layer thus separated was washed with 0.5% aqueous sodium hydrogen carbonate, then with water, dried over anhydrous sodium sulfate and concentrated to yield II as a pale-yellow oil (235 mg., yield: 91%). This substance is unstable and decomposes in chloroform within 2-3 hours.

Workup

  1. temperaturecooled to -10° to -15° C
  2. customthe chloroform layer thus separated
  3. washwas washed with 0.5% aqueous sodium hydrogen carbonate
  4. dry with materialwith water, dried over anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-99b47f7c627e4676b195eeb84d9bd1be
Source dataset
uspto-grants-1977_03
Patent number
US04014769

Reaction notes

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