Dimethylformamide → 6-Chloropurine riboside

HRID 636322Notes

Reaction equation

HRID 636322 reaction equation
C([C@@:4]1([OH:28])[C@:8](C(=O)C)([OH:9])[C@@H:7]([CH2:13][O:14]C(=O)C)[O:6][C@H:5]1[N:18]1[C:27]2[N:26]=[CH:25][N:24]=[C:22](O)[C:21]=2[N:20]=[CH:19]1)(=O)C.S(Cl)([Cl:31])=O.CN(C)C=O>C(Cl)(Cl)Cl>[Cl:31][C:22]1[N:24]=[CH:25][N:26]=[C:27]2[C:21]=1[N:20]=[CH:19][N:18]2[C@@H:5]1[O:6][C@H:7]([CH2:13][OH:14])[C@@H:8]([OH:9])[C@H:4]1[OH:28]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 178476358HCID 178476358, compound

Product 1

HCID 930036-Chloropurine ribosideYield 60%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

50 g of 2′,3′,5′-O-triacetylinosine was dissolved in 400 ml of chloroform. 30 ml of thionyl chloride and 7.2 ml of dimethylformamide were added, and the solution was refluxed with heating for 2 to 4 hours. The reaction mixture was poured into ice cold water, and the separated chloroform layer was washed with saturated aqueous solution of sodium hydrogencarbonate and brine. After drying over sodium sulfate anhydride, the solvent was distilled off. The residue was dissolved in 20% ammonia methanol solution and the container was sealed. After stirring for 3 to 5 hours, the solution was concentrated under reduced pressure. The precipitated crystalline was separated by filtration and dried to give 6-chloro-9-β-D-ribofuranosyl-9H-purine (yield: 60%).

Workup

  1. temperaturethe solution was refluxed
  2. temperaturewith heating for 2 to 4 hours
  3. additionThe reaction mixture was poured into ice cold water
  4. washthe separated chloroform layer was washed with saturated aqueous solution of sodium hydrogencarbonate and brine
  5. dry with materialAfter drying over sodium sulfate anhydride
  6. distillationthe solvent was distilled off
  7. dissolutionThe residue was dissolved in 20% ammonia methanol solution
  8. customthe container was sealed
  9. concentrationthe solution was concentrated under reduced pressure
  10. customThe precipitated crystalline was separated by filtration
  11. customdried

Sources & evidence

ORD record
ord-85313e7e46f24025915cb64735485258
Source dataset
uspto-grants-2001_02
Patent number
USRE037077E1

Reaction notes

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