N,N-Dimethylaniline → Methanesulfonic acid--6-chloro-7H-purine (1/1)

HRID 1995739Notes

Reaction equation

HRID 1995739 reaction equation
[NH:1]1[C:9](=O)[C:8]2[NH:7][CH:6]=[N:5][C:4]=2[N:3]=[CH:2]1.CN(C)C1C=CC=CC=1.[CH3:20][S:21]([OH:24])(=[O:23])=[O:22].P(Cl)(Cl)([Cl:27])=O>>[CH3:20][S:21]([OH:24])(=[O:23])=[O:22].[Cl:27][C:9]1[N:1]=[CH:2][N:3]=[C:4]2[C:8]=1[NH:7][CH:6]=[N:5]2

Participants

5

Reactant 4

HCID 949N,N-DimethylanilineHCID 6395Methanesulfonic AcidHCID 24813Phosphorus oxychlorideHCID 135398638Hypoxanthine

Product 1

HCID 20487940Methanesulfonic acid--6-chloro-7H-purine (1/1)Yield 78%

Procedure

A mixture of 5 g (0.0368 mole) of hypoxanthine, 12.5 ml of N,N-dimethylaniline and 150 ml of phosphorus oxychloride was refluxed for 40 minutes. Excess phosphorus oxychloride was removed by vacuum distillation with an external oil bath having a temperature below 70° C. and 200 ml of methylene chloride were added to the oily residue. The red methylene chloride solution was cooled in an ice bath and 6 g (0.063 mole) of methanesulfonic acid were added slowly. The mixture was left in an ice bath with stirring for 1 hour and then filtered to give 7.20 g (78% yield) of 6-chloropurine methanesulfonate as a light yellow solid.

Workup

  1. temperaturewas refluxed for 40 minutes
  2. customExcess phosphorus oxychloride was removed by vacuum distillation with an external oil bath
  3. customa temperature below 70° C. and 200 ml of methylene chloride
  4. additionwere added to the oily residue
  5. temperatureThe red methylene chloride solution was cooled in an ice bath
  6. waitThe mixture was left in an ice bath
  7. filtrationfiltered

Sources & evidence

ORD record
ord-35d3f4882f68414c86f7241694b2faad
Source dataset
uspto-grants-1983_09
Patent number
US04405781

Reaction notes

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