p-Toluenesulfonic acid → 6-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purine

HRID 1505489Notes

Reaction equation

HRID 1505489 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][NH:6]2.[CH3:11][C:12]1C=C[C:15](S(O)(=O)=O)=[CH:14][CH:13]=1.C([O:24]C(=O)C)C>>[Cl:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH:15]1[CH2:14][CH2:13][CH2:12][CH2:11][O:24]1

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 8857Ethyl AcetateHCID 178478393HCID 178478393, compound

Product 1

HCID 977406-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purineYield 97%

Procedure

6-chloro-9H-purine (500 mg, 3.2 mmol), 4-methyl benzene sulfonic acid (12 mg, 0.07 mmol), and 3,4-dehydro-2H-pyran (0.9 mL, 9.7 mmol) were added into ethylacetate solvent and stirred. The reactant was stirred at 90° C. for approximately 1 hour until the solid is dissolved completely. After concentrating the solvent, the residuals were refined by means of column chromatography, so that 749 mg of the target compound, 6-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purine (percentage yield: 97%), was obtained.

Workup

  1. stirringThe reactant was stirred at 90° C. for approximately 1 hour until the solid
  2. dissolutionis dissolved completely
  3. concentrationAfter concentrating the solvent

Sources & evidence

ORD record
ord-71546921277b40b192963d555fe30af6
Source dataset
uspto-grants-2015_12
Patent number
US09216981B2

Reaction notes

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