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

HRID 1396583Notes

Reaction equation

HRID 1396583 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.CC1C=CC(S(O)(=O)=O)=CC=1.[O:22]1[CH:27]=[CH:26][CH2:25][CH2:24][CH2:23]1.C([O-])([O-])=O.[Na+].[Na+]>C(OCC)(=O)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:23]1[CH2:24][CH2:25][CH2:26][CH2:27][O:22]1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 10340Sodium CarbonateHCID 178478393HCID 178478393, compound

Product 1

HCID 977406-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6-chloro-9H-purine (A-1) (1.29 mol, 1 eq) and anhydrous TsOH (0.02 mol, 0.015 eq) in ethyl acetate (1000 mL), 3,4-dihydro-2H-pyran (1.94 mol, 1.5 eq) is added and the resulting mixture is stirred at reflux for 2 h. The reaction mixture is allowed to cool to RT, aqueous Na2CO3 solution (3%, 500 mL) is added and the resulting mixture is stirred for 10 min. The organic layer is separated, washed with water (2×500 mL) and brine (500 mL), dried over anhydrous Na2SO4, and filtered. The filtrate is concentrated in vacuo. The product is dissolved in ethyl acetate (50 mL), and then n-heptane (500 mL) is added. The resulting mixture is stirred at RT for 1 h. The precipitate is collected by filtration, rinsed with heptane (100 mL) and dried in vacuo to afford the product, 6-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purine (A-2).

Workup

  1. temperatureat reflux for 2 h
  2. stirringthe resulting mixture is stirred for 10 min
  3. customThe organic layer is separated
  4. washwashed with water (2×500 mL) and brine (500 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationThe filtrate is concentrated in vacuo
  8. dissolutionThe product is dissolved in ethyl acetate (50 mL)
  9. additionn-heptane (500 mL) is added
  10. stirringThe resulting mixture is stirred at RT for 1 h
  11. filtrationThe precipitate is collected by filtration
  12. washrinsed with heptane (100 mL)
  13. customdried in vacuo

Sources & evidence

ORD record
ord-bc03c4a014c741faab4a33eb3e37fa09
Source dataset
uspto-grants-2014_12
Patent number
US08901133B2

Reaction notes

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