p-Toluenesulfonic acid monohydrate → 9H-Purine, 6-iodo-9-(tetrahydro-2H-pyran-2-yl)-

HRID 1042284Notes

Reaction equation

HRID 1042284 reaction equation
[I:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][NH:6]2.[OH2:11].[C:12]1(C)C=[CH:16][C:15](S(O)(=O)=O)=[CH:14][CH:13]=1>CCOC(C)=O>[I:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH:16]1[CH2:15][CH2:14][CH2:13][CH2:12][O:11]1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 178506563HCID 178506563, compound

Product 1

HCID 2340049H-Purine, 6-iodo-9-(tetrahydro-2H-pyran-2-yl)-

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

In a RB flask were placed 6-iodo-9H-purine (2680 mg, 10894 μmol), 3,4-dihydro-2(H)-pyran (2982 μl, 32682 μmol), and p-toluenesulfonic acid monohydrate (34.0 mg, 218 μmol) in EtOAc (150 mL) and heated to reflux for 2 hours. After cooling to RT, the reaction mixture was washed with NaHCO3 (aq., sat., 100 mL), then brine (100 mL). The organic solution was concentrated in vacuo. The residue was redissolved in a small amount of DCM and then put on a layer of silica gel in a funnel. The silica was rinsed with EtOAc/hexane (1:1). A light yellow solution (filtrate) was collected and concentrated to give a waxy product. This product was treated with hexanes to give the titled compound as an off white solid. MS Found: (ESI pos. ion) m/z 331 (M+H+).

Workup

  1. customIn a RB flask were placed
  2. temperatureto reflux for 2 hours
  3. washthe reaction mixture was washed with NaHCO3 (aq., sat., 100 mL)
  4. concentrationThe organic solution was concentrated in vacuo
  5. dissolutionThe residue was redissolved in a small amount of DCM
  6. customput on a layer of silica gel in a funnel
  7. washThe silica was rinsed with EtOAc/hexane (1:1)
  8. customA light yellow solution (filtrate) was collected
  9. concentrationconcentrated
  10. customto give a waxy product

Sources & evidence

ORD record
ord-ee8e74193032432c81ef015a7f8d9938
Source dataset
uspto-grants-2013_10
Patent number
US08557830B2

Reaction notes

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