3,4-dihydro-2H-pyran → 6-Bromo-9-(tetrahydro-2H-pyran-2-YL)-9H-purine

HRID 410162Notes

Reaction equation

HRID 410162 reaction equation
[Br:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[NH:4][CH:5]=[N:6]2.[O:11]1[CH:16]=[CH:15][CH2:14][CH2:13][CH2:12]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CCOC(C)=O>[Br:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16][O:11]1

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 521998p-Toluenesulfonic acid monohydrateHCID 5287830Purine, 6-bromo-

Product 1

HCID 583686166-Bromo-9-(tetrahydro-2H-pyran-2-YL)-9H-purine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 6-bromopurine (2.0 g, 10 mmol), 3,4-dihydro-2h-pyran (1.0 ml, 11 mmol), and p-toluenesulfonic acid monohydrate (0.050 g, 0.26 mmol) in EtOAc (30 mL) was stirred at reflux under a reflux condenser for 48 h. The reaction mixture (suspension) was allowed to cool to room temperature and the solid was removed by suction filtration and washed with EtOAc (50 mL). The combined wash was concentrated in vacuo to afford 2.1 g as oil. The oil was chromatographed through a Redi-Sep® pre-packed silica gel column, eluting with a gradient of 30% to 60% EtOAc in hexane, to provide product.

Workup

  1. temperatureat reflux under a reflux condenser for 48 h
  2. customthe solid was removed by suction filtration
  3. washwashed with EtOAc (50 mL)
  4. washThe combined wash
  5. concentrationwas concentrated in vacuo
  6. customto afford 2.1 g as oil
  7. customThe oil was chromatographed through a Redi-Sep® pre-packed silica gel column
  8. washeluting with a gradient of 30% to 60% EtOAc in hexane
  9. customto provide product

Sources & evidence

ORD record
ord-1bc1870b1aa743c6aa37a583f894f1ff
Source dataset
uspto-grants-2014_06
Patent number
US08759532B2

Reaction notes

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