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

HRID 1880028Notes

Reaction equation

HRID 1880028 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-ab64e02a20f64394a943ce686bb10aac
Source dataset
uspto-grants-2012_11
Patent number
US08318718B2

Reaction notes

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