3,4-dihydro-2H-pyran → 6-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purine

HRID 1655855Notes

Reaction equation

HRID 1655855 reaction equation
[Cl: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.[OH-].[NH4+]>>[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:12]1[CH2:13][CH2:14][CH2:15][CH2:16][O:11]1

Participants

4

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 14923Ammonium HydroxideHCID 53592776-Chloropurine

Product 1

HCID 977406-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purineYield 93.9%

Procedure

To a warmed (60° C.) slurry of 6-chloropurine (20 g, 0.1294 mol) and R-toluenesulfonic acid monohydrate (0.35 g), dihydropyran (13.4 mL, 0.172 mol) was added with stirring over a period of 30 minutes. After an additional 30 minutes of heating, the mixture was allowed to cool to room temperature for 1 hour. Concentrated ammonium hydroxide (12 mL) was added and stirring was continued for 5 minutes. The solution was washed with water (4×70 mL) and the organic layer was dried (Na2SO4), filtered and concentrated in vacuo to give a syrup (about 29 g) which slowly crystallized upon standing. Extraction with boiling hexane gave the product as a solid, 24.36 g in two crops (784), mp 70°-71° C.

Workup

  1. additionwas added
  2. temperatureAfter an additional 30 minutes of heating
  3. stirringstirring
  4. waitwas continued for 5 minutes
  5. washThe solution was washed with water (4×70 mL)
  6. dry with materialthe organic layer was dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ede026d4509948c398ed46df087d4ee9
Source dataset
uspto-grants-1993_10
Patent number
US05252569

Reaction notes

Loading…