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

HRID 1493550Notes

Reaction equation

HRID 1493550 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+]>O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[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

5

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%

Reagents, catalysts & solvents 1

HCID 521998p-Toluenesulfonic acid monohydrateCatalyst

Procedure

To a warmed (60° C.) slurry of 6-chloropurine (20 g, 0.1294 mol) and p-toluenesulfonic acid monohydrate (0.35 g), dihydropyran (13.4 mL, 0.172 mol) was added with stirring over a period of 30 min. After an additional 30 min of heating, the mixture was allowed to cool to room temperature for 1 h. Concentrated ammonium hydroxide (12 mL) was added and stirring was continued for 5 min. 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 (78%), mp 70°-71° C.

Workup

  1. additionwas added
  2. temperatureAfter an additional 30 min of heating
  3. stirringstirring
  4. waitwas continued for 5 min
  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-35c395e2bb3e4352b7eb259bfe2754ce
Source dataset
uspto-grants-1991_06
Patent number
US05021574

Reaction notes

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