Ammonia → 6-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purine

HRID 1876501Notes

Reaction equation

HRID 1876501 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.N>O.S(C1C=CC(C)=CC=1)(O)(=O)=O.C(OCC)(=O)C>[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

6

Reactant 3

HCID 222AmmoniaHCID 80803,4-dihydro-2H-pyranHCID 53592776-Chloropurine

Product 1

HCID 977406-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purineYield 91%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

Ethyl acetate (300 ml) was added to 6-chloropurine (25 g, 162 mmol) and tosylic acid monohydrate (460 mg, 2.43 mmol) and the resulting mixture was heated at 60° C. Dihydropyrane (16 ml, 178 mmol) was added and the resulting mixture was stirred at the same temperature for 30 minutes. The reaction mixture was cooled to room temperature followed by the addition of 28% aqueous ammonia solution (15 ml) and the organic layer was fractionated, washed with water, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure to give the title compound (35 g, 91%) as a pale yellow solid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-6a337bc726c74d719377d34b4ed87d5c
Source dataset
uspto-grants-2012_11
Patent number
US08309546B2

Reaction notes

Loading…