Potassium Carbonate → 2-{[1-Methyl-2-(methoxy)ethyl]oxy}-8-(methoxy)-9-(tetrahydro-2H-Pyran-4-ylmethyl)-9H-purin-6-amine

HRID 1011008Notes

Reaction equation

HRID 1011008 reaction equation
FC(F)(F)C(O)=O.[CH3:8][CH:9]([O:13][C:14]1[N:22]=[C:21]2[C:17]([N:18]=[C:19]([O:23][CH3:24])[NH:20]2)=[C:16]([NH2:25])[N:15]=1)[CH2:10][O:11][CH3:12].C(=O)([O-])[O-].[K+].[K+].CS(O[CH2:37][CH:38]1[CH2:43][CH2:42][O:41][CH2:40][CH2:39]1)(=O)=O>CN(C)C=O.C(OCC)(=O)C>[CH3:8][CH:9]([O:13][C:14]1[N:22]=[C:21]2[C:17]([N:18]=[C:19]([O:23][CH3:24])[N:20]2[CH2:37][CH:38]2[CH2:43][CH2:42][O:41][CH2:40][CH2:39]2)=[C:16]([NH2:25])[N:15]=1)[CH2:10][O:11][CH3:12]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 15166436Oxan-4-ylmethyl methanesulfonateHCID 178495541HCID 178495541, compound

Product 1

HCID 576998202-{[1-Methyl-2-(methoxy)ethyl]oxy}-8-(methoxy)-9-(tetrahydro-2H-Pyran-4-ylmethyl)-9H-purin-6-amineYield 54.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-{[1-methyl-2-(methoxy)ethyl]oxy}-8-(methoxy)-9H-purin-6-amine trifluoroacetic acid salt (500 mg) in dry N,N-dimethylformamide (4.5 ml) at room temperature and under nitrogen was added potassium carbonate (0.75 g) in one go. The reaction was stirred at 60° C. for 1.5 hours. Tetrahydro-2H-pyran-4-ylmethyl methanesulfonate (0.29 g) was added in one go and the reaction heated at 90° C. for 3 hours. The reaction was cooled to room temperature and then diluted with ethyl acetate (20 ml) and washed with water (15 ml). The organic layer was dried over magnesium sulphate, filtered and concentrated in vacuo. The product was purified by C18 reverse phase chromatography using water (containing 0.1% formic acid)-acetonitrile (containing 0.05% formic acid) as eluant (10-45%) to afford the title compound as a viscous clear oil (260 mg).

Workup

  1. temperaturethe reaction heated at 90° C. for 3 hours
  2. temperatureThe reaction was cooled to room temperature
  3. washwashed with water (15 ml)
  4. dry with materialThe organic layer was dried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe product was purified by C18 reverse phase chromatography

Sources & evidence

ORD record
ord-2f23697fef894d91a20ece1b0275d596
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

Loading…