Water → 2-Butoxy-8-methoxy-9-[2-(tetrahydro-2H-pyran-3-yl)ethyl]-9H-purin-6-amine

HRID 1010942Notes

Reaction equation

HRID 1010942 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([O:12][C:13]1[N:21]=[C:20]2[C:16]([N:17]=[C:18]([O:22][CH3:23])[NH:19]2)=[C:15]([NH2:24])[N:14]=1)[CH2:9][CH2:10][CH3:11].C(=O)([O-])[O-].[K+].[K+].CS(O[CH2:36][CH2:37][CH:38]1[CH2:43][CH2:42][CH2:41][O:40][CH2:39]1)(=O)=O.O>CN(C)C=O>[CH2:8]([O:12][C:13]1[N:21]=[C:20]2[C:16]([N:17]=[C:18]([O:22][CH3:23])[N:19]2[CH2:36][CH2:37][CH:38]2[CH2:43][CH2:42][CH2:41][O:40][CH2:39]2)=[C:15]([NH2:24])[N:14]=1)[CH2:9][CH2:10][CH3:11]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 576996182-(Tetrahydro-2H-pyran-3-yl)ethyl methanesulfonateHCID 178450370HCID 178450370, compound

Product 1

HCID 576997412-Butoxy-8-methoxy-9-[2-(tetrahydro-2H-pyran-3-yl)ethyl]-9H-purin-6-amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A stirring mixture of 2-butoxy-8-methoxy-9H-purin-6-amine trifluoroacetate salt (200 mg) and potassium carbonate (236 mg) in dry N,N-dimethylformamide (2 ml) was heated with stirring at 60° C. for 1 h. 2-(Tetrahydro-2H-pyran-3-yl)ethyl methanesulfonate (142 mg) was added and the stirring mixture heated at 60° C. for 3 h. Water was added and the mixture extracted three times with ethyl acetate. The combined extracts were washed with water then brine, dried by passing through a phase separation cartridge and stripped to give a brown oil. This was purified by C18 reverse phase chromatography using water (0.1% formic acid)-acetonitrile (0.05% formic acid) as eluent (20-70%) and the appropriate fractions combined and evaporated to remove acetonitrile. The remaining aqueous mixture was made basic with saturated sodium hydrogen carbonate, extracted three times with dichloromethane and the combined extracts dried by passing through a phase separation cartridge then evaporated to afford the title compound as a brown oil, yield 108 mg.

Workup

  1. temperaturewas heated
  2. temperaturethe stirring mixture heated at 60° C. for 3 h
  3. extractionthe mixture extracted three times with ethyl acetate
  4. washThe combined extracts were washed with water
  5. dry with materialbrine, dried
  6. customby passing through a phase separation cartridge
  7. customto give a brown oil
  8. customThis was purified by C18 reverse phase chromatography
  9. customevaporated
  10. customto remove acetonitrile
  11. extractionextracted three times with dichloromethane
  12. customthe combined extracts dried
  13. customby passing through a phase separation cartridge
  14. customthen evaporated

Sources & evidence

ORD record
ord-79bbf318e53044e8b539413e4db3b77f
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

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