Water → 2-Butoxy-8-methoxy-9-[2-(tetrahydrofuran-2-yl)ethyl]-9H-Purin-6-amine

HRID 1010937Notes

Reaction equation

HRID 1010937 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([O:12][C:13]1[NH:14][C:15]([NH2:24])=[C:16]2[C:20]([N:21]=1)=[N:19][C:18]([O:22][CH3:23])=[N:17]2)[CH2:9][CH2:10][CH3:11].C(=O)([O-])[O-].[K+].[K+].Br[CH2:32][CH2:33][CH:34]1[CH2:38][CH2:37][CH2:36][O:35]1.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[CH2:32][CH2:33][CH:34]2[CH2:38][CH2:37][CH2:36][O:35]2)=[C:15]([NH2:24])[N:14]=1)[CH2:9][CH2:10][CH3:11]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 536918712-(2-Bromoethyl)oxolaneHCID 178450357HCID 178450357, compound

Product 1

HCID 576996172-Butoxy-8-methoxy-9-[2-(tetrahydrofuran-2-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-1H-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-(2-Bromoethyl)tetrahydrofuran (122 mg) was added and the stirring mixture heated at 50° C. for 4 h. After allowing to cool, 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 (containing 0.1% formic acid)-acetonitrile (containing 0.05% formic acid) as eluent (20-60%) 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 clear oil, yield 122 mg).

Workup

  1. temperaturewas heated
  2. temperaturethe stirring mixture heated at 50° C. for 4 h
  3. temperatureto cool
  4. extractionthe mixture extracted three times with ethyl acetate
  5. washThe combined extracts were washed with water
  6. dry with materialbrine, dried
  7. customby passing through a phase separation cartridge
  8. customto give a brown oil
  9. customThis was purified by C18 reverse phase chromatography
  10. customevaporated
  11. customto remove acetonitrile
  12. extractionextracted three times with dichloromethane
  13. customthe combined extracts dried
  14. customby passing through a phase separation cartridge
  15. customthen evaporated

Sources & evidence

ORD record
ord-327cbe66d29c49589e97d4c2fb04aa2f
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

Loading…