Water → N2-Butyl-8-methoxy-9-[2-(tetrahydro-2H-pyran-3-yl)ethyl]-9H-purine-2,6-diamine

HRID 1010943Notes

Reaction equation

HRID 1010943 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([NH: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]([NH: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 178448879HCID 178448879, compound

Product 1

HCID 57699758N2-Butyl-8-methoxy-9-[2-(tetrahydro-2H-pyran-3-yl)ethyl]-9H-purine-2,6-diamine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A stirring mixture of N2-butyl-8-methoxy-9H-purine-2,6-diamine trifluoroacetic acid 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 (20-60%) 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 brown solid, yield 138 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-37107d3f0b5144e8b5900a43d2a7a0d5
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

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