Potassium Carbonate → 8-(Methoxy)-2-[(tetrahydro-2-furanylmethyl)oxy]-9-(tetrahydro-2H-Pyran-4-ylmethyl)-9H-purin-6-amine

HRID 1011033Notes

Reaction equation

HRID 1011033 reaction equation
FC(F)(F)C(O)=O.[CH3:8][O:9][C:10]1[NH:11][C:12]2[C:17]([N:18]=1)=[C:16]([NH2:19])[N:15]=[C:14]([O:20][CH2:21][CH:22]1[CH2:26][CH2:25][CH2:24][O:23]1)[N:13]=2.C(=O)([O-])[O-].[K+].[K+].CS(O[CH2:38][CH:39]1[CH2:44][CH2:43][O:42][CH2:41][CH2:40]1)(=O)=O>CN(C=O)C>[CH3:8][O:9][C:10]1[N:11]([CH2:38][CH:39]2[CH2:44][CH2:43][O:42][CH2:41][CH2:40]2)[C:12]2[C:17]([N:18]=1)=[C:16]([NH2:19])[N:15]=[C:14]([O:20][CH2:21][CH:22]1[CH2:26][CH2:25][CH2:24][O:23]1)[N:13]=2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 15166436Oxan-4-ylmethyl methanesulfonateHCID 178493992HCID 178493992, compound

Product 1

HCID 576996338-(Methoxy)-2-[(tetrahydro-2-furanylmethyl)oxy]-9-(tetrahydro-2H-Pyran-4-ylmethyl)-9H-purin-6-amineYield 54.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

8-(Methoxy)-2-[(tetrahydro-2-furanylmethyl)oxy]-9H-purin-6-amine trifluoroacetate salt (0.30 g) was dissolved in dry DMF (5 mL). To this solution was added anhydrous potassium carbonate (0.4376 g) and then the reaction mixture was heated to 60° C. under nitrogen for 1 hour. The reaction mixture was then cooled to room temperature before adding tetrahydro-2H-pyran-4-ylmethyl methanesulfonate (0.1690 g) and then the resultant reaction mixture was heated to 90° C. for 2.5 hours. The reaction mixture was cooled and then quenched with water (50 mL), followed by extraction into ethyl acetate (50 mL, 3 times). After separating, the organic layers were combined and dried by passing through a hydrophobic frit. Evaporation under reduced pressure gave mobile oil which was then purified by C18 reverse phase chromatography using water (containing 0.1% formic acid)-acetonitrile (containing 0.05% formic acid) as eluent (10-45%). This gave the title compound as a white solid (0.1560 g).

Workup

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. customthe resultant reaction mixture
  3. temperaturewas heated to 90° C. for 2.5 hours
  4. temperatureThe reaction mixture was cooled
  5. customquenched with water (50 mL)
  6. extractionfollowed by extraction into ethyl acetate (50 mL, 3 times)
  7. customAfter separating
  8. customdried
  9. customEvaporation under reduced pressure
  10. customgave mobile oil which
  11. customwas then purified by C18 reverse phase chromatography

Sources & evidence

ORD record
ord-467e74118f194d50af7659e42162595c
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

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