Potassium Carbonate → 8-(Methoxy)-2-{[2-(methoxy)ethyl]oxy}-9-(tetrahydro-3-furanylmethyl)-9H-purin-6-amine

HRID 1011028Notes

Reaction equation

HRID 1011028 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][CH2:22][O:23][CH3:24])[N:13]=2.C(=O)([O-])[O-].[K+].[K+].CS(O[CH2:36][CH:37]1[CH2:41][CH2:40][O:39][CH2:38]1)(=O)=O>CN(C=O)C>[CH3:8][O:9][C:10]1[N:11]([CH2:36][CH:37]2[CH2:41][CH2:40][O:39][CH2:38]2)[C:12]2[C:17]([N:18]=1)=[C:16]([NH2:19])[N:15]=[C:14]([O:20][CH2:21][CH2:22][O:23][CH3:24])[N:13]=2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 22273010(Tetrahydrofuran-3-yl)methyl methanesulfonateHCID 178496185HCID 178496185, compound

Product 1

HCID 576996808-(Methoxy)-2-{[2-(methoxy)ethyl]oxy}-9-(tetrahydro-3-furanylmethyl)-9H-purin-6-amineYield 44.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

8-(Methoxy)-2-{[2-(methoxy)ethyl]oxy}-9H-purin-6-amine trifluoroacetate salt (0.30 g) was dissolved in dry DMF (5 mL). To this was added anhydrous potassium carbonate (0.47 g) and then heated to 60° C. for 1.5 hours. The reaction mixture was cooled to room temperature and tetrahydro-3-furanylmethyl methanesulfonate (0.168 g) was added. The reaction mixture was then heated to 90° C. for 3.5 hours. The reaction mixture was then quenched into water (100 mL) and extracted into ethyl acetate (50 mL, 3 times). The organic was separated and dried by passing through a hydrophobic frit and then evaporated under reduced pressure to give a glassy solid. This was 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 (0.1233 g).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. temperatureThe reaction mixture was then heated to 90° C. for 3.5 hours
  3. customThe reaction mixture was then quenched into water (100 mL)
  4. extractionextracted into ethyl acetate (50 mL, 3 times)
  5. customThe organic was separated
  6. customdried
  7. customevaporated under reduced pressure
  8. customto give a glassy solid
  9. customThis was purified by C18 reverse phase chromatography

Sources & evidence

ORD record
ord-94098a0c3d2040cd8a53718ff67d7414
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

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