Potassium Carbonate → 2-Butyloxy-8-methoxy-9-[2-(tetrahydro-3-furanyl)ethyl]-9H-Purin-6-amine

HRID 1010991Notes

Reaction equation

HRID 1010991 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+].Br[CH2:32][CH2:33][CH:34]1[CH2:38][CH2:37][O:36][CH2:35]1>CN(C=O)C>[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][O:36][CH2:35]2)=[C:15]([NH2:24])[N:14]=1)[CH2:9][CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 510003433-(2-Bromoethyl)oxolaneHCID 178450370HCID 178450370, compound

Product 1

HCID 576997902-Butyloxy-8-methoxy-9-[2-(tetrahydro-3-furanyl)ethyl]-9H-Purin-6-amineYield 138.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2-butoxy-8-methoxy-9H-purin-6-amine trifluoroacetate salt (200 mg) and potassium carbonate (236 mg) in dry DMF (2 mL) was heated at 60° C. with stirring for 1 h. 3-(2-Bromoethyl)tetrahydrofuran (123 mg) was added and the reaction was continued for 2 h. The mixture was quenched with water and extracted with EtOAc (×3). The combined organics were washed with water and brine, dried using a hydrophobic frit and evaporated to give an oil (265 mg). The crude material was purified by normal phase chromatography (ISCO) using 0-15% MeOH/EtOAc as eluent to give the title compound (102 mg).

Workup

  1. waitthe reaction was continued for 2 h
  2. customThe mixture was quenched with water
  3. extractionextracted with EtOAc (×3)
  4. washThe combined organics were washed with water and brine
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-87d1fc8d0ea14d1ea85c41922689c5e2
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

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