Potassium Carbonate → 2-Butoxy-9-[2-(3-methoxycarbonylphenoxy)ethyl]adenine

HRID 869367Notes

Reaction equation

HRID 869367 reaction equation
[CH2:1]([O:5][C:6]1[N:14]=[C:13]2[C:9]([NH:10][CH:11]=[N:12]2)=[C:8]([NH2:15])[N:7]=1)[CH2:2][CH2:3][CH3:4].C(=O)([O-])[O-].[K+].[K+].Br[CH2:23][CH2:24][O:25][C:26]1[CH:27]=[C:28]([CH:33]=[CH:34][CH:35]=1)[C:29]([O:31][CH3:32])=[O:30]>CN(C=O)C>[CH2:1]([O:5][C:6]1[N:14]=[C:13]2[C:9]([N:10]=[CH:11][N:12]2[CH2:23][CH2:24][O:25][C:26]2[CH:35]=[CH:34][CH:33]=[C:28]([C:29]([O:31][CH3:32])=[O:30])[CH:27]=2)=[C:8]([NH2:15])[N:7]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 10491483Methyl 3-(2-bromoethoxy)benzoateHCID 229289002-butoxy-9H-purin-6-amine

Product 1

HCID 231585082-Butoxy-9-[2-(3-methoxycarbonylphenoxy)ethyl]adenineYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
70 °C

Procedure

To 2-butoxyadenine (727 mg, 3.5 mmol) and potassium carbonate (727 mg, 5.3 mmol) was added DMF (35 ml), and the mixture was stirred at 70° C. for 2 hours. Then a solution of methyl 3-(2-bromoethoxy)benzoate obtained in Reference Example 1 (1.0 g, 3.9 mmol) in DMF (2 ml) was added thereto under ice-cooling, followed by stirring at room temperature for 3 hours. The solvent was removed under reduced pressure, and to the residue was added water. The mixture was neutralized with concentrated hydrochloric acid and extracted with chloroform (methanol 5%). The organic layer was washed with water and saturated brine, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give, as white crystal, 1.1 g (2.9 mmol) of the titled compound. Yield: 81%.

Workup

  1. additionwas added
  2. temperatureunder ice-cooling
  3. stirringby stirring at room temperature for 3 hours
  4. customThe solvent was removed under reduced pressure
  5. additionto the residue was added water
  6. extractionextracted with chloroform (methanol 5%)
  7. washThe organic layer was washed with water and saturated brine
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-030d4a86f7f34a509a7a4c1538124656
Source dataset
uspto-grants-2015_03
Patent number
US08969362B2

Reaction notes

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