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

HRID 869367ノート

反応式

HRID 869367 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
70 °C

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-030d4a86f7f34a509a7a4c1538124656
出典データセット
uspto-grants-2015_03
特許番号
US08969362B2

反応ノート

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