Methyl iodide → Istradefylline

HRID 1081763ノート

反応式

HRID 1081763 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:23]=[CH:24][C:25]=1[O:26][CH3:27])/[CH:6]=[CH:7]/[C:8]1[NH:16][C:15]2[C:14](=[O:17])[N:13]([CH2:18][CH3:19])[C:12](=[O:20])[N:11]([CH2:21][CH3:22])[C:10]=2[N:9]=1.[C:28](=O)([O-])[O-].[K+].[K+].CI>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:23]=[CH:24][C:25]=1[O:26][CH3:27])/[CH:6]=[CH:7]/[C:8]1[N:16]([CH3:28])[C:15]2[C:14](=[O:17])[N:13]([CH2:18][CH3:19])[C:12](=[O:20])[N:11]([CH2:21][CH3:22])[C:10]=2[N:9]=1

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 64457888-[(1E)-2-(3,4-Dimethoxyphenyl)ethenyl]-1,3-diethyl-3,9-dihydro-1H-purine-2,6-dione

生成物 1

HCID 5311037Istradefylline収率 68%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Compound 64 (1.20 g, 3.24 mmol) obtained in Example 7 was dissolved in 25 ml of dimethylformamide. To the solution were added 1.12 g (8.10 mmol) of potassium carbonate and subsequently 0.40 ml (6.49 mmol) of methyl iodide, and the resultant mixture was stirred at 50° C. for 30 minutes. After cooling, insoluble matters were filtered off, and 100 ml of water was added to the filtrate. The mixture was extracted three times with 50 ml of chloroform. The extract was washed twice with water and once with a saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate, followed by evaporation under reduced pressure. The obtained crude crystals were purified by silica gel column chromatography (eluent: 40% ethyl acetate/hexane), followed by recrystallization from isopropanol to give 840 mg (yield 68%) of Compound 65 as pale yellow needles.

後処理

  1. temperatureAfter cooling
  2. filtrationinsoluble matters were filtered off
  3. addition100 ml of water was added to the filtrate
  4. extractionThe mixture was extracted three times with 50 ml of chloroform
  5. washThe extract was washed twice with water and once with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. customfollowed by evaporation under reduced pressure
  8. customThe obtained crude crystals
  9. customwere purified by silica gel column chromatography (eluent: 40% ethyl acetate/hexane)
  10. customfollowed by recrystallization from isopropanol

出典と根拠

ORDレコード
ord-347e548158944ed69b213e62089c0131
出典データセット
uspto-grants-1996_12
特許番号
US05587378

反応ノート

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