Methyl iodide → (E)-8-(3-Bromostyryl)-1,3-diethyl-7-methylxanthine (6d)

HRID 1378995

反応式

HRID 1378995 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=1)/[CH:5]=[CH:6]/[C:7]1[NH:15][C:14]2[C:13](=[O:16])[N:12]([CH2:17][CH3:18])[C:11](=[O:19])[N:10]([CH2:20][CH3:21])[C:9]=2[N:8]=1.[C:25](=O)([O-])[O-].[K+].[K+].CI>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=1)/[CH:5]=[CH:6]/[C:7]1[N:15]([CH3:25])[C:14]2[C:13](=[O:16])[N:12]([CH2:17][CH3:18])[C:11](=[O:19])[N:10]([CH2:20][CH3:21])[C:9]=2[N:8]=1

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 64489301H-Purine-2,6-dione, 3,7-dihydro-8-(2-(3-bromophenyl)ethenyl)-1,3-diethyl-, (E)-

生成物 1

HCID 6448931(E)-8-(3-Bromostyryl)-1,3-diethyl-7-methylxanthine (6d)

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

Compound g (2.5 g, 6.43 mmol) obtained in Reference Example 7 was dissolved in 20 ml of dimethylformamide. To the solution were added 2.22 g (16.1 mmol) of potassium carbonate and subsequently 0.8 ml (12.9 mmol) of methyl iodide, and the resulting mixture was stirred at 50° C. for 70 minutes. After cooling, insoluble matters were filtered off and water was added to the filtrate. The mixture was extracted three times with chloroform. The extract was washed three times with water and subsequently twice with a saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate. Evaporation under reduced pressure gave 2.37 g (yield 92%) of crude Compound h as a yellow solid, which was further recrystallized from cyctohexane/toluene to give Compound h as a yellow powder.

後処理

  1. temperatureAfter cooling
  2. filtrationinsoluble matters were filtered off
  3. additionwater was added to the filtrate
  4. extractionThe mixture was extracted three times with chloroform
  5. washThe extract was washed three times with water
  6. dry with materialsubsequently twice with a saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate
  7. customEvaporation under reduced pressure
  8. customgave 2.37 g (yield 92%) of crude Compound h as a yellow solid, which
  9. customwas further recrystallized from cyctohexane/toluene

出典と根拠

ORDレコード
ord-40e6c0c6eb144d9aae726f345076b4ae
出典データセット
uspto-grants-1997_09
特許番号
US05670498

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