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

HRID 1378995

반응식

HRID 1378995 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
50 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-40e6c0c6eb144d9aae726f345076b4ae
출처 데이터셋
uspto-grants-1997_09
특허 번호
US05670498

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