Methanol → 7-Benzyl-1-(2-propoxyethyl)-3-propylxanthine

HRID 323866

반응식

HRID 323866 반응식
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([N:14]1[C:22]2[C:21](=[O:23])[NH:20][C:19](=[O:24])[N:18]([CH2:25][CH2:26][CH3:27])[C:17]=2[N:16]=[CH:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH2:28]([O:31][CH2:32][CH2:33]Cl)[CH2:29][CH3:30].CO>CN(C)C=O.O>[CH2:7]([N:14]1[C:22]2[C:21](=[O:23])[N:20]([CH2:33][CH2:32][O:31][CH2:28][CH2:29][CH3:30])[C:19](=[O:24])[N:18]([CH2:25][CH2:26][CH3:27])[C:17]=2[N:16]=[CH:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

참가 물질

7

반응물 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 1235061-(2-Chloroethoxy)propaneHCID 220073027-Benzyl-3-propylxanthine

생성물 1

HCID 220073057-Benzyl-1-(2-propoxyethyl)-3-propylxanthine

시약·촉매·용매 2

HCID 962Water용매2회HCID 6228Dimethylformamide용매

실험 절차

1.7 g (12.48 mmol) of potassium carbonate were added at 60° C. to a suspension of 2.2 g (7.8 mmol) of 7-benzyl-3-propylxanthine (prepared according to Example 4a) in 70 ml of dimethylformamide and the mixture was stirred at this temperature for one hour. 1.3 ml (10.14 mmol) of 2-propoxyethyl chloride were then added dropwise and the mixture was stirred at 80° C. for 10 hours. 1.2 ml of methanol and 14 ml of water were then added, and the mixture was allowed to stand overnight, treated with a further 70 ml of water and extracted three times using 84 ml of methyl tert-butyl ether each time. The combined organic phases were washed twice with 42 ml of water each time, dried using magnesium sulfate and concentrated under reduced pressure. The crude product was purified by flash chromatography on a silica gel column, dichloromethae/methanol (19/0.1).

후처리

  1. stirringthe mixture was stirred at 80° C. for 10 hours
  2. waitto stand overnight
  3. extractionextracted three times
  4. washThe combined organic phases were washed twice with 42 ml of water each time
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by flash chromatography on a silica gel column, dichloromethae/methanol (19/0.1)

출처 및 근거

ORD 기록
ord-2460697181e740868704adf624e8fff0
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06214992B1

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