Potassium Carbonate → 7-Benzyl-1-(4-chlorophenoxymethyl)-3-methylxanthine

HRID 323874

반응식

HRID 323874 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]([CH3:25])[C:17]=2[N:16]=[CH:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[Cl:26][C:27]1[CH:35]=[CH:34][C:30]([O:31][CH2:32]Cl)=[CH:29][CH:28]=1>CN(C)C=O>[CH2:7]([N:14]1[C:22]2[C:21](=[O:23])[N:20]([CH2:32][O:31][C:30]3[CH:34]=[CH:35][C:27]([Cl:26])=[CH:28][CH:29]=3)[C:19](=[O:24])[N:18]([CH3:25])[C:17]=2[N:16]=[CH:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 88801alpha,4-DichloroanisoleHCID 6856307-Benzyl-3-methylxanthine

생성물 1

HCID 220073197-Benzyl-1-(4-chlorophenoxymethyl)-3-methylxanthine

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

2.59 g (19.0 mmol) of potassium carbonate were added at 60° C. to a suspension of 3.0 g (12.0 mmol) of 7-benzyl-3-methylxanthine (prepared according to Example 1a) in 50 ml of dimethylformamide and the mixture was stirred at this temperature for one hour. 2.69 g (15.0 mmol) of 4-chlorophenoxymethyl chloride were then added dropwise and the mixture was stirred at 80° C. for 8 hours. The crude mixture was then filtered, the filtrate was concentrated under reduced pressure, the residue was taken up in dichloromethane, and the solution was washed once with 1 N sodium hydroxide solution and twice with water. The organic phases were dried using magnesium sulfate and concentrated under reduced pressure. The crude product was purified by flash chromatography on a silica gel column, dichloromethane/methanol (19.8/0.2) Yield: 4.15 g (87% of theory); melting point: 96° C.

후처리

  1. stirringthe mixture was stirred at 80° C. for 8 hours
  2. filtrationThe crude mixture was then filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. washthe solution was washed once with 1 N sodium hydroxide solution and twice with water
  5. customThe organic phases were dried
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by flash chromatography on a silica gel column, dichloromethane/methanol (19.8/0.2) Yield: 4.15 g (87% of theory)

출처 및 근거

ORD 기록
ord-1e17ee0626d943439926e7915051c237
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06214992B1

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