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Hydrochloric Acid → 1-(6-Dibutylamino-3-hydroxy-3-methyl-4-hexynyl)-3-methyl-7-propyl-xanthine

HRID 1738793
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인쇄 미리보기

반응식

HRID 1738793 반응식
[CH2:1]([Li])CCC.[CH2:6]([N:10]([CH2:15][C:16]#C)[CH2:11][CH2:12][CH2:13][CH3:14])[CH2:7][CH2:8][CH3:9].[CH3:18][N:19]1[C:27]2[N:26]=[CH:25][N:24]([CH2:28][CH2:29][CH3:30])[C:23]=2[C:22](=[O:31])[N:21]([CH2:32][CH2:33][C:34](=[O:36])[CH3:35])[C:20]1=[O:37].Cl>CCCCCC.O1CCCC1>[CH2:11]([N:10]([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:15][C:16]#[C:35][C:34]([OH:36])([CH3:1])[CH2:33][CH2:32][N:21]1[C:22](=[O:31])[C:23]2[N:24]([CH2:28][CH2:29][CH3:30])[CH:25]=[N:26][C:27]=2[N:19]([CH3:18])[C:20]1=[O:37])[CH2:12][CH2:13][CH3:14]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 1387323-Dibutylamino-1-propyneHCID 153909233-Methyl-1-(3-oxobutyl)-7-propylxanthineHCID 178418339Butyllithium

생성물 1

HCID 153909091-(6-Dibutylamino-3-hydroxy-3-methyl-4-hexynyl)-3-methyl-7-propyl-xanthine

시약·촉매·용매 2

HCID 8028
Tetrahydrofuran
용매
2회
HCID 8058Hexane용매

실험 절차

6.73 ml (10.77 mmol) of a 15% strength butyllithium solution in n-hexane were slowly added dropwise to a solution of 2.09 ml (10.77 mmol) of N,N-dibutyl-2-propynylamine in 20 ml of tetrahydrofuran at -65° C. The mixture was stirred at -60° C. to -65° C. for one hour and warmed to room temperature, and a solution of 2.0 g (7.18 mmol) of 3-methyl-1-(3-oxobutyl)-7-propylxanthine in 30 ml of tetrahydrofuran was added. The slightly exothermic reaction was complete after 30 minutes. The mixture was adjusted to pH 5-6 with 1 N hydrochloric acid and partitioned between dichloromethane and water. The organic phase was washed with water, dried with magnesium sulfate and concentrated under reduced pressure. The oily crude product was purified by flash chromatography, dichloromethane/methanol =19/0.75.

후처리

  1. customThe slightly exothermic reaction
  2. waitwas complete after 30 minutes
  3. custompartitioned between dichloromethane and water
  4. washThe organic phase was washed with water
  5. dry with materialdried with magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe oily crude product was purified by flash chromatography, dichloromethane/methanol =19/0.75

출처 및 근거

ORD 기록
ord-ab80205827d045e28210f06af697e415
출처 데이터셋
uspto-grants-1999_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05965555

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