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

HRID 1738793
ノート
印刷プレビュー

反応式

HRID 1738793 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028
Tetrahydrofuran
溶媒
2 回
HCID 8058Hexane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ab80205827d045e28210f06af697e415
出典データセット
uspto-grants-1999_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05965555

反応ノート

読み込み中…

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