Water → 3-(10-Undecenyl)-1-methylthymine

HRID 361525

反応式

HRID 361525 の反応式
[H-].[Na+].[CH3:3][N:4]1[CH:12]=[C:10]([CH3:11])[C:8](=[O:9])[NH:7][C:5]1=[O:6].Br[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH:23]=[CH2:24].O>CS(C)=O>[CH2:24]([N:7]1[C:8](=[O:9])[C:10]([CH3:11])=[CH:12][N:4]([CH3:3])[C:5]1=[O:6])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH:15]=[CH2:14]

参加物

6

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 959611,5-Dimethyl-2,4(1H,3H)-pyrimidinedioneHCID 28414811-Bromo-1-undecene

生成物 1

HCID 232959793-(10-Undecenyl)-1-methylthymine収率 83.7%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

This example illustrates a synthesis of 3-(11,10-Oxidoundecyl)-1-methylthymine (inventive compound no. 1932). Sodium hydride (95%) (168 mg, 7 mmol) was added to a solution of 1-methylthymine (700.5 mg, 5 mmol) in dimethylsulfoxide (15 mL). After 20 minutes of stirring, 1-bromundec-10-ene (1.165 g, 5 mmol) was added and stirred for 12 hours at room temperature. The reaction mixture was then poured into a separatory funnel containing 100 mL of water and extracted with dichloromethane (5×75 mL). The organic extracts were combined, washed with water (50 mL) and saturated aqueous salt solution (50 mL), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The crude product obtained was further purified by flash chromatography over silica gel using a 20% ethyl acetate/hexane eluant to yield 1.22 g (83.7% yield) 3-(10-undecenyl)-1-methylthymine (inventive compound no. 1931).

後処理

  1. stirringstirred for 12 hours at room temperature
  2. additionThe reaction mixture was then poured into a separatory funnel
  3. extractionextracted with dichloromethane (5×75 mL)
  4. washwashed with water (50 mL) and saturated aqueous salt solution (50 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product obtained
  8. customwas further purified by flash chromatography over silica gel using a 20% ethyl acetate/hexane eluant

出典と根拠

ORDレコード
ord-9650c1683f5b4c38b22fd896d001828b
出典データセット
uspto-grants-1999_02
特許番号
US05866576

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