Water → 3-(5-Hexenyl)-1-methylthymine

HRID 399758

反応式

HRID 399758 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][CH:18]=[CH2:19].O>CS(C)=O>[CH2:19]([N:7]1[C:8](=[O:9])[C:10]([CH3:11])=[CH:12][N:4]([CH3:3])[C:5]1=[O:6])[CH2:18][CH2:17][CH2:16][CH:15]=[CH2:14]

参加物

6

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 759066-Bromo-1-hexeneHCID 959611,5-Dimethyl-2,4(1H,3H)-pyrimidinedione

生成物 1

HCID 232959493-(5-Hexenyl)-1-methylthymine収率 90%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

3-(5,6-Oxidohexyl)-1-methylthymine was synthesized as follows: A mixture of sodium hydride (343 mg, 14 mmol) and 1-methylthymine (2.00 g, 14 mmol) in dimethylsulfoxide (30 ml) was stirred for 15 minutes, and then 6-bromo-1-hexene (2.30 g, 14 mmol) was added. After stirring for 69 hours, the reaction mixture was poured into water (100 ml) and extracted with dichloromethane (4×50 ml). The combined organic layers were washed with saturated aqueous sodium chloride solution (40 ml), dried over sodium sulfate, and then the solvent was evaporated under vacuum to give a residue which was recrystallized (dichloromethane-ethyl ether) to give 3-(5-hexenyl)-1-methylthymine (2.80 g, 88% yield).

後処理

  1. stirringAfter stirring for 69 hours
  2. extractionextracted with dichloromethane (4×50 ml)
  3. washThe combined organic layers were washed with saturated aqueous sodium chloride solution (40 ml)
  4. dry with materialdried over sodium sulfate
  5. customthe solvent was evaporated under vacuum
  6. customto give a residue which
  7. customwas recrystallized (dichloromethane-ethyl ether)

出典と根拠

ORDレコード
ord-5c875f928bd54eff8cb8cee798da177e
出典データセット
uspto-grants-1998_10
特許番号
US05824677

関連ノート

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