Water → 3-(5-Hexenyl)-1-methylthymine

HRID 356619

반응식

HRID 356619 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

HCID 232959493-(5-Hexenyl)-1-methylthymine수율 90%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-76810501d01e40cba8da366b850b3c3c
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05837703

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