Water → 3-(5-Hexenyl)-1-methyluracil

HRID 1955976Notes

Reaction equation

HRID 1955976 reaction equation
[H-].[Na+].[CH3:3][N:4]1[CH:11]=[CH:10][C:8](=[O:9])[NH:7][C:5]1=[O:6].Br[CH2:13][CH2:14][CH2:15][CH2:16][CH:17]=[CH2:18].O>CS(C)=O>[CH2:18]([N:7]1[C:8](=[O:9])[CH:10]=[CH:11][N:4]([CH3:3])[C:5]1=[O:6])[CH2:17][CH2:16][CH2:15][CH:14]=[CH2:13]

Participants

6

Reactant 4

HCID 962WaterHCID 120091-MethyluracilHCID 24758Sodium hydrideHCID 759066-Bromo-1-hexene

Product 1

HCID 232958743-(5-Hexenyl)-1-methyluracilYield 72%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

3-(5,6-Oxidohexyl)-1-methyluracil was synthesized as follows: A mixture of sodium hydride (86 mg, 3.6 mmol) and 1-methyluracil (500 mg, 4 mmol) in dimethyl sulfoxide (25 ml) was stirred for 15 minutes, and then 6-bromo-1-hexene (647 mg, 4 mmol) was added. After stirring for 20 hours, the reaction mixture was poured into water (50 ml) and extracted with 20% ethanol-dichloromethane (3×50 ml). The combined organic layers were washed with saturated aqueous sodium chloride solution (20 ml) and dried over sodium sulfate. The solvent was evaporated under vacuum to give a residue which was purified by column chromatography (silica, ethyl acetate) to give 3-(5-hexenyl)-1-methyluracil (598 mg, 72% yield).

Workup

  1. stirringAfter stirring for 20 hours
  2. extractionextracted with 20% ethanol-dichloromethane (3×50 ml)
  3. washThe combined organic layers were washed with saturated aqueous sodium chloride solution (20 ml)
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was evaporated under vacuum
  6. customto give a residue which
  7. customwas purified by column chromatography (silica, ethyl acetate)

Sources & evidence

ORD record
ord-05c32bdc160d462986522f5de5c44164
Source dataset
uspto-grants-1998_07
Patent number
US05777117

Reaction notes

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