Water → 3-(5-Hexenyl)-1-methylthymine

HRID 1684554Notes

Reaction equation

HRID 1684554 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

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 (2.80g, 88% yield).

Workup

  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)

Sources & evidence

ORD record
ord-fa4fcf7c9a72499584f94b2b43e5658c
Source dataset
uspto-grants-1997_06
Patent number
US05641783

Reaction notes

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