Water → HCID 57215608, compound

HRID 1954130Notes

Reaction equation

HRID 1954130 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>[CH:13]([N:7]1[C:8](=[O:9])[CH:10]=[CH:11][N:4]([CH3:3])[C:5]1=[O:6])=[CH:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

6

Reactant 4

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

Product 1

HCID 57215608HCID 57215608, compoundYield 71,786.297%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

This example illustrates a synthesis of 3-(5,6-Oxidohexyl)-1-methyluracil (inventive compound no. 1808). Sodium hydride (86 mg, 3.6 mmol) was added to a stirring solution of 1-methyluracil (500 mg, 4 mmol) in dimethyl sulfoxide (25 mL). After 15 minutes, 6-bromo-1-hexene (647 mg, 4 mmol) was added and the mixture stirred further for 20 hours. The reaction mixture was then poured into water (50 mL) and extracted with 20% ethanol/dichloromethane (3×50 mL). The combined organic layers were washed with aqueous saturated salt solution (20 mL) and dried over sodium sulfate. The solvent was evaporated under vacuum to give a residue which was purified by chromatography with silica and ethyl acetate to yield 598 g (72% yield) of 3-hexenyl-1-methyluracil (inventive compound no. 1800).

Workup

  1. extractionextracted with 20% ethanol/dichloromethane (3×50 mL)
  2. washThe combined organic layers were washed with aqueous saturated salt solution (20 mL)
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was evaporated under vacuum
  5. customto give a residue which
  6. customwas purified by chromatography with silica and ethyl acetate

Sources & evidence

ORD record
ord-230aada84b624c6594f49f2f0f6463a7
Source dataset
uspto-grants-2000_09
Patent number
US06121270

Reaction notes

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