Dimethyl Sulfoxide → HCID 69732887, compound

HRID 2416417Notes

Reaction equation

HRID 2416417 reaction equation
[NH2:1][C:2]1[N:7](C)[C:6](=[O:9])[NH:5][C:4](=[O:10])[CH:3]=1.Cl[CH2:12][CH2:13][CH2:14][CH2:15][C@H:16]([O:18][CH3:19])[CH3:17].CS(C)=O.[H-].[Na+]>O>[NH2:1][C:2]1[NH:7][C:6](=[O:9])[N:5]([CH2:12][CH2:13][CH2:14][CH2:15][C@H:16]([O:18][CH3:19])[CH3:17])[C:4](=[O:10])[CH:3]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 755206-Amino-1-methyluracilHCID 86590997HCID 86590997, compound

Product 1

HCID 69732887HCID 69732887, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 6-amino-1-methyluracil (141 mg, 1.0 mmol), (R)-1-chloro-5-methoxyhexane (150 mg, 1.0 mmol), dimethylsulfoxide (2 ml) and sodium hydride (30 mg, 1.2 mmol) was heated to 90° C. for 18 hours. After cooling to room temperature, the mixture was treated with water (7 ml) and extracted with ethyl acetate. The extract was dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel eluting with ethyl acetate followed by 5% methanol-ethyl acetate to provide (R)-6-amino-3-(5-methoxyhexyl)uracil (152 mg, 60% yield) as an oil.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extract was dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-fdcea853794a462daa0737badd04fc57
Source dataset
uspto-grants-2004_11
Patent number
US06825180B2

Reaction notes

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