Methyl iodide → 5-Nitro-1-methyl-uracil

HRID 397012Notes

Reaction equation

HRID 397012 reaction equation
[N+:1]([C:4]1[C:5](=[O:11])[NH:6][C:7](=[O:10])[NH:8][CH:9]=1)([O-:3])=[O:2].[CH3:12][Si](O[Si](C)(C)C)(C)C.IC>CN(C)C=O>[N+:1]([C:4]1[C:5](=[O:11])[NH:6][C:7](=[O:10])[N:8]([CH3:12])[CH:9]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 867511475-Nitrouracil bis(trimethylsilyl)ether

Product 1

HCID 27557345-Nitro-1-methyl-uracil

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-nitrouracil (10.00g, 64 mmole), 1,1,1-3,3,3-hexamethyldisilazane (40 mL, 190 mmole) and chlorotrimethylsilane(4.0 mL, 0.32 mmole) are heated to reflux for 24 hours. The solution is concentrated under reduced pressure to afford 5-nitrouracil bis (trimethylsilyl) ether. 5-nitrouracil bis(trimethylsilyl)ether (10.0 g, 24 mmole), dimethylformamide (50 mL) and iodomethane (3.0 mL, 49 mmole) are heated in an 80° C. oil bath for 24 hours. Ice water is added, and the mixture is stirred for 30 minutes, then extracted with dichloromethane (3×). The combined organic layers are dried over magnesium sulfate, filtered, and concentrated under reduced pressure to give the title compound.

Workup

  1. extractionextracted with dichloromethane (3×)
  2. dry with materialThe combined organic layers are dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2b5ea075f56a4097ad598393fdc242c1
Source dataset
uspto-grants-2003_08
Patent number
US06608204B1

Reaction notes

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