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

HRID 1251348Notes

Reaction equation

HRID 1251348 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 (10.00 g, 64 mmole), 1,1,1-3,3,3-hexamethyldisilazane (40 mL, 190 mmole) and chlorotrimethylsilane (4.0 mL, 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. An alternative method of preparing the title compound is described in Example 108.

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-71c1b0be71284a2895506f4cd35d2478
Source dataset
uspto-grants-2002_01
Patent number
US06342504B1

Reaction notes

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