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

HRID 2257116Notes

Reaction equation

HRID 2257116 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].[C:12](=O)([O-])[O-].[K+].[K+].IC.[OH-].[Na+]>CN(C)C=O.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

7

Reactant 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 691355-Nitrouracil

Product 1

HCID 27557345-Nitro-1-methyl-uracilYield 77%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

5-nitrouracil (10.00 g, 64 mmole) and potassium carbonate were stirred in dimethylformamide (50 mL) for 15 min. A solid formed. Iodomethane (5.3 mL, 85 mmol) was added and the flask was shaken until the solid dissolved. After the reaction mixture was stirred for 30 min., 2% NaOH (w/v) (200 mL) was added, followed by water (100 mL). The solution was washed with ethyl acetate (100 mL), and the aqueous layer was acidified to pH 3 with 1.0N HCl. A precipitate formed as the pH was lowered. After allowing the heterogeneous solution to stand for 16 hours, the product was filtered, washing with water, and air dried. The title compound was isolated in 77% yield as a yellow powder. m.p. 249°-250° C.

Workup

  1. customA solid formed
  2. dissolutiondissolved
  3. stirringAfter the reaction mixture was stirred for 30 min.
  4. washThe solution was washed with ethyl acetate (100 mL)
  5. customA precipitate formed as the pH
  6. filtrationthe product was filtered
  7. washwashing with water, and air
  8. customdried

Sources & evidence

ORD record
ord-26fb828977dd4cdc86b76f0be61741c6
Source dataset
uspto-grants-1997_08
Patent number
US05656645

Reaction notes

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