Water → 2-(Methylthio)-1H-pyrimidin-4-one

HRID 598080

Reaction equation

HRID 598080 reaction equation
[NH:1]1[CH:8]=[CH:7][C:5](=[O:6])[NH:4][C:2]1=[S:3].[OH-].[Na+].O.[CH3:12]I>C(O)C>[CH3:12][S:3][C:2]1[NH:4][C:5](=[O:6])[CH:7]=[CH:8][N:1]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 1269845Thiouracil

Product 1

HCID 798232-(Methylthio)-1H-pyrimidin-4-oneYield 47%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
30 °C

Procedure

A mixture of 12.8 g (99.9 mmol) of 2-thiouracil and 4.3 g (108 mmol) of sodium hydroxide was placed in 500 ml Erlenmeyer flask, and dissolved on the oil bath with a minimum amount of water. Twice the volume of 99% ethanol was then added, the solution cooled to 30° C., and 6.3 ml (99.9 mmol) of methyl iodide added. The solution was heated to 60° C. for 20 min, then cooled to room temp. The precipitate was filtered off, and, after acidifying the filtrate with acetic acid, the excess solvent was removed in vacuo. The combined precipitates were thoroughly washed with water and recrystallized from ethanol to give 6.0 g (47%) of product.

Workup

  1. temperatureThe solution was heated to 60° C. for 20 min
  2. temperaturecooled to room temp
  3. filtrationThe precipitate was filtered off
  4. customthe excess solvent was removed in vacuo
  5. customThe combined precipitates
  6. washwere thoroughly washed with water
  7. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-79212637617b4b7db93dbe08c1ec635e
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Linked notes

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