Ethanol → 5-benzyl-6-methyl-2-methylsulfanyl-1H-pyrimidin-4-one

HRID 2419002Notes

Reaction equation

HRID 2419002 reaction equation
[CH2:1]([C:8]1[C:9](=[O:16])[NH:10][C:11](=[S:15])[NH:12][C:13]=1[CH3:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[CH2:19](O)C.CI>O>[CH2:1]([C:8]1[C:9](=[O:16])[NH:10][C:11]([S:15][CH3:19])=[N:12][C:13]=1[CH3:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 6973265-Benzyl-6-methylthiouracil

Product 1

HCID 1354225835-benzyl-6-methyl-2-methylsulfanyl-1H-pyrimidin-4-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

5-Benzyl-6-methylthiouracil (6.0 gms) and sodium hydroxide (1.06 gms) were dissolved in water (30 mls). The solution was cooled and ethanol (60 mls) and methyl iodide (3.67 gms) added with stirring. The mixture was heated at 60° C for 178 hour, cooled and the resulting solid collected and water-washed. A second crop of solid was obtained by acidification of the filtrate to pH=4 with acetic acid. Recrystallisation from ethanol produced 5-benzyl-6-methyl-2-methylthio-4-pyrimidone (5.53 gms) m.p. = 220°-221.5° C.

Workup

  1. temperatureThe solution was cooled
  2. temperaturecooled
  3. customthe resulting solid collected
  4. washwater-washed
  5. customA second crop of solid was obtained by acidification of the filtrate to pH=4 with acetic acid
  6. customRecrystallisation from ethanol

Sources & evidence

ORD record
ord-bfcd48df539e4941be1a51e6bed0d443
Source dataset
uspto-grants-1978_08
Patent number
US04104381

Reaction notes

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