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

HRID 485643Notes

Reaction equation

HRID 485643 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 1/2 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-742c98ff561348c380b4bd890f855b6e
Source dataset
uspto-grants-1985_08
Patent number
US04537779

Reaction notes

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