Acetic Acid → 3-Pyridylmethyl-2-methylthio-4-pyrimidone

HRID 1855843Notes

Reaction equation

HRID 1855843 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C:8]2[C:9](=[O:15])[NH:10][C:11](=[S:14])[NH:12][CH:13]=2)[CH:2]=1.CI.[OH-].[Na+].[C:20](O)(=O)C>O.C(O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C:8]2[C:9](=[O:15])[NH:10][C:11]([S:14][CH3:20])=[N:12][CH:13]=2)[CH:2]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 14338580HCID 14338580, compound

Product 1

HCID 127838233-Pyridylmethyl-2-methylthio-4-pyrimidone

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 5-(3-pyridylmethyl)-2-thiouracil (11.0 g), methyl iodide (7.1 g) and sodium hydroxide (4.2 g) in water (150 ml) and ethanol (150 ml) was stirred at 65° for 40 minutes, allowed to cool and acetic acid was added to pH5. The solution was partially evaporated, cooled and filtered to give 5-(3-pyridylmethyl)-2-methylthio-4-pyrimidone, m.p. 247°-9° (ex. ethanol-acetic acid).

Workup

  1. temperatureto cool
  2. customThe solution was partially evaporated
  3. temperaturecooled
  4. filtrationfiltered

Sources & evidence

ORD record
ord-03c13c613d994a0c9f00845b5bd3c2bd
Source dataset
uspto-grants-1980_08
Patent number
US04216318

Reaction notes

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