Acetic Acid → 2-methylthio-5-(2-methylpyrid-5-ylmethyl)-1H-pyrimid-4-one

HRID 2413161Notes

Reaction equation

HRID 2413161 reaction equation
CI.[CH3:3][C:4]1[N:9]=[CH:8][C:7]([CH2:10][C:11]2[C:12](=[O:18])[NH:13][C:14](=[S:17])[NH:15][CH:16]=2)=[CH:6][CH:5]=1.[OH-].[Na+].[C:21](O)(=O)C>O.C(O)C>[CH3:3][C:4]1[N:9]=[CH:8][C:7]([CH2:10][C:11]2[C:12](=[O:18])[NH:13][C:14]([S:17][CH3:21])=[N:15][CH:16]=2)=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 12783848HCID 12783848, compound

Product 1

HCID 127838272-methylthio-5-(2-methylpyrid-5-ylmethyl)-1H-pyrimid-4-one

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Methyl iodide (13.79 g) was added to a stirred solution of 5-(6-methyl-3-pyridylmethyl)-2-thiouracil (22.66 g) and sodium hydroxide (8.0 g) in water (250 ml) and ethanol (250 ml), and the mixture was heated at 70° for 1 hour and stirred at room temperature overnight. Acetic acid was added to pH 5 and the volume of the mixture was evaporated to a volume of 50 ml. The solid was filtered off and was recrystallised from ethanol-acetic acid to give 5-(6-methyl-3-pyridylmethyl)-2-methylthio-4-pyrimidone (10.16 g) m.p. 197°-197.5°.

Workup

  1. temperaturethe mixture was heated at 70° for 1 hour
  2. customthe volume of the mixture was evaporated to a volume of 50 ml
  3. filtrationThe solid was filtered off
  4. customwas recrystallised from ethanol-acetic acid

Sources & evidence

ORD record
ord-29b069de5ea8463985b7940ddf211e98
Source dataset
uspto-grants-1985_01
Patent number
US04496567

Reaction notes

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