Methyl iodide → 2-(Methylsulfanyl)-5-[(pyridin-4-yl)methyl]pyrimidin-4(3H)-one

HRID 1855835Notes

Reaction equation

HRID 1855835 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][C:8]2[C:9](=[O:15])[NH:10][C:11](=[S:14])[NH:12][CH:13]=2)=[CH:3][CH:2]=1.[CH3:16]I.[OH-].[Na+]>O.C(O)C>[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][C:8]2[C:9](=[O:15])[NH:10][C:11]([S:14][CH3:16])=[N:12][CH:13]=2)=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 143385795-(4-Pyridylmethyl)-2-thiouracil

Product 1

HCID 143385852-(Methylsulfanyl)-5-[(pyridin-4-yl)methyl]pyrimidin-4(3H)-one

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 5-(4-pyridylmethyl)-2-thiouracil (11.0 g), methyl iodide (7.2 g) and sodium hydroxide (2.1 g) in water (50 ml) and ethanol (100 ml) was stirred at 60° for 30 minutes, allowed to cool and filtered to give 5-(4-pyridylmethyl)-2-methylthio-4-pyrimidone m.p. 179°-182° (ethanol).

Workup

  1. temperatureto cool
  2. filtrationfiltered

Sources & evidence

ORD record
ord-63092aa426514473b17b330ba51d79f6
Source dataset
uspto-grants-1980_08
Patent number
US04216318

Reaction notes

Loading…