2-Methyl-2-thiopseudourea → HCID 178418413, compound

HRID 1396828Notes

Reaction equation

HRID 1396828 reaction equation
[CH3:1][S:2][C:3](=[NH:5])[NH2:4].C([O:8][CH:9]=[C:10]([C:16]#[N:17])[C:11](OCC)=O)C.C([O-])([O-])=O.[K+].[K+]>CCO>[OH:8][C:9]1[C:10]([C:16]#[N:17])=[CH:11][N:4]=[C:3]([S:2][CH3:1])[N:5]=1

Participants

5

Reactant 3

HCID 51422-Methyl-2-thiopseudoureaHCID 11430Potassium CarbonateHCID 789432-Propenoic acid, 2-cyano-3-ethoxy-, ethyl ester

Product 1

HCID 178418413HCID 178418413, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Methyl-2-thiopseudourea (5 mmol) and ethyl ethoxymethylenecyanoacetate (5 mmol) were dissolved in 20 ml EtOH. To this was added K2CO3 (10 mmol). After the mixture was refluxed for 48 h, it was cooled to room temperature and filtered. The solvent was concentrated in vacuo and purified by column chromatography to give 4-hydroxy-2-(methylthio)pyrimidine-5-carbonitrile in a yield of 65%.

Workup

  1. temperatureAfter the mixture was refluxed for 48 h
  2. filtrationfiltered
  3. concentrationThe solvent was concentrated in vacuo
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-62df6d7166b84ef59c7f91b914e11849
Source dataset
uspto-grants-2014_12
Patent number
US08901143B2

Reaction notes

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