Butanoic acid, 2-(ethoxymethylene)-3-oxo-, ethyl ester → Ethyl-2-methylthio-4-methyl-5-pyrimidine carboxylate

HRID 917393Notes

Reaction equation

HRID 917393 reaction equation
[C:1]([C:4](=[CH:10]OCC)[C:5]([O:7][CH2:8][CH3:9])=[O:6])(=O)[CH3:2].C[NH:15][C:16](=[NH:18])[SH:17].S(=O)(=O)(O)O.[C:24]([O-])(=O)C.[Na+]>CN(C)C=O>[CH3:2][C:1]1[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:10][N:18]=[C:16]([S:17][CH3:24])[N:15]=1

Participants

5

Reactant 3

HCID 97734Butanoic acid, 2-(ethoxymethylene)-3-oxo-, ethyl esterHCID 517045Sodium AcetateHCID 178485225HCID 178485225, compound

Product 1

HCID 188208Ethyl-2-methylthio-4-methyl-5-pyrimidine carboxylateYield 175.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To 100 ml of N,N-dimethylformamide, 18.6 g (100 mmol) of ethyl 2-acetyl-3-ethoxyacrylate, 13.9 g (50 mmol) of sulfuric acid methylisothiourea and 8.2 g (100 mmol) of sodium acetate were suspended, followed by stirring at 80° C. for 4 hours. The reaction liquid was cooled and then poured in ice water. The crystal precipitated was filtered, washed with water and dried to obtain 18.6 g (yield: 88%) of ethyl 4-methyl-2-(methylthio)pyrimidine-5-carboxylate.

Workup

  1. customThe reaction liquid
  2. temperaturewas cooled
  3. customThe crystal precipitated
  4. filtrationwas filtered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-5a9ad7cda0e547e5b20173e70c707922
Source dataset
uspto-grants-2007_09
Patent number
US07273878B2

Reaction notes

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