Potassium Carbonate → Ethyl 4-methyl-2-(methylthio)-6-oxo-1,6-dihydropyrimidine-5-carboxylate

HRID 390037Notes

Reaction equation

HRID 390037 reaction equation
[CH3:1][CH:2]1[CH:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:6](=[O:13])[NH:5][C:4]([S:14][CH3:15])=[N:3]1.BrN1C(=O)CCC1=O.C(=O)([O-])[O-].[K+].[K+]>C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C(Cl)(Cl)(Cl)Cl>[CH3:1][C:2]1[N:3]=[C:4]([S:14][CH3:15])[NH:5][C:6](=[O:13])[C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 67184N-bromobutanimideHCID 22225415Ethyl 4-methyl-2-(methylthio)-6-oxo-1,4,5,6-tetrahydro-5-pyrimidinecarboxylate

Product 1

HCID 135504073Ethyl 4-methyl-2-(methylthio)-6-oxo-1,6-dihydropyrimidine-5-carboxylateYield 78%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A round bottom flask was charged with ethyl 4-methyl-2-(methylthio)-6-oxo-1,4,5,6-tetrahydro-5-pyrimidinecarboxylate (11.2 g, 48.7 mmol), N-bromo succinimide (8.67 g, 48.7 mmol), benzoyl peroxide (0.65 g, 2.7 mmol), potassium carbonate (67 g, 487 mmol) and carbon tetrachloride (700 mL). The reaction was heated to reflux for 45 min and cooled to room temperature. The reaction was quenched with to water (500 mL) and washed with methylene chloride. Aqueous phase was acidified by dropwise addition of conc. HCl and extracted with methylene chloride. The extract was dried over MgSO4, filtered, and evaporated under vacuum to afford the product (8.2 g, 78% yield).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 45 min
  3. customThe reaction was quenched with to water (500 mL)
  4. washwashed with methylene chloride
  5. additionAqueous phase was acidified by dropwise addition of conc. HCl
  6. extractionextracted with methylene chloride
  7. dry with materialThe extract was dried over MgSO4
  8. filtrationfiltered
  9. customevaporated under vacuum

Sources & evidence

ORD record
ord-6523e80c33754414a84f05b7f593da4d
Source dataset
uspto-grants-2013_02
Patent number
US08383635B2

Reaction notes

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