Ethyl Acetoacetate → 6-Methyl-2-(methylsulfanyl)pyrimidin-4(1H)-one

HRID 1893878Notes

Reaction equation

HRID 1893878 reaction equation
S(O)(O)(=O)=O.[CH3:6][S:7][C:8](=[NH:10])[NH2:9].C(=O)([O-])[O-].[Na+].[Na+].[C:17](OCC)(=[O:22])[CH2:18][C:19]([CH3:21])=O>O>[CH3:21][C:19]1[N:9]=[C:8]([S:7][CH3:6])[NH:10][C:17](=[O:22])[CH:18]=1

Participants

5

Reactant 3

HCID 8868Ethyl AcetoacetateHCID 10340Sodium CarbonateHCID 752702-Methyl-2-thiopseudourea sulfate

Product 1

HCID 1354005076-Methyl-2-(methylsulfanyl)pyrimidin-4(1H)-oneYield 95.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2-methyl-2-thiopseudourea sulfate (Aldrich, 58.74 g, 0.422 mol) in water (1000 mL) were added sodium carbonate (81.44 g, 0.768 mol) and ethyl acetoacetate (50 g, 0.384 mol) at room temperature. The reaction mixture was stirred overnight. After neutralizing to pH=8, the solid was collected through filtration followed by drying under vacuum overnight to afford 6-methyl-2-(methylthio)pyrimidin-4(3H)-one (57.2 g, 95% yield) of product. 1H NMR (400 MHz, DMSO-d6): δ 12.47 (bs, 1H), 5.96 (bs, 1H), 2.47 (s, 3H), 2.17 (s, 3H).

Workup

  1. filtrationthe solid was collected through filtration
  2. customby drying under vacuum overnight

Sources & evidence

ORD record
ord-66b19e3abcc94efc95b36d908e2f0efe
Source dataset
uspto-grants-2013_08
Patent number
US08513266B2

Reaction notes

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