2-Methyl-2-thiopseudourea sulfate → 4-Trifluoromethyl-2-methylthio-6-(pyridin-2-yl)pyrimidine

HRID 1091630Notes

Reaction equation

HRID 1091630 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3](=O)[CH2:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1)=O.S(O)(O)(=O)=O.[CH3:21][S:22][C:23](=[NH:25])[NH2:24].[O-]CC.[Na+]>C(O)C>[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)[N:25]=[C:23]([S:22][CH3:21])[N:24]=1

Participants

5

Reactant 3

HCID 752702-Methyl-2-thiopseudourea sulfateHCID 2723922Sodium ethoxideHCID 27714784,4,4-Trifluoro-1-(pyridin-2-yl)butane-1,3-dione

Product 1

HCID 665932924-Trifluoromethyl-2-methylthio-6-(pyridin-2-yl)pyrimidineYield 17%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4,4,4-trifluoro-1-(pyridin-2-yl)butane-1,3-dione (1.0 g, 4.6 mmol) in ethanol (10 mL) was added 2-methyl-2-thiopseudourea sulfate (0.64 g, 4.6 mmol), followed by sodium ethoxide (3.0 mL of 21 wt. % solution in ethanol, 9 mmol). The mixture was heated at reflux for 9 h, then cooled to room temperature and extracted with EA. The EA was washed with water and the solvent removed under reduced pressure. The crude product was purified by column chromatography, eluting with 49:1 chloroform/MeOH, to give 4-trifluoromethyl-2-methylthio-6-(pyridin-2-yl)pyrimidine (0.21 g, 17% yield) as an off-white solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 9 h
  3. extractionextracted with EA
  4. washThe EA was washed with water
  5. customthe solvent removed under reduced pressure
  6. customThe crude product was purified by column chromatography
  7. washeluting with 49:1 chloroform/MeOH

Sources & evidence

ORD record
ord-df5cfb85256343b4a98440a4d2463762
Source dataset
uspto-grants-2012_03
Patent number
US08129396B2

Reaction notes

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