Phosphorus oxychloride → 4-Chloro-5-methyl-2-(methylthio)pyrimidine

HRID 1514406Notes

Reaction equation

HRID 1514406 reaction equation
[CH3:1][C:2]1[C:3](=O)[NH:4][C:5]([S:8][CH3:9])=[N:6][CH:7]=1.O=P(Cl)(Cl)[Cl:13]>O1CCOCC1>[Cl:13][C:3]1[C:2]([CH3:1])=[CH:7][N:6]=[C:5]([S:8][CH3:9])[N:4]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 2405755-Methyl-2-(methylthio)pyrimidin-4(3H)-one

Product 1

HCID 235627084-Chloro-5-methyl-2-(methylthio)pyrimidineYield 89%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 5-methyl-2-methylsulfanyl-3H-pyrimidin-4-one (6.86 g, 44 mmol) and POCl3 (14 ml) in dioxane (60 ml) was refluxed for 2 hours. The solvent was removed under vacuum and the residue was quenched with ice and extracted with diethylether. The organic phase was dried (Na2SO4) and evaporated to give 6.8 g of the title compound as oil that was used in the next step without further purification. (89% yield)

Workup

  1. temperaturewas refluxed for 2 hours
  2. customThe solvent was removed under vacuum
  3. customthe residue was quenched with ice
  4. extractionextracted with diethylether
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-3d097722860d4ba3a29d4cf7f1820570
Source dataset
uspto-grants-2012_07
Patent number
US08222266B2

Reaction notes

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