Phosphorus oxychloride → HCID 86233545, compound

HRID 1091351Notes

Reaction equation

HRID 1091351 reaction equation
P(Cl)(Cl)([Cl:3])=O.[Cl:6][C:7]1[C:12]([Cl:13])=[C:11]([C:14]2[N:19]=[C:18](S)[N:17]([CH3:21])[C:16](=[O:22])[CH:15]=2)[CH:10]=[CH:9][N:8]=1>CN(C)C=O>[Cl:3][C:18]1[N:17]([CH3:21])[C:16](=[O:22])[CH:15]=[C:14]([C:11]2[CH:10]=[CH:9][N:8]=[C:7]([Cl:6])[C:12]=2[Cl:13])[N:19]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 1784816776-(2,3-dichloropyridin-4-yl)-2-mercapto-3-methyl-3H-pyrimidin-4-one

Product 1

HCID 86233545HCID 86233545, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

After one hour stirring of a solution of phosphorus oxychloride (2.9 g, 18.9 mmol) in dimethylformamide (30 ml) at room temperature, 6-(2,3-dichloropyridin-4-yl)-2-mercapto-3-methyl-3H-pyrimidin-4-one (3.58 g, 12.4 mmol) was added and heated at 60° C. for 2 hours. The resulting suspension was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate and the aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with brine, dried over magnesium sulfate, and concentrated in vacuo. The residue was washed by hexane to furnish 2-chloro-6-(2,3-dichloropyridin-4-yl)-3-methyl-3H-pyrimidin-4-one (2.6 g, 8.95 mmol, 72%) as white crystals.

Workup

  1. customThe resulting suspension was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. washThe residue was washed by hexane

Sources & evidence

ORD record
ord-f56536f0af64418e9c225498fbd32d2f
Source dataset
uspto-grants-2012_03
Patent number
US08129377B2

Reaction notes

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