Phosphorus oxychloride → 2-Chloro-3-methyl-6-(3-fluoropyridin-4-yl)-3H-pyrimidin-4-one

HRID 1091350Notes

Reaction equation

HRID 1091350 reaction equation
P(Cl)(Cl)([Cl:3])=O.[F:6][C:7]1[CH:8]=[N:9][CH:10]=[CH:11][C:12]=1[C:13]1[N:18]=[C:17](S)[N:16]([CH3:20])[C:15](=[O:21])[CH:14]=1>CN(C)C=O>[Cl:3][C:17]1[N:16]([CH3:20])[C:15](=[O:21])[CH:14]=[C:13]([C:12]2[CH:11]=[CH:10][N:9]=[CH:8][C:7]=2[F:6])[N:18]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178481675HCID 178481675, compound

Product 1

HCID 595768122-Chloro-3-methyl-6-(3-fluoropyridin-4-yl)-3H-pyrimidin-4-oneYield 73.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

After one hour stirring of a solution of phosphorus oxychloride (45 g, 293 mmol) in dimethylformamide (450 ml) at room temperature, 6-(3-fluoropyridin-4-yl)-2-mercapto-3-methyl-3H-pyrimidin-4-one (46.3 g, 195 mmol) was added and heated at 60° C. for 2 hours. The resulting suspension was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The aqueous layer was extracted with ethyl acetate and 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-(3-fluoropyridin-4-yl)-3-methyl-3H-pyrimidin-4-one (34.2 g, 143 mmol, 73%) 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-b172098ee8a347979fe670c8cf9740ec
Source dataset
uspto-grants-2012_03
Patent number
US08129377B2

Reaction notes

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