Phosphorus oxychloride → 4-Chloro-5,6-diphenyl-2-(trifluoromethyl)pyrimidine

HRID 2250329Notes

Reaction equation

HRID 2250329 reaction equation
[C:1]1([C:7]2[C:8](=O)[NH:9][C:10]([C:19]([F:22])([F:21])[F:20])=[N:11][C:12]=2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)(O)[O-].[Na+].P(Cl)(Cl)([Cl:31])=O>>[Cl:31][C:8]1[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:11]=[C:10]([C:19]([F:22])([F:21])[F:20])[N:9]=1

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 1355286295,6-Diphenyl-2-(trifluoromethyl)pyrimidin-4(3H)-one

Product 1

HCID 104046804-Chloro-5,6-diphenyl-2-(trifluoromethyl)pyrimidineYield 76.6%

Procedure

5,6-Diphenyl-2-(trifluoromethyl)pyrimidin-4(3H)-one (8.0 g, 25 mmol) (synthesized according to the procedure described in our PCT application No. IB03/01289) was refluxed in phosphorus oxychloride (15 ml) for 5 hours and allowed to cool to room temperature. The reaction mixture was poured onto ice-water mixture and neutralised with saturated sodium bicarbonate solution. The solid thus separated was extracted with dichloromethane. The organic extract was washed with water, dried over anhydrous sodium sulphate and concentrated under reduced pressure to give crude product, which was purified by column chromatography to afford the title compound (6.5 g, 76.6%, HPLC purity 99.8%), mp: 105-107° C.

Workup

  1. customThe solid thus separated
  2. extractionwas extracted with dichloromethane
  3. extractionThe organic extract
  4. washwas washed with water
  5. dry with materialdried over anhydrous sodium sulphate
  6. concentrationconcentrated under reduced pressure
  7. customto give crude product, which
  8. customwas purified by column chromatography

Sources & evidence

ORD record
ord-f726b082c30d47999ad64adf56da2349
Source dataset
uspto-grants-2008_01
Patent number
US07317014B2

Reaction notes

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