Phosphorus oxychloride → 4-Chloro-2-methylthio-6-(3-trifluoromethyl-phenyl)-pyrimidine

HRID 2053086Notes

Reaction equation

HRID 2053086 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[C:7](O)[CH:6]=[C:5]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)[N:4]=1.P(Cl)(Cl)([Cl:22])=O>>[Cl:22][C:7]1[CH:6]=[C:5]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)[N:4]=[C:3]([S:2][CH3:1])[N:8]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 1785035332-methylsulfanyl-6-[3-(trifluoromethyl)phenyl]-1H-pyrimidin-4-one

Product 1

HCID 866125004-Chloro-2-methylthio-6-(3-trifluoromethyl-phenyl)-pyrimidine

Procedure

2-Methylsulfanyl-6-(3-trifluoromethyl-phenyl)-pyrimidin-4-ol (500 mg) and phosphorous oxychloride (2.5 ml) were heated to reflux for four hours. The reaction mixture was concentrated under reduced pressure and the remaining residue dissolved in ethyl acetate (50 ml) and washed with water (2×30 ml). Organics were separated, dried over sodium sulphate and solvent was removed under reduced pressure to yield 4-chloro-2-methylsulfanyl-6-(3-trifluoromethyl-phenyl)-pyrimidine (478 mg) as a brown solid.

Workup

  1. temperatureto reflux for four hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutionthe remaining residue dissolved in ethyl acetate (50 ml)
  4. washwashed with water (2×30 ml)
  5. customOrganics were separated
  6. dry with materialdried over sodium sulphate and solvent
  7. customwas removed under reduced pressure

Sources & evidence

ORD record
ord-74c261d3192a46d1940be3c02b122c40
Source dataset
uspto-grants-2008_02
Patent number
US07326715B2

Reaction notes

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