(2-Chlorophenyl)-(4,6-dichloro-2-methylsulfanylpyrimidin-5-yl)-methanol → (2-Chlorophenyl)-(4,6-dichloro-2-methylsulfanylpyrimidin-5-yl)-methanone

HRID 2114547Notes

Reaction equation

HRID 2114547 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([C:10]1[C:11]([Cl:19])=[N:12][C:13]([S:17][CH3:18])=[N:14][C:15]=1[Cl:16])[OH:9]>C1(C)C=CC=CC=1.[O-2].[Mn+4].[O-2]>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([C:10]1[C:11]([Cl:19])=[N:12][C:13]([S:17][CH3:18])=[N:14][C:15]=1[Cl:16])=[O:9]

Participants

4

Reactant 1

HCID 59812918(2-Chlorophenyl)-(4,6-dichloro-2-methylsulfanylpyrimidin-5-yl)-methanol

Product 1

HCID 59812853(2-Chlorophenyl)-(4,6-dichloro-2-methylsulfanylpyrimidin-5-yl)-methanoneYield 16.3%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolvent

Procedure

To a solution of (2-chlorophenyl)-(4,6-dichloro-2-methylsulfanylpyrimidin-5-yl)-methanol (8.6 g, 25.6 mmol) in toluene (300 mL) was added manganese (IV) oxide (Aldrich) (22.3 g, 10 eq), and the resulting mixture was heated to reflux with stirring for a total of 5 hours. The reaction was cooled to room temperature and then filtered through a 3.5 cm pad of Celite and the filtrate was concentrated to give 8.84 g of a crude product. Purification by Flash Column Chromatography on Silica Gel eluting with a gradient starting with pure hexanes and progressing to 2% ethyl acetate in hexanes and finally 5% ethyl acetate in hexanes gave the title compound as an off-white powder (1.388 g, (M+H)+=333).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux
  3. filtrationfiltered through a 3.5 cm pad of Celite
  4. concentrationthe filtrate was concentrated
  5. customto give 8.84 g of a crude product
  6. customPurification by Flash Column Chromatography on Silica Gel eluting with a gradient

Sources & evidence

ORD record
ord-60c5acc5e7494ce4acbe164e0b01ef1b
Source dataset
uspto-grants-2008_10
Patent number
US07435731B2

Reaction notes

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