HCID 59834305, compound → HCID 59834315, compound

HRID 230127Notes

Reaction equation

HRID 230127 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:18])=[N:12][C:13]([S:16][CH3:17])=[N:14][CH:15]=1)[OH:9]>C1(C)C=CC=CC=1.[O-2].[Mn+4].[O-2]>[Cl:18][C:11]1[C:10]([C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])=[O:9])=[CH:15][N:14]=[C:13]([S:16][CH3:17])[N:12]=1

Participants

4

Reactant 1

HCID 59834305HCID 59834305, compound

Product 1

HCID 59834315HCID 59834315, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolvent

Procedure

To a solution of (2-chlorophenyl)-(4-chloro-2-methylsulfanylpyrimidin-5-yl)methanol (10.8 g, 35.75 mmol) in toluene (150 mL) was added manganese (IV) oxide (Aldrich) (31.2 g, 10 eq). The resulting mixture was heated to reflux with stirring for a total of 2.5 hours. The reaction was then filtered hot through a 3.5 cm pad of Celite. The pad of Celite was rinsed with hot ethyl acetate, and the filtrate was concentrated to give a crude oil. Purification by Flash Column Chromatography on Silica Gel eluting with a gradient of 2%-10% ethyl acetate in hexanes gave the title compound as a yellow viscous semi-solid (5.3 g, (M+H)+=299.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux
  3. filtrationThe reaction was then filtered hot through a 3.5 cm pad of Celite
  4. washThe pad of Celite was rinsed with hot ethyl acetate
  5. concentrationthe filtrate was concentrated
  6. customto give a crude oil
  7. customPurification by Flash Column Chromatography on Silica Gel eluting with a gradient of 2%-10% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-b19eda1ea03d493496c5da3b3d0a9b8c
Source dataset
uspto-grants-2009_07
Patent number
US07566708B2

Reaction notes

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