(2,4-Dichloro-pyrimidin-5-yl)-(2-methylsulfanyl-pyrimidin-4-yl)-methanol → (2,4-Dichloro-pyrimidin-5-yl)-(2-methylsulfanyl-pyrimidin-4-yl)-methanone

HRID 1809679Notes

Reaction equation

HRID 1809679 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([CH:9]([C:11]2[CH:16]=[CH:15][N:14]=[C:13]([S:17][CH3:18])[N:12]=2)[OH:10])=[CH:4][N:3]=1>ClCCl.CO.O=[Mn]=O>[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([C:9]([C:11]2[CH:16]=[CH:15][N:14]=[C:13]([S:17][CH3:18])[N:12]=2)=[O:10])=[CH:4][N:3]=1

Participants

5

Reactant 1

HCID 86667954(2,4-Dichloro-pyrimidin-5-yl)-(2-methylsulfanyl-pyrimidin-4-yl)-methanol

Product 1

HCID 86667955(2,4-Dichloro-pyrimidin-5-yl)-(2-methylsulfanyl-pyrimidin-4-yl)-methanone

Reagents, catalysts & solvents 3

HCID 14801Manganese dioxideCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (2,4-dichloro-pyrimidin-5-yl)-(2-methylsulfanyl-pyrimidin-4-yl)-methanol (13.6 g, 45 mmol) in dichloromethane (160 mL) and methanol (40 mL) was added MnO2 (55 g, 632 mmol), The mixture was heated at reflux for 16 hours. After cooling to room temperature, the precipitate was removed off by filtration. The filtrate was concentrated and the residue was purified by column chromatography (silica, 20 g, 200-300 mesh, eluting with methanol:dichloromethane, 1:200) to afford (2,4-dichloro-pyrimidin-5-yl)-(2-methylsulfanyl-pyrimidin-4-yl)-methanone. (Yield 9.52 g, 71%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 16 hours
  3. customthe precipitate was removed off by filtration
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified by column chromatography (silica, 20 g, 200-300 mesh, eluting with methanol:dichloromethane, 1:200)

Sources & evidence

ORD record
ord-ba4c096872514981a91589121cf4425a
Source dataset
uspto-grants-2013_01
Patent number
US08362023B2

Reaction notes

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