Cornforth reagent → 1-(2,4-Dichloro-6-(2-(isopropylsulfonyl)phenylamino)pyrimidin-5-yl)ethanone

HRID 2046955Notes

Reaction equation

HRID 2046955 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([CH:9]([OH:11])[CH3:10])=[C:4]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[S:19]([CH:22]([CH3:24])[CH3:23])(=[O:21])=[O:20])[N:3]=1.C1C=C[NH+]=CC=1.C1C=C[NH+]=CC=1.[O-][Cr](O[Cr]([O-])(=O)=O)(=O)=O>C(Cl)Cl>[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([C:9](=[O:11])[CH3:10])=[C:4]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[S:19]([CH:22]([CH3:24])[CH3:23])(=[O:21])=[O:20])[N:3]=1

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 582908641-(2,4-Dichloro-6-(2-(isopropylsulfonyl)phenylamino)pyrimidin-5-yl)ethanol

Product 1

HCID 582908761-(2,4-Dichloro-6-(2-(isopropylsulfonyl)phenylamino)pyrimidin-5-yl)ethanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the solution of 1-(2,4-dichloro-6-(2-(isopropylsulfonyl)phenylamino)pyrimidin-5-yl)ethanol (580 mg, 1.49 mmol) in DCM (30 mL) was added PDC (561 mg, 1.49 mmol). The reaction mixture was stirred at room temperature overnight. The reaction mixture was filtered through a pad of silica gel, and the pad was washed by 1 L of DCM. The filtrate was concentrated in vacuo to afford 1-(2,4-dichloro-6-(2-(isopropylsulfonyl)phenylamino)pyrimidin-5-yl)ethanone as a pale yellow solid. MS (ES+): 388.0 (MH+).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of silica gel
  2. washthe pad was washed by 1 L of DCM
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-5a290eadcd6843679478eeadd11adb9b
Source dataset
uspto-grants-2013_11
Patent number
US08592432B2

Reaction notes

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