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

HRID 2046986Notes

Reaction equation

HRID 2046986 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([CH:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[OH:10])=[C:4]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[S:24]([CH:27]([CH3:29])[CH3:28])(=[O:26])=[O:25])[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]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[O:10])=[C:4]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[S:24]([CH:27]([CH3:29])[CH3:28])(=[O:26])=[O:25])[N:3]=1

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 58290857(2,4-Dichloro-6-(2-(isopropylsulfonyl)phenylamino)pyrimidin-5-yl)(phenyl)methanol

Product 1

HCID 58290891(2,4-Dichloro-6-(2-(isopropylsulfonyl)phenylamino)pyrimidin-5-yl)(phenyl)methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the solution of (2,4-dichloro-6-(2-(isopropylsulfonyl)phenylamino)pyrimidin-5-yl)(phenyl)methanol (113.4 mg, 0.25 mmol) in DCM (10 mL) was added PDC (236 mg, 0.63 mmol). The reaction mixture was stirred at room temperature overnight. The resulting mixture was then filtered through a pad of silica gel, and the pad was washed by 5% EtOAc in DCM (200 mL). The filtrate was concentrated in vacuo to afford (2,4-dichloro-6-(2-(isopropylsulfonyl)phenylamino)pyrimidin-5-yl)(phenyl)methanone as a colorless oil. MS (ES+): 450.0 (MH+).

Workup

  1. filtrationThe resulting mixture was then filtered through a pad of silica gel
  2. washthe pad was washed by 5% EtOAc in DCM (200 mL)
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-ab2b4bd584b34282a82a3e058ffa7bcc
Source dataset
uspto-grants-2013_11
Patent number
US08592432B2

Reaction notes

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