2,4,6-Trichloro-5-pyrimidinecarboxaldehyde → 2,4-Dichloro-6-(2-(isopropylsulfonyl)phenylamino)pyrimidine-5-carbaldehyde

HRID 2046953Notes

Reaction equation

HRID 2046953 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([CH:9]=[O:10])=[C:4]([Cl:11])[N:3]=1.[CH:12]([S:15]([C:18]1[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=1[NH2:20])(=[O:17])=[O:16])([CH3:14])[CH3:13]>C(Cl)Cl>[Cl:1][C:2]1[N:3]=[C:4]([Cl:11])[C:5]([CH:9]=[O:10])=[C:6]([NH:20][C:19]2[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=2[S:15]([CH:12]([CH3:14])[CH3:13])(=[O:17])=[O:16])[N:7]=1

Participants

4

Reactant 2

HCID 109327462,4,6-Trichloro-5-pyrimidinecarboxaldehydeHCID 126463662-(Propane-2-sulfonyl)aniline

Product 1

HCID 582908822,4-Dichloro-6-(2-(isopropylsulfonyl)phenylamino)pyrimidine-5-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2,4,6-trichloropyrimidine-5-carbaldehyde (5.0 g, 23.8 mmol) in DCM (50 mL) was added 2-(isopropylsulfonyl)aniline (9.5 g, 47.6 mmol) at 0° C. under nitrogen atmosphere. The reaction mixture was warmed to room temperature gradually and stirred overnight. The solid was filtered off, and the filtrate was concentrated in vacuo and purified by silica gel chromatography (DCM/EtOAC/Hexanes: 15/15/70) to afford 2,4-dichloro-6-(2-(isopropylsulfonyl)phenylamino)pyrimidine-5-carbaldehyde. MS (ES+): 374.0 (MH+).

Workup

  1. filtrationThe solid was filtered off
  2. concentrationthe filtrate was concentrated in vacuo
  3. custompurified by silica gel chromatography (DCM/EtOAC/Hexanes: 15/15/70)

Sources & evidence

ORD record
ord-a2b30f1918e946c59021ddf60f589139
Source dataset
uspto-grants-2013_11
Patent number
US08592432B2

Reaction notes

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