Selenium Dioxide → 4-tert-butyl-N-[5-(2-chloro-5-methoxy-phenoxy)-6-formyl-2-(morpholin-4-yl)-pyrimidin-4-yl]-benzenesulphonamide

HRID 37093

Reaction equation

HRID 37093 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[C:20]([O:21][C:22]3[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:23]=3[Cl:30])=[C:19]([CH3:31])[N:18]=[C:17]([N:32]3[CH2:37][CH2:36][O:35][CH2:34][CH2:33]3)[N:16]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[Se](=O)=[O:39]>O1CCOCC1>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[C:20]([O:21][C:22]3[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:23]=3[Cl:30])=[C:19]([CH:31]=[O:39])[N:18]=[C:17]([N:32]3[CH2:33][CH2:34][O:35][CH2:36][CH2:37]3)[N:16]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 24007Selenium DioxideHCID 199347354-tert-butyl-N-[5-(2-chloro-5-methoxy-phenoxy)-6-methyl-2-(morpholin-4-yl)-pyrimidin-4-yl]-benzenesulphonamide

Product 1

HCID 199347764-tert-butyl-N-[5-(2-chloro-5-methoxy-phenoxy)-6-formyl-2-(morpholin-4-yl)-pyrimidin-4-yl]-benzenesulphonamideYield 68.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

14.6 g of 4-tert-butyl-N-[5-(2-chloro-5-methoxy-phenoxy)-6-methyl-2-(morpholin-4-yl)-pyrimidin-4-yl]-benzenesulphonamide and 15.9 g of selenium dioxide in 500 ml of dioxan were stirred in an autoclave at 170° C. for 6 hours. The reaction mixture was filtered and the filtrate was concentrated. The residue was partitioned between chloroform and water. The organic phase was dried, the solvent was evaporated and the residue was recrystallized from dichloromethane-ethanol. There were obtained 10.3 g of 4-tert-butyl-N-[5-(2-chloro-5-methoxy-phenoxy)-6-formyl-2-(morpholin-4-yl)-pyrimidin-4-yl]-benzenesulphonamide, m.p. 235°-236° C., MS: M=561.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customThe residue was partitioned between chloroform and water
  4. customThe organic phase was dried
  5. customthe solvent was evaporated
  6. customthe residue was recrystallized from dichloromethane-ethanol

Sources & evidence

ORD record
ord-0984aa4c68da44cc8dee59e8886ce9f0
Source dataset
uspto-grants-1995_05
Patent number
US05420129

Linked notes

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