1,4-Dioxane → HCID 11767252, compound

HRID 1082266Notes

Reaction equation

HRID 1082266 reaction equation
Br[C:2]1[C:3]([NH:20][S:21]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([CH3:33])([CH3:32])[CH3:31])=[CH:26][CH:25]=2)(=[O:23])=[O:22])=[N:4][CH:5]=[N:6][C:7]=1[O:8][CH2:9][CH2:10][O:11][C:12]1[N:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][N:13]=1.[CH3:34][O:35][C:36]1[CH:37]=[C:38]([Sn](CCCC)(CCCC)CCCC)[CH:39]=[CH:40][C:41]=1[O:42][CH3:43].O1CCOCC1>C(OCC)(=O)C.[F-].[K+].[Cu]Cl>[C:30]([C:27]1[CH:28]=[CH:29][C:24]([S:21]([NH:20][C:3]2[C:2]([C:39]3[CH:38]=[CH:37][C:36]([O:35][CH3:34])=[C:41]([O:42][CH3:43])[CH:40]=3)=[C:7]([O:8][CH2:9][CH2:10][O:11][C:12]3[N:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][N:13]=3)[N:6]=[CH:5][N:4]=2)(=[O:23])=[O:22])=[CH:25][CH:26]=1)([CH3:33])([CH3:32])[CH3:31]

Participants

7

Reactant 3

HCID 312751,4-DioxaneHCID 10365179Tributyl(3,4-dimethoxyphenyl)stannaneHCID 11071742N-{5-bromo-6-[2-(5-methylthiopyrimidin-2-yloxy)ethoxy]pyrimidin-4-yl}-4-tert-butylbenzenesulfonamide

Product 1

HCID 11767252HCID 11767252, compoundYield 74.3%

Reagents, catalysts & solvents 3

HCID 62652Cuprous chlorideCatalystHCID 8857Ethyl AcetateSolventHCID 522689Potassium FluorideSolvent

Procedure

A mixture of N-{5-bromo-6-[2-(5-methylthiopyrimidin-2-yloxy)ethoxy]pyrimidin-4-yl}-4-tert-butylbenzenesulfonamide (100 mg), 3,4-dimethoxyphenyltributyltin (220 mg), bis(triphenylphsophine)palladium (II) chloride (26 mg), copper (I) chloride (11 mg), a few crystals of 2,6-di-tert-butylcrezol and dioxane (5 ml) is refluxed for 1.5 hour. After cooling, the reaction solution is diluted with ethyl acetate and aqueous potassium fluoride solution, and the mixture is stirred at room temperature for 30 minutes. The insoluble materials are removed by filtration, and the filtrate is acidified with 10% hydrochloric acid, and the mixture is extracted with ethyl acetate. The ethyl acetate layer is washed, dried, and evaporated to remove the solvent. The residue is purified by preparative thin layer chromatography (solvent; chloroform/ethyl acetate=3:1), and recrystallized from ethyl acetate/diisopropyl ether to give 4-tert-butyl-N-{5-(3,4-dimethoxyphenyl)-6-[2-(5-methylthiopyrimidin-2-yloxy)ethoxy]-pyrimidin-4-yl}benzenesulfonamide (82 mg).

Workup

  1. temperatureAfter cooling
  2. customThe insoluble materials are removed by filtration
  3. extractionthe mixture is extracted with ethyl acetate
  4. washThe ethyl acetate layer is washed
  5. customdried
  6. customevaporated
  7. customto remove the solvent
  8. customThe residue is purified by preparative thin layer chromatography (solvent; chloroform/ethyl acetate=3:1)
  9. customrecrystallized from ethyl acetate/diisopropyl ether

Sources & evidence

ORD record
ord-235a6f20ce224342afb89c8ff0642213
Source dataset
uspto-grants-1996_12
Patent number
US05589478

Reaction notes

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