Bromine → 4-(4-bromo-5-(3,6-dimethyl-2,4-dioxo-1-(3-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydropyrimidin-5-yl)-1H-pyrazol-1-yl)benzonitrile

HRID 576777Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 576777
[CH3:1][N:2]1[C:7](=[O:8])[C:6]([C:9]2[N:13]([C:14]3[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=3)[N:12]=[CH:11][CH:10]=2)=[C:5]([CH3:22])[N:4]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=2)[C:3]1=[O:33].[Br:34]Br.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(O)(=O)C>[Br:34][C:10]1[CH:11]=[N:12][N:13]([C:14]2[CH:15]=[CH:16][C:17]([C:18]#[N:19])=[CH:20][CH:21]=2)[C:9]=1[C:6]1[C:7](=[O:8])[N:2]([CH3:1])[C:3](=[O:33])[N:4]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:30])([F:31])[F:32])[CH:24]=2)[C:5]=1[CH3:22]

Komponenten

5

Edukt 3

HCID 24408BromineHCID 24477Sodium ThiosulfateHCID 712514174-[5-[3,6-dimethyl-2,4-dioxo-1-(3-trifluoromethylphenyl)-1,2,3,4-tetrahydropyrimidin-5-yl]-1H-pyrazol-1-yl]benzonitrile

Produkt 1

HCID 867238984-(4-bromo-5-(3,6-dimethyl-2,4-dioxo-1-(3-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydropyrimidin-5-yl)-1H-pyrazol-1-yl)benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

To a solution of 4-(5-(3,6-dimethyl-2,4-dioxo-1-(3-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydropyrimidin-5-yl)-1H-pyrazol-1-yl)benzonitrile (prepared in Example 1) (665 mg) in acetic acid (15 ml) was added at room temperature bromine (0.75 ml) dropwise and the resulting mixture was stirred at room temperature for fifteen minutes. To the reaction mixture was added 10% aqueous sodium thiosulfate solution (30 ml) and the solids formed were filtered and then washed with hexane (50 ml) and dried under reduced pressure to afford 4-(4-bromo-5-(3,6-dimethyl-2,4-dioxo-1-(3-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydropyrimidin-5-yl)-1H-pyrazol-1-yl)benzonitrile (692.8 mg) as brown solid.

Aufarbeitung

  1. customthe solids formed
  2. filtrationwere filtered
  3. washwashed with hexane (50 ml)
  4. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-82ede62544714ba1ae1a04d00b2e8d0f
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09040516B2

Notizen zur Reaktion

Wird geladen…