Water → 6-chloro-N-{4-[(1-methyl-1H-benzimidazol-2-yl)oxy]phenyl}-5-nitropyrimidin-4-amine

HRID 1044269

Reaktionsgleichung

Reaktionsgleichung von HRID 1044269
[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[C:3]1[O:11][C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][CH:13]=1.[Cl:19][C:20]1[C:25]([N+:26]([O-:28])=[O:27])=[C:24](Cl)[N:23]=[CH:22][N:21]=1.O>C1COCC1>[Cl:19][C:20]1[N:21]=[CH:22][N:23]=[C:24]([NH:16][C:15]2[CH:17]=[CH:18][C:12]([O:11][C:3]3[N:2]([CH3:1])[C:6]4[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=4[N:4]=3)=[CH:13][CH:14]=2)[C:25]=1[N+:26]([O-:28])=[O:27]

Komponenten

5

Edukt 3

HCID 962WaterHCID 203124,6-Dichloro-5-nitropyrimidineHCID 215636774-[(1-methyl-1H-benzimidazol-2-yl)oxy]aniline

Produkt 1

HCID 585776716-chloro-N-{4-[(1-methyl-1H-benzimidazol-2-yl)oxy]phenyl}-5-nitropyrimidin-4-amineAusbeute 48,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 4-[(1-methyl-1H-benzimidazol-2-yl)oxy]aniline (0.30 g) and TEA (0.26 ml) in THF (15 mL) was added 4,6-dichloro-5-nitropyrimidine (0.24 g) at room temperature, and the mixture was stirred at room temperature for 2 h. The mixture was poured into water, and the mixture was extracted with AcOEt. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography (dry charge, silica gel, eluted with 5%-50% AcOEt in hexane) to give 6-chloro-N-{4-[(1-methyl-1H-benzimidazol-2-yl)oxy]phenyl}-5-nitropyrimidin-4-amine (0.24 g) as a yellow solid.

Aufarbeitung

  1. extractionthe mixture was extracted with AcOEt
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (dry charge, silica gel, eluted with 5%-50% AcOEt in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-9890c5be30c342cca09d6c8496f57d85
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08563575B2

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