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Piperazine → 2-(1-pyperazinyl)-4-(3-chloro-4-methoxybenzylamino)-5-[N-(2-pyridylmethyl)carbamoyl] pyrimidine

HRID 1352740
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1352740
CS[C:3]1[N:8]=[C:7]([NH:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([Cl:19])[CH:12]=2)[C:6]([C:20](=[O:29])[NH:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=2)=[CH:5][N:4]=1.ClC1C=CC=C(C(OO)=O)C=1.[NH:41]1[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]1.C(OCC)(=O)C>C(Cl)(Cl)Cl>[N:41]1([C:3]2[N:8]=[C:7]([NH:9][CH2:10][C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([Cl:19])[CH:12]=3)[C:6]([C:20](=[O:29])[NH:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)=[CH:5][N:4]=2)[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 4837PiperazineHCID 8857Ethyl AcetateHCID 70297m-Chloroperbenzoic acidHCID 17848351HCID 17848351, Verbindung

Produkt 1

HCID 692686192-(1-pyperazinyl)-4-(3-chloro-4-methoxybenzylamino)-5-[N-(2-pyridylmethyl)carbamoyl] pyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212
Chloroform
Lösungsmittel

Versuchsvorschrift

A solution of 2-methylthio-4-(3-chloro-4-methoxybenzylamino)-5-[N-(2-pyridylmethyl)carbamoyl]pyrimidine (prepared in Example 80) 150.0 mg in chloroform 5.0 ml is treated with m-chloroperbenzoic acid (80%) 85.6 mg at 0° C. for 30 minites. Piperazine 0.263 g is added thereto and the mixture is stirred at room temperature overnight. To the reaction mixture is added ethyl acetate and an aqueous saturated sodium hydrogen carbonate solution, and the organic layer is separated. The organic layer is washed with an aqueous saturated sodium hydrogen carbonate solution, water and a saturated brine, dried over anhydrous sodium sulfate, filtered and then concentrated in vacuo. The residue is purified with silica gel chromatography (solvent; ethyl acetate) to give 2-(1-pyperazinyl)-4-(3-chloro-4-methoxybenzylamino)-5-[N-(2-pyridylmethyl)carbamoyl]pyrimidine as a colorless amorphous solid, 128.4 mg.

Aufarbeitung

  1. customan aqueous saturated sodium hydrogen carbonate solution, and the organic layer is separated
  2. washThe organic layer is washed with an aqueous saturated sodium hydrogen carbonate solution, water
  3. dry with materiala saturated brine, dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified with silica gel chromatography (solvent; ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-83b0bb95e9c94bdba3b40687133dc544
Quelldatensatz
uspto-grants-2007_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07220736B2

Notizen zur Reaktion

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