Potassium Carbonate → 4-tert-butyl-N-[5-(3-methoxyphenoxy)-6-{2-(2-pyrimidinylamino)ethoxy}-pyrimidin-4-yl]benzenesulfonamide hydrate

HRID 1082262

Reaktionsgleichung

Reaktionsgleichung von HRID 1082262
Cl.[NH2:2][CH2:3][CH2:4][O:5][C:6]1[N:11]=[CH:10][N:9]=[C:8]([NH:12][S:13]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:18][CH:17]=2)(=[O:15])=[O:14])[C:7]=1[O:26][C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([O:33][CH3:34])[CH:28]=1.Cl[C:36]1[N:41]=[CH:40][CH:39]=[CH:38][N:37]=1.C(=O)([O-])[O-].[K+].[K+].CC(N(C)C)=O>[Cl-].[NH4+]>[OH2:5].[C:22]([C:19]1[CH:18]=[CH:17][C:16]([S:13]([NH:12][C:8]2[C:7]([O:26][C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([O:33][CH3:34])[CH:28]=3)=[C:6]([O:5][CH2:4][CH2:3][NH:2][C:36]3[N:41]=[CH:40][CH:39]=[CH:38][N:37]=3)[N:11]=[CH:10][N:9]=2)(=[O:15])=[O:14])=[CH:21][CH:20]=1)([CH3:25])([CH3:24])[CH3:23]

Komponenten

6

Edukt 4

HCID 11430Potassium CarbonateHCID 31374DimethylacetamideHCID 744042-ChloropyrimidineHCID 67654095N-{6-(2-aminoethoxy)-5-(3-methoxyphenoxy)pyrimidin-4-yl}-4-tert-butylbenzenesulfonamide hydrochloride

Produkt 1

HCID 196894824-tert-butyl-N-[5-(3-methoxyphenoxy)-6-{2-(2-pyrimidinylamino)ethoxy}-pyrimidin-4-yl]benzenesulfonamide hydrateAusbeute 161,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 25517Ammonium ChlorideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of Compound A (150 mg), 2-chloropyrimidine (61 mg), potassium carbonate (122 mg) and dimethylacetamide (1.5 ml) is heated with stirring at 100° C. for three days. The reaction solution is diluted with aqueous ammonium chloride solution, and extracted with ethyl acetate. The extract is washed and dried. The solvent is evaporated to remove the solvent, and the residue is purified by silica gel column chromatography (solvent; chloroform/methanol =100:1) and further recrystallized from ethyl acetate/n-hexane to give 4-tert-butyl-N-[5-(3-methoxyphenoxy)-6-{2-(2-pyrimidinylamino)ethoxy}-pyrimidin-4-yl]benzenesulfonamide hydrate (135 mg) as crystals.

Aufarbeitung

  1. temperatureis heated
  2. extractionextracted with ethyl acetate
  3. washThe extract is washed
  4. customdried
  5. customThe solvent is evaporated
  6. customto remove the solvent
  7. customthe residue is purified by silica gel column chromatography (solvent; chloroform/methanol =100:1)
  8. customfurther recrystallized from ethyl acetate/n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-bdcd16175ec840488b5a139991da87b5
Quelldatensatz
uspto-grants-1996_12
Patentnummer
US05589478

Verknüpfte Notizen

Wird geladen…