2-Chloro-N,N-dimethylpyrimidin-4-amine → 4-Amino-6,7-dimethoxy-2-[4-(4-dimethylaminopyrimidin-2-yl)piperazin-1-yl]quinoline dihydrochloride dihydrate

HRID 542207

Reaktionsgleichung

Reaktionsgleichung von HRID 542207
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[C:4]([N:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[CH:3]=1.[Cl:22][C:23]1[N:28]=[C:27]([N:29]([CH3:31])[CH3:30])[CH:26]=[CH:25][N:24]=1>C(O)CCC>[OH2:12].[OH2:12].[ClH:22].[ClH:22].[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[C:4]([N:16]2[CH2:17][CH2:18][N:19]([C:23]3[N:28]=[C:27]([N:29]([CH3:31])[CH3:30])[CH:26]=[CH:25][N:24]=3)[CH2:20][CH2:21]2)[CH:3]=1

Komponenten

4

Edukt 2

HCID 959752-Chloro-N,N-dimethylpyrimidin-4-amineHCID 140689984-Amino-6,7-dimethoxy-2-(piperazin-1-yl)quinoline

Produkt 1

HCID 201311224-Amino-6,7-dimethoxy-2-[4-(4-dimethylaminopyrimidin-2-yl)piperazin-1-yl]quinoline dihydrochloride dihydrateAusbeute 25,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2631-ButanolLösungsmittel

Versuchsvorschrift

4-Amino-6,7-dimethoxy-2-(piperazin-1-yl)quinoline (1.26 g) and 2-chloro-4-dimethylaminopyrimidine (0.76 g) in n-butanol (60 ml) were heated under reflux for 16 hours. The mixture was then evaporated in vacuo, the residue partitioned between chloroform and sodium carbonate solution (10%) and the aqueous phase extracted with chloroform. The combined extracts were washed with water, dried (Na2SO4), evaporated in vacuo and the residue chromatographed on silica gel (Merck 9385). Elution with chloroform-methanol (100:0→95.5) followed by treatment of the product with ethereal hydrogen chloride and recrystallisation from methanol gave 4-amino-6,7-dimethoxy-2-[4-(4-dimethylaminopyrimidin-2-yl)piperazin-1-yl]quinoline dihydrochloride dihydrate (0.19 g), m.p. 260°-263°.

Aufarbeitung

  1. temperatureunder reflux for 16 hours
  2. customThe mixture was then evaporated in vacuo
  3. customthe residue partitioned between chloroform and sodium carbonate solution (10%)
  4. extractionthe aqueous phase extracted with chloroform
  5. washThe combined extracts were washed with water
  6. dry with materialdried (Na2SO4)
  7. customevaporated in vacuo
  8. customthe residue chromatographed on silica gel (Merck 9385)
  9. washElution with chloroform-methanol (100:0→95.5)
  10. customfollowed by treatment of the product with ethereal hydrogen chloride and recrystallisation from methanol

Quellen und Nachweise

ORD-Eintrag
ord-e68641a975ef4ed6a4a47b8e4d03dbc1
Quelldatensatz
uspto-grants-1987_04
Patentnummer
US04656174

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