Ethanol → 3-amino-5,6-dimethyl-2-[3-(4-quinolin-2-ylpiperazin-1-yl)-propylthio]-3H-thieno[2,3-d]pyrimidin-4-one

HRID 1714761

Reaktionsgleichung

Reaktionsgleichung von HRID 1714761
[NH2:1][N:2]1[C:7](=[O:8])[C:6]2[C:9]([CH3:13])=[C:10]([CH3:12])[S:11][C:5]=2[N:4]=[C:3]1[S-:14].[K+].NC1SC(C)=C(C)C=1C(OCC)=O.Cl[CH2:30][CH2:31][CH2:32][N:33]1[CH2:38][CH2:37][N:36]([C:39]2[CH:48]=[CH:47][C:46]3[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=3)[N:40]=2)[CH2:35][CH2:34]1.C(O)C>C(Cl)(Cl)Cl>[NH2:1][N:2]1[C:7](=[O:8])[C:6]2[C:9]([CH3:13])=[C:10]([CH3:12])[S:11][C:5]=2[N:4]=[C:3]1[S:14][CH2:30][CH2:31][CH2:32][N:33]1[CH2:38][CH2:37][N:36]([C:39]2[CH:48]=[CH:47][C:46]3[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=3)[N:40]=2)[CH2:35][CH2:34]1

Komponenten

6

Edukt 4

HCID 702EthanolHCID 78536Ethyl 2-amino-4,5-dimethyl3-thenoateHCID 30355894-(Chloropropyl)-1-(2-quinolyl)piperazineHCID 23701453Potassium 3-amino-5,6-dimethyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-2-thiolate

Produkt 1

HCID 111908233-amino-5,6-dimethyl-2-[3-(4-quinolin-2-ylpiperazin-1-yl)-propylthio]-3H-thieno[2,3-d]pyrimidin-4-oneAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

A mixture of 80 mg of potassium 3-amino-5,6-dimethyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-2-thiolate, which was prepared from ethyl 2-amino-4,5-dimethylthiophene-3-carboxylate; 104 mg of 2-[4-(3-chloropropyl)piperazin-1-yl]quinoline as prepared in the Step 1-1-B; and 5 ml of ethanol, was heated under reflux for 4.5 hours. After cooling off the reaction mixture, chloroform was added, followed by washing with saturated brine. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified on silica gel column chromatography (chloroform:methanol=100: 1) to provide 72 mg (50%) of 3-amino-5,6-dimethyl-2-[3-(4-quinolin-2-ylpiperazin-1-yl)-propylthio]-3H-thieno[2,3-d]pyrimidin-4-one.

Aufarbeitung

  1. temperatureunder reflux for 4.5 hours
  2. additionwas added
  3. washby washing with saturated brine
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified on silica gel column chromatography (chloroform:methanol=100: 1)

Quellen und Nachweise

ORD-Eintrag
ord-cc6cd19d999744c9a3292ecfedcae500
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07799775B2

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