Potassium Iodide → 6-[2-(1,3,4,5-tetrahydro-2H-pyrido[4,3-b]-indol-2-yl)ethyl]-2,7-dimethyl-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one

HRID 1634188Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1634188
Cl[CH2:2][CH2:3][C:4]1[C:9](=[O:10])[N:8]2[N:11]=[C:12]([CH3:14])[S:13][C:7]2=[N:6][C:5]=1[CH3:15].[CH2:16]1[C:28]2[C:27]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[NH:21][C:20]=2[CH2:19][CH2:18][NH:17]1.C(=O)(O)[O-].[Na+].[I-].[K+]>C(O)CCC>[CH2:16]1[C:28]2[C:27]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[NH:21][C:20]=2[CH2:19][CH2:18][N:17]1[CH2:2][CH2:3][C:4]1[C:9](=[O:10])[N:8]2[N:11]=[C:12]([CH3:14])[S:13][C:7]2=[N:6][C:5]=1[CH3:15]

Komponenten

6

Edukt 4

HCID 4875Potassium IodideHCID 516892Sodium BicarbonateHCID 7232301H,2H,3H,4H,5H-pyrido[4,3-b]indoleHCID 155864606-(2-chloroethyl)-2,7-dimethyl-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one

Produkt 1

HCID 186774246-[2-(1,3,4,5-tetrahydro-2H-pyrido[4,3-b]-indol-2-yl)ethyl]-2,7-dimethyl-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-oneAusbeute 28,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2631-ButanolLösungsmittel

Versuchsvorschrift

A mixture of 6-(2-chloroethyl)-2,7-dimethyl-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one (4.2 g), 1,2,3,4-tetrahydro-5H-pyrido[4,3-b]indole (2.65 g), sodium bicarbonate (2 g), potassium iodide (0.1 g) in 1-butanol (122 ml) was refluxed for 20 hours. The reaction mixture was filtered while hot and the filtrate was evaporated. The residue was purified by column chromatography over silica gel (eluent: CHCl3/CH3OH 95/5). The solvent of the desired fraction was evaporated and the residue was crystallized from acetonitrile, yielding 1.6 g (28.1%) of 6-[2-(1,3,4,5-tetrahydro-2H-pyrido[4,3-b]-indol-2-yl)ethyl]-2,7-dimethyl-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one (compound 42).

Aufarbeitung

  1. temperaturewas refluxed for 20 hours
  2. filtrationThe reaction mixture was filtered while hot and the filtrate
  3. customwas evaporated
  4. customThe residue was purified by column chromatography over silica gel (eluent: CHCl3/CH3OH 95/5)
  5. customThe solvent of the desired fraction was evaporated
  6. customthe residue was crystallized from acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-75d9d18af57b4bf9a4998581fece5a7e
Quelldatensatz
uspto-grants-2003_01
Patentnummer
US06506768B2

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