4-Iodo-2-(methylthio)pyrimidine → 2-(4-Fluorophenyl)-1-(2-methylthio-4-pyrimidinyl)-5-(4-tert.butoxycarbonyl-1-piperazinyl)imidazo[4,5-b]pyridine

HRID 396379Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 396379
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10]3[C:11]([N:29]=2)=[N:12][C:13]([N:16]2[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]2)=[CH:14][CH:15]=3)=[CH:4][CH:3]=1.I[C:31]1[CH:36]=[CH:35][N:34]=[C:33]([S:37][CH3:38])[N:32]=1>C1(C)C=CC=CC=1.CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]([C:31]3[CH:36]=[CH:35][N:34]=[C:33]([S:37][CH3:38])[N:32]=3)[C:10]3[C:11]([N:29]=2)=[N:12][C:13]([N:16]2[CH2:17][CH2:18][N:19]([C:22]([O:24][C:25]([CH3:26])([CH3:28])[CH3:27])=[O:23])[CH2:20][CH2:21]2)=[CH:14][CH:15]=3)=[CH:6][CH:7]=1

Komponenten

5

Edukt 2

HCID 38589014-Iodo-2-(methylthio)pyrimidineHCID 224861362-(4-Fluorophenyl)-5-(4-tert.butoxycarbonyl-1-piperazinyl)imidazo[4,5-b]pyridine

Produkt 1

HCID 224861592-(4-Fluorophenyl)-1-(2-methylthio-4-pyrimidinyl)-5-(4-tert.butoxycarbonyl-1-piperazinyl)imidazo[4,5-b]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittel2×HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

KN(TMS)2 (812 mg, 3.85 mmol) in toluene (3.85 ml) is added at 0° C. to a solution of 2-(4-Fluorophenyl)-5-(4-tert.butoxycarbonyl-1-piperazinyl)imidazo[4,5-b]pyridine (1.4 g, 3.5 mmol) in DMF (7 ml). After stirring at room temperature for 30 min., 4-iodo-2-methylthiopyrimidine (970 mg, 3.85 mmol) in toluene (3.85 ml) is added and the reaction stirred at room temperature for 1 h. Toluene is evaporated, the reaction mixture heated to 120° C. for 18 h, poured on water and extracted with ethyl acetate (containing 5% EtOH) three times. The combined organic phases are washed with brine, dried over Na2SO4, filtered and evaporated to dryness. Purification over SiO2 (acetone/hexanes 20/80) renders the title compound (950 mg, 52%) as colorless foam.

Aufarbeitung

  1. stirringthe reaction stirred at room temperature for 1 h
  2. customToluene is evaporated
  3. temperaturethe reaction mixture heated to 120° C. for 18 h
  4. additionpoured on water
  5. extractionextracted with ethyl acetate (containing 5% EtOH) three times
  6. washThe combined organic phases are washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customevaporated to dryness
  10. customPurification over SiO2 (acetone/hexanes 20/80)

Quellen und Nachweise

ORD-Eintrag
ord-3967eb77de6a4aa9bf3b874a7ba6a0b7
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06608072B1

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