Hydrochloric Acid → 4-(3-Aminophenoxy)-N-(4-(4-methylpiperazin-1-yl)phenyl)thieno[3,2-d]pyrimidin-2-amine

HRID 526056Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 526056
Cl.[CH3:2][N:3]1[CH2:8][CH2:7][N:6]([C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]3[N:17]=[C:18]([O:25][C:26]4[CH:31]=[CH:30][CH:29]=[C:28]([N+:32]([O-])=O)[CH:27]=4)[C:19]4[S:24][CH:23]=[CH:22][C:20]=4[N:21]=3)=[CH:11][CH:10]=2)[CH2:5][CH2:4]1>C(O)C.[Fe]>[NH2:32][C:28]1[CH:27]=[C:26]([CH:31]=[CH:30][CH:29]=1)[O:25][C:18]1[C:19]2[S:24][CH:23]=[CH:22][C:20]=2[N:21]=[C:16]([NH:15][C:12]2[CH:11]=[CH:10][C:9]([N:6]3[CH2:5][CH2:4][N:3]([CH3:2])[CH2:8][CH2:7]3)=[CH:14][CH:13]=2)[N:17]=1

Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 68001679N-(4-(4-methylpiperazin-1-yl)phenyl)-4-(3-nitrophenoxy)thieno[3,2-d]pyrimidin-2-amine

Produkt 1

HCID 895474154-(3-Aminophenoxy)-N-(4-(4-methylpiperazin-1-yl)phenyl)thieno[3,2-d]pyrimidin-2-amineAusbeute 67,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysator2×HCID 702EthanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Iron (27.1 mmol) and 12 N HCl aqueous solution (2.17 mmol) were diluted with 50% ethanol aqueous solution (30 mL), followed by stirring at 100° C. for 10 min. The compound (5.42 mmol) obtained in Step 4 was dissolved in 50% ethanol aqueous solution (30 mL) and then added to the reaction flask in which iron was activated, followed by stirring at 100° C. for 1 hour. After the reaction was complete, the reaction mixture was filtered with celite to remove iron, and the filtrate was distilled under a reduced pressure. The residue was distilled with dichloromethane and washed with sat. NaHCO3 aqueous solution. The organic layer was dried with anhydrous sodium sulfate and then filtered and distilled under a reduced pressure. The residue was separated by column chromatography (dichloromethane:methanol=10:1 (volume ratio)) to obtain the title compound (yield: 67.8%).

Aufarbeitung

  1. stirringby stirring at 100° C. for 1 hour
  2. filtrationthe reaction mixture was filtered with celite
  3. customto remove iron
  4. distillationthe filtrate was distilled under a reduced pressure
  5. distillationThe residue was distilled with dichloromethane
  6. washwashed with sat. NaHCO3 aqueous solution
  7. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  8. filtrationfiltered
  9. distillationdistilled under a reduced pressure
  10. customThe residue was separated by column chromatography (dichloromethane:methanol=10:1 (volume ratio))

Quellen und Nachweise

ORD-Eintrag
ord-e3bfc2d4cf504b01812123a204c00906
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09345719B2

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