4-Dimethylaminobutylamine → N-(4-(Dimethylamino)butyl)-4-(4-fluoro-2-(tetrahydro-2H-pyran-4-yloxy)phenyl-amino)-5-methylthieno[2,3-d]pyrimidine-6-carboxamide

HRID 450545

Reaktionsgleichung

Reaktionsgleichung von HRID 450545
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[F:25][C:26]1[CH:31]=[CH:30][C:29]([NH:32][C:33]2[C:34]3[C:41]([CH3:42])=[C:40]([C:43](OC)=[O:44])[S:39][C:35]=3[N:36]=[CH:37][N:38]=2)=[C:28]([O:47][CH:48]2[CH2:53][CH2:52][O:51][CH2:50][CH2:49]2)[CH:27]=1.CCN(C(C)C)C(C)C.[CH3:63][N:64]([CH3:70])[CH2:65][CH2:66][CH2:67][CH2:68][NH2:69]>CN(C=O)C>[CH3:63][N:64]([CH3:70])[CH2:65][CH2:66][CH2:67][CH2:68][NH:69][C:43]([C:40]1[S:39][C:35]2[N:36]=[CH:37][N:38]=[C:33]([NH:32][C:29]3[CH:30]=[CH:31][C:26]([F:25])=[CH:27][C:28]=3[O:47][CH:48]3[CH2:49][CH2:50][O:51][CH2:52][CH2:53]3)[C:34]=2[C:41]=1[CH3:42])=[O:44]

Komponenten

6

Edukt 4

HCID 770634-DimethylaminobutylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 461820444-[4-Fluoro-2-(tetrahydro-pyran-4-yloxy)-phenylamino]-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylic acid methylester

Produkt 1

HCID 46182699N-(4-(Dimethylamino)butyl)-4-(4-fluoro-2-(tetrahydro-2H-pyran-4-yloxy)phenyl-amino)-5-methylthieno[2,3-d]pyrimidine-6-carboxamideAusbeute 37 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

HATU (0.073 g, 0.193 mmol) was added into a mixture of methyl 4-(4-fluoro-2-(tetrahydro-2H-pyran-4-yloxy)phenylamino)-5-methylthieno[2,3-d]pyrimidine-6-carboxylate (0.07 g, 0.175 mmol) and Hünig's base (30 μL, 0.175 mmol) in DMF (2.0 mL) at 0° C. The reaction mixture was stirred at 0° C. for 0.5 hours. N1,N1-dimethylbutane-1,4-diamine (0.177 g, 0.875 mmol) was added, the coolant removed and the reaction stirred at ambient temperature overnight. The crude reaction mixture was applied to an SCX cartridge and eluted with MeOH (30 mL) followed by ammonia in MeOH. The product was purified by flash column chromatography (10% MeOH/DCM→15% MeOH/DCM/0.5% NH4OH) to give the title compound as a waxy colourless solid (0.012 g, 37%).

Aufarbeitung

  1. customthe coolant removed
  2. stirringthe reaction stirred at ambient temperature overnight
  3. customThe crude reaction mixture
  4. washeluted with MeOH (30 mL)
  5. customThe product was purified by flash column chromatography (10% MeOH/DCM→15% MeOH/DCM/0.5% NH4OH)

Quellen und Nachweise

ORD-Eintrag
ord-374d368ce5274b2c89e7276fcc906e99
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08486953B2

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