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

온도

0 °C

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%).

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)

ORD 기록

ord-374d368ce5274b2c89e7276fcc906e99

출처 데이터셋

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08486953B2