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

https://huagongshe.com/ko/reaction/450545

참여 물질

역할	이름	HCID	투입량
반응물	4-Dimethylaminobutylamine	HCID 77063	—
반응물	Diisopropylethylamine	HCID 81531	—
반응물	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
반응물	4-[4-Fluoro-2-(tetrahydro-pyran-4-yloxy)-phenylamino]-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylic acid methylester	HCID 46182044	—
용매	Dimethylformamide	HCID 6228	—
생성물	N-(4-(Dimethylamino)butyl)-4-(4-fluoro-2-(tetrahydro-2H-pyran-4-yloxy)phenyl-amino)-5-methylthieno[2,3-d]pyrimidine-6-carboxamide	HCID 46182699	37%

반응 조건

온도	0 °C

반응 단계

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%).

출처 및 근거

DOI	10.6084/m9.figshare.5104873.v1
특허 번호	US08486953B2
출처 데이터셋	uspto-grants-2013_07
ORD ID	ord-374d368ce5274b2c89e7276fcc906e99
출처 메모	uspto-grants-2013_07