1,3-二氢噻吩并[3,2-d]嘧啶-2,4-二酮合成路线 （共 20 条）
反应条件
1: 97 percent / bromine / acetic acid / 48 h / 110 °C 2: 64 percent / POCl3; N,N-diethylaniline / 3 h / Heating View Scheme
参考文献
CURIS, INC.; BAO, Rudi; LAI, Chengjung; QIAN, Changgeng
Patent: WO2011/130628 A1, 2011 ;
WO 2011/130628 A1
反应条件
1.1: trichlorophosphate / 10 h / Reflux 2.1: methanol / 1 h / 20 °C 3.1: lithium diisopropyl amide / hexane; tetrahydrofuran / 1 h / -78 °C 3.2: 11 h / -78 - 20 °C View Scheme
参考文献
Zhu, Wufu; Zhai, Xin; Fu, Qiangqiang; Guo, Fei; Bai, Mei; Wang, Jianqiang; Wang, Haiyan; Gong, Ping
Chemical and Pharmaceutical Bulletin, 2012 , vol. 60, # 8 p. 1037 - 1045
反应条件
1.1: trichlorophosphate / 10 h / Reflux 2.1: methanol / 1 h / 20 °C 3.1: lithium diisopropyl amide / hexane; tetrahydrofuran / 1 h / -78 °C 3.2: 11 h / -78 - 20 °C 4.1: titanium(IV) isopropylate; triethylamine / chloroform / Reflux 4.2: 12 h / 20 °C 5.1: sodium hydrogencarbonate / bis-triphenylphosphine-palladium(II) chloride / toluene; ethanol; water / 1 h / 120 °C / Inert atmosphere; Microwave irradiation View Scheme
参考文献
WO2011/130628 A1, ;
WO 2011/130628 A1
反应条件
1: trichlorophosphate / acetonitrile / 48 h / Reflux 2: 10 palladium on activated charcoal; hydrogen; sodium carbonate / ethanol / 24 h / 20 °C View Scheme
参考文献
Temburnikar, Kartik W.; Zimmermann, Sarah C.; Kim, Nathaniel T.; Ross, Christina R.; Gelbmann, Christopher; Salomon, Christine E.; Wilson, Gerald M.; Balzarini, Jan; Seley-Radtke, Katherine L.
Bioorganic and Medicinal Chemistry, 2014 , vol. 22, # 7 p. 2113 - 2122
反应条件
N-ethyl-N,N-diisopropylamine; trichlorophosphate 2 h; Heating / reflux;
参考文献
Verheijen, Jeroen C.; Yu, Ker; Toral-Barza, Lourdes; Hollander, Irwin; Zask, Arie
Bioorganic and Medicinal Chemistry Letters, 2010 , vol. 20, # 1 p. 375 - 379
反应条件
1: trichlorophosphate / 10 h / Reflux 2: methanol / 1 h / 20 °C View Scheme
参考文献
Zhu, Wufu; Zhai, Xin; Fu, Qiangqiang; Guo, Fei; Bai, Mei; Wang, Jianqiang; Wang, Haiyan; Gong, Ping
Chemical and Pharmaceutical Bulletin, 2012 , vol. 60, # 8 p. 1037 - 1045
反应条件
1: bromine / acetic acid / 30 h / 110 °C 2: N,N-diethylaniline; trichlorophosphate / 5 h / 150 °C 3: sodium tetrahydroborate / ethanol; tetrahydrofuran / 1 h / 20 °C 4: chloranil / benzene / 3 h / Reflux View Scheme
参考文献
GATEKEEPER PHARMACEUTICAL, INC.; GRAY, Nathanael, S.; ZHOU, Wenjun
Patent: WO2011/79231 A1, 2011 ;
反应条件
1.1: trichlorophosphate / 10 h / Reflux
2.1: methanol / 1 h / 20 °C
3.1: lithium diisopropyl amide / hexane; tetrahydrofuran / 1 h / -78 °C
3.2: 11 h / -78 - 20 °C
4.1: titanium(IV) isopropylate; triethylamine / chloroform / Reflux
4.2: 12 h / 20 °C
View Scheme
参考文献
Zhu, Wufu; Zhai, Xin; Fu, Qiangqiang; Guo, Fei; Bai, Mei; Wang, Jianqiang; Wang, Haiyan; Gong, Ping
Chemical and Pharmaceutical Bulletin, 2012 , vol. 60, # 8 p. 1037 - 1045
反应条件
1.1: trichlorophosphate / 10 h / Reflux
2.1: methanol / 1 h / 20 °C
3.1: lithium diisopropyl amide / hexane; tetrahydrofuran / 1 h / -78 °C
3.2: 11 h / -78 - 20 °C
4.1: sodium tetrahydroborate; methanol / 1 h / 20 °C
View Scheme
参考文献
Zhu, Wufu; Zhai, Xin; Fu, Qiangqiang; Guo, Fei; Bai, Mei; Wang, Jianqiang; Wang, Haiyan; Gong, Ping
Chemical and Pharmaceutical Bulletin, 2012 , vol. 60, # 8 p. 1037 - 1045
反应条件
1.1: trichlorophosphate / 10 h / Reflux
2.1: methanol / 1 h / 20 °C
3.1: lithium diisopropyl amide / hexane; tetrahydrofuran / 1 h / -78 °C
3.2: 11 h / -78 - 20 °C
4.1: sodium tetrahydroborate; methanol / 1 h / 20 °C
5.1: triphenylphosphine; N-bromosuccinmide / dichloromethane / 3 h / 25 °C
View Scheme
参考文献
Curis, Inc.; Bao, Rudi; Lai, Chengjung; Qian, Changgeng
Patent: US2013/102595 A1, 2013 ;
