2-氨基-5-溴-4,6-二甲基吡啶合成路线 （共 20 条）
反应条件
1: concentrated H2SO4; concentrated aqueous HNO3 2: SnCl2; aqueous HCl 3: aqueous H2SO4; KNO2 4: palladium/charcoal; platinum; aq. NaOH solution / Hydrogenation View Scheme
参考文献
Graboyes; Day
Journal of the American Chemical Society, 1957 , vol. 79, p. 6421,6423,6424
反应条件
1.1: sodium nitrite; hypophosphorous acid / H2O / 12 h / 20 °C
1.2: 87 percent / water / 6 h / 5 °C / pH 6 - 7
2.1: 90 percent / silver carbonate / CH2Cl2 / 24 h
View Scheme
参考文献
EISAI RandD MANAGEMENT CO., LTD.; Norimine, Yoshihiko; Takeda, Kunitoshi; Hagiwara, Koji; Suzuki, Yuichi; Ishihara, Yuki; Sato, Nobuaki
Patent: US2013/143907 A1, 2013 ;
反应条件
sulfuric acid; nitric acid
T=-10 - 20°C; 0.5 h;
参考文献
Heitsch, Holger; Becker, Reinhard H.A.; Kleemann, Heinz-Werner; Wagner, Adalbert
Bioorganic and Medicinal Chemistry, 1997 , vol. 5, # 4 p. 673 - 678
反应条件
1: With hydrogenchloride; pyridine hydrochloride; copper(l) chloride; sodium nitrite in dichloromethane; water
T=20°C; Sandmeyer reaction; 1.5 h; Inert atmosphere;
2: With sodium hydrogencarbonate in dichloromethane; water
T=20°C; 0.25 h; Inert atmosphere;
参考文献
Crawford, Jason B.; Chen, Gang; Carpenter, Bryon; Wilson, Trevor; Ji, Jenny; Skerlj, Renato T.; Bridger, Gary J.
Organic Process Research and Development, 2012 , vol. 16, # 1 p. 109 - 116
反应条件
1: concentrated H2SO4; concentrated aqueous HNO3
2: SnCl2; aqueous HCl
View Scheme
参考文献
Graboyes; Day
Journal of the American Chemical Society, 1957 , vol. 79, p. 6421,6423,6424
反应条件
1.1: sodium nitrite; hypophosphorous acid / H2O / 12 h / 20 °C
1.2: 87 percent / water / 6 h / 5 °C / pH 6 - 7
2.1: 90 percent / silver carbonate / CH2Cl2 / 24 h
3.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C
3.2: 89 percent / tetrahydrofuran; hexane / 0.5 h / -78 °C
4.1: m-CPBA; p-toluenesulfonic acid / CHCl3 / 24 h / 20 °C
5.1: 0.15 g / KOH / methanol / 2 h / Heating
View Scheme
参考文献
Wijtmans, Maikel; Pratt, Derek A.; Brinkhorst, Johan; Serwa, Remigiusz; Valgimigli, Luca; Pedulli, Gian Franco; Porter, Ned A.
Journal of Organic Chemistry, 2004 , vol. 69, # 26 p. 9215 - 9223
反应条件
sodium hydride in N,N-dimethyl-formamide; mineral oil
T=20°C; Inert atmosphere;
参考文献
ARIZONA BOARD OF REGENTS; HECHT, Sidney; ARMSTRONG, Jeffrey; KHDOUR, Omar; LU, Jun; ARCE, Pablo
Patent: WO2011/103536 A1, 2011 ;
Location in patent: Page/Page column 48 ;
WO 2011/103536 A1
反应条件
formic acid in water
Eschweiler-Clark methylation; Heating;
参考文献
Wijtmans, Maikel; Pratt, Derek A.; Brinkhorst, Johan; Serwa, Remigiusz; Valgimigli, Luca; Pedulli, Gian Franco; Porter, Ned A.
Journal of Organic Chemistry, 2004 , vol. 69, # 26 p. 9215 - 9223
反应条件
1.1: hydrogenchloride; pyridine hydrochloride; copper(l) chloride; sodium nitrite / dichloromethane; water / 1.5 h / 20 °C / Inert atmosphere
1.2: 0.25 h / 20 °C / Inert atmosphere
2.1: isopropylmagnesium chloride; lithium chloride / tetrahydrofuran / 2.5 h / 20 °C / Inert atmosphere
2.2: 0.67 h / Inert atmosphere; Cooling with ice
2.3: 30 °C / Inert atmosphere
View Scheme
参考文献
Crawford, Jason B.; Chen, Gang; Carpenter, Bryon; Wilson, Trevor; Ji, Jenny; Skerlj, Renato T.; Bridger, Gary J.
Organic Process Research and Development, 2012 , vol. 16, # 1 p. 109 - 116
反应条件
1: 64 percent / potassium nitrate; concd. sulfuric acid / 1 h / 20 °C
2: 98 percent / hydrogen; ammonium hydroxide / palladium on carbon / methanol / 18 h / 50 °C / 2585.74 Torr
3: 49 percent / potassium carbonate / acetone / 18 h / 20 °C
4: lithium aluminum hydride / tetrahydrofuran / 1 h / Heating
5: 75 mg / methanol / 6 h / 120 °C
View Scheme
参考文献
Tanga; Bradford; Bupp; Kozocas
Journal of Heterocyclic Chemistry, 2003 , vol. 40, # 4 p. 569 - 573
