6-(2-Fluoropyridin-3-Yl)-9-(Tetrahydro-2H-Pyran-2-Yl)-9H-Purine synthesis
- Product Name:6-(2-Fluoropyridin-3-Yl)-9-(Tetrahydro-2H-Pyran-2-Yl)-9H-Purine
- CAS Number:1093101-52-0
- Molecular formula:C15H14FN5O
- Molecular Weight:299.3
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Yield: 74%
Reaction Conditions:
with (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride;caesium carbonate in 1,4-dioxane;water at 100; for 3 h;Inert atmosphere;
Steps:
1.9
Step 9 : 6-(2-fluoropyridin-3-yl)-9-(tetrahydro-2H-pyran-2-yl)-9H-purine To a solution of 6-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purine (7.16 g, 30 mmol) in dioxane/H20 (100 mL, 10/1) was added2-fluoro-3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)pyridine (6.76 g, 30 mmol) and pumped N2 for 30 min, then PdCl2(dppf) (3%) and Cs2C03 (24.44 g, 75 mmol) were added and the resulting reaction mixture was stirred at 100°C for 3 hrs under N2 atmosphere. The mixture was diluted with water and extracted with EtOAc, washed with brine, dried over Na2S04, filtered and concentrated in vacuo. The residue was purified with column chromatography (petrol ether: EtOAc = 2: 1 to 1 : 1) to afford the desired product (6.6 g, 74%).1H NMR (CDC13): ? 9.10 (1H, s), 8.55-8.50 (1H, m), 8.40-8.37 (2H, m), 7.42-7.39 (1H, m), 5.89-5.85 (1H, m), 4.23-4.19 (1H, m) 3.86-3.79 (1H, m), 2.23-2.04 (3H, m), 1.89-1.73 (3H, m).
References:
CENTAURUS BIOPHARMA CO., LTD.;XIAO, Dengming;LI, Jijun;ZHU, Yan;HU, Yuandong;WANG, Huting;WANG, Zhe;WANG, Zanping;WEI, Yongheng;SUN, Yinghui;WU, Qiong;ZHANG, Hui;PENG, Yong;KONG, Fansheng;SUN, Ying;LUO, Hong;HAN, Yongxin WO2013/71865, 2013, A1 Location in patent:Page/Page column 27; 28
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