Reference of 16357-69-0, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 16357-69-0 as follows.
General procedure: To the solution of corresponding quinazolone intermediate 13a(13b, 13c or 13d) in DCM (4 mL/1 mmol substrate)was added TFA (1mL/1 mmol substrate) dropwise at 0 C, and the resultant mixturewas stirred at room temperature. After 13a (13b, 13c or 13d) wastotally consumed, saturated NaHCO3 solution was added dropwiseat 0 C to adjust the PH value to 7. Following extraction with DCM,the organic layer was washed with brine, dried over anhydrousNa2SO4, and concentrated in vacuo to afford the Boc-deprotectedsecondary amine as slightly yellow solid.The mixture of corresponding Boc-deprotected secondaryamine (1.0 eq), 6-chloro-9H-purine (1.5 eq), DIPEA (4.0 eq) and t-BuOH (15 mL/1 mmol secondary amine) was stirred at 80 C underN2 atmosphere. After the secondary aminewas totally consumed, t-BuOH was removed in vacuo, and the residue was dissolved inDCM. The solution was washed with saturated NaHCO3 solution,dried over anhydrous Na2SO4, and concentrated in vacuo. Finally,the crude product underwent flash column chromatography (DCM/EA 5:1-1:1, V/V) to afford the purine derivative (14 or 15e17) aspale solid. Compounds with 4-aminopyrimidine-5-carbonitrile, 2-amino-6-methylpyrimidine-5-carbonitrile, 2-fluoro-9H-purine or2-chloro-9H-purine as HBs were prepared via similar procedure tothat for 14e17. However, the eluents utilized in the final flash columnchromatography of 21, 22, 24, 25 and 27 were different (DCM/EA 15:1-5:1, V/V, for 21, 24 and 27; DCM/EA 20:1-8:1, V/V, for22 and 25). The NMR spectra of 14e17, 28 and 29 indicated theexistence of rotamers.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,16357-69-0, its application will become more common.
Reference:
Article; Tao, Qiangqiang; Chen, Yuqing; Liang, Xiao; Hu, Yongzhou; Li, Jiaming; Fang, Fang; Wang, Huchuan; Meng, Chang; Liang, Jingtai; Ma, Xiaodong; Gui, Shuangying; European Journal of Medicinal Chemistry; vol. 191; (2020);,
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