Reference of 3177-24-0, 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 3177-24-0 as follows.
To a cooled (-60 °C) solution of (lr,4r)-4-ethoxycyclohexanamine (6.82 g, 37.9 mmol) and 2,4-dichloropyrimidine-5-carbonitrile (6 g, 34.5 mmol) in THF (115 mL) was added DIEA (15.02 mL, 86 mmol) dropwise. The resulting mixture was stirred at -60 °C for 1 h and then allowed to warm to room temperature overnight. The resulting mixture was concentrated and the residue was purified by silica gel column- 125 -ATI-2514175vl chromatography (14 percent ethyl acetate in petroleum ether). The product fractions were combined and concentrated to afford 2-chloro-4-((lr,4r)-4-ethoxycyclohexylamino)- pyrimidine-5-carbonitrile (3.33 g, 11.86 mmol, 34.4 percent yield) and 4-chloro-2-((lr,4r)-4- ethoxycyclohexylamino)pyrimidine-5-carbonitrile (5.5 g, 19.59 mmol, 56.8 percent yield;1H NMR (400 MHz, DMSO-d6) delta ppm 8.62 – 8.87 (m, 2 H), 3.61 – 3.86 (m, 1 H), 3.44 (dd, J=7.03, 2.34 Hz, 2 H), 3.12 – 3.26 (m, 1 H), 1.75 – 2.15 (m, 4 H), 1.13 – 1.44 (m, 4 H), 1.08 (td, J=6.93, 1.76 Hz, 3 H); MS (ESI) m/z 281.1 [M+l]+) as white solids. Theregiochemistry of the major isomer was confirmed by comparison with the proton spectra of 4-chloro-2-((lr,4r)-4-methoxycyclohexylamino)pyrimidine-5-carbonitrile (synthesis described herein).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3177-24-0, its application will become more common.
Reference:
Patent; SIGNAL PHARMACEUTICALS, LLC; BENNETT, Brydon, L.; ELSNER, Jan; ERDMAN, Paul; HILGRAF, Robert; LEBRUN, Laurie, Ann; MCCARRICK, Meg; MOGHADDAM, Mehran, F.; NAGY, Mark, A.; NORRIS, Stephen; PAISNER, David, A.; SLOSS, Marianne; ROMANOW, William, J.; SATOH, Yoshitaka; TIKHE, Jayashree; YOON, Won, Hyung; DELGADO, Mercedes; WO2012/145569; (2012); A1;,
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