Electric Literature of 151049-87-5, 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 151049-87-5 as follows.
In a 2mL microwave tube, a mixture of 4-(7-morpholinoquinazolin-5- yl)oxycyclohexanamine (27 mg, 0.082 mmol), 3-bromo-1-methyl-pyrazole (9.5 muL, 0.0999 mmol), allyl(chloro)palladium (0.8 mg, 0.004 mmol), di-tert-butyl(2′,4′,6′- triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphane (4 mg, 0.008 mmol), and sodium 2-methylpropan-2-olate (83 muL of 2 M in tetrahydrofuran, 0.166 mmol) in tBuOH (400 muL) was heated to 90C and allowed to stir overnight. The reaction was diluted with DCM and filtered through celite and the filtrate was concentrated under reduced pressure. The residue was chromatographed over 12g silica gel using 0-10% MeOH/DCM as eluent to yield 1-methyl-N-((1s,4s)-4-((7-morpholinoquinazolin-5- yl)oxy)cyclohexyl)-1H-pyrazol-3-amine (12.5 mg, 36%).1H NMR (400 MHz, CDCl3) delta 9.43 (d, J = 1.5 Hz, 1H), 9.09 (d, J = 1.6 Hz, 1H), 7.10 (d, J = 2.2 Hz, 1H), 6.78 (d, J = 2.1 Hz, 1H), 6.57 (d, J = 1.9 Hz, 1H), 5.53 (t, J = 2.0 Hz, 1H), 4.76 – 4.66 (m, 1H), 3.88 (dt, J = 5.0, 3.0 Hz, 4H), 3.72 (d, J = 1.5 Hz, 3H), 3.49 – 3.33 (m, 5H), 2.18 (dd, J = 13.8, 4.1 Hz, 3H), 1.99 (dt, J = 11.7, 3.7 Hz, 2H), 1.89 – 1.63 (m, 4H). ESI-MS m/z = 409.33 (M+1)+.
According to the analysis of related databases, 151049-87-5, the application of this compound in the production field has become more and more popular.