Some common heterocyclic compound, 1190380-49-4, name is 1-(Tetrahydro-2H-pyran-4-yl)-1H-pyrazol-4-amine, molecular formula is C8H13N3O, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. 1190380-49-4
To a 20 mL vial containing 5-chloro-2-ethyl-N-[trans-4-(morpholin-4-yl)cyclohexyl]-[1,3]thiazolo[5,4-d]pyrimidin-7-amine (600 mg, 1.57 mmol, 1.00 equiv) and 1-(oxan-4-yl)-1H- pyrazol-4-amine (480 mg, 2.87 mmol, 1.83 equiv) in isopropanol (15 mL) was added 0.1 mL of HC1 (4m in dioxane) at room temperature. The final reaction mixture was irradiated in a microwave reactor for 3 h at 140C. After cooling, the solids were collected by filtration purified by flash column chromatography to yield 636.7 mg (79%) of 2-ethyl-5-N-[1-(oxan-4-yl)-1H- pyrazol-4-yl] -7-N-[trans-4-(morpholin-4-yl)cyclohexyl]- [1,3 ]thiazolo [5 ,4-d]pyrimidine-5 ,7-diamine as a light yellow solid. ?H-NMR (300 MHz, DMSO) 5 9.04 (s, 1H), 7.91 (s, 1H), 7.46 (s, 1H), 7.43 (br s, 1H), 4.42-4.25 (m, 1H), 4.12-3.85 (m, 3H), 3.57 (s, 4H), 3.43 (td, 2H), 2.97 (q, 2H), 2.49 (s, 4H), 2.30-2.15 (m, 1H), 2.08-1.82 (m, 8H), 1.58-1.40 (m, 2H), 1.39-1.22 (m, 5H). LCMS (ES, m/z): 513 (M+Hj.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1190380-49-4, its application will become more common.