Related Products of 1337532-51-0, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 1337532-51-0, name is 5-Bromo-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine. A new synthetic method of this compound is introduced below.
To a mixture of 1-(4-bromo-3-methylphenyl)-3-(3,5-difluorophenyl)pyrrolidin-2-one (0.6 g, 1.6 mmol, 1.0 equiv), bis(pinacolato)diboron (0.41 g, 1.6 mmol, 1.0 equiv), and potassium carbonate (0.48 g, 4.9 mmol, 3.0 equiv) was added 1 ,4-dioxane (10 ml_), and the mixture was degassed with Ar gas for 10 minutes. PdCI2 (dppf)-CH2Cl2 adduct (0.1 1 g, 0.08 mmol, 0.05 equiv) was added and degassed with Ar for 10 minutes. The reaction mixture was stirred for 3 h at 100 C in a sealed vessel. After consumption of SM, the reaction mixture was cooled to room temperature. 5-bromo-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (0.37 g, 1.6 mmol, 1.0 equiv) and saturated aqueous NaHC03 (12 ml_) were added and degassed with argon for 10 min. PdCl2(dppf)-CH2Cl2 adduct (0.1 1 g, 0.08 mmol, 0.05 equiv) was added, the vessel was sealed, and the reaction mixture was stirred overnight at 100C. After consumption of SM, the reaction mixture was poured onto water and extracted with ethyl acetate (2 x 30 ml_). The combined organic layers were washed with brine solution (30 ml_), dried over Na2S04 and evaporated the solvent under reduced pressure to afford the crude product. The crude product was purified by flash column chromatography with 100 – 200 silica gel (24g column) and eluted with 3% MeOH in DCM mobile phase to afford the titled product 1-(4-(4-amino-7-methyl-7/-/-pyrrolo[2,3- d]pyrimidin-5-yl)-3-methylphenyl)-3-(3,5-difluorophenyl)pyrrolidin-2-one (0.1 g, 14%) as off white solid. LCMS (ES) m/z = 434.2 [M+H]+. H NMR (400 MHz, DMSO-d6) delta 2.21 – 2.27 (m, 4H), 2.54 – 2.61 (m, 1 H), 3.73 (s, 3 H), 3.93 – 4.07 (m, 3H), 5.54 (br, 2 H), 7.10 – 7.15 (m, 4 H), 7.25 (d, J=8.0 Hz, 1 H), 7.60 – 7.68 (m, 2 H), 8.13 (s, 1 H).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1337532-51-0, its application will become more common.
Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; AXTEN, Jeffrey M.; MEDINA, Jesus Raul; WO2015/136463; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia