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., category: pyrimidines
Step 1 : To a stirred solution of mixture of 4-(2,4-difluorophenyl)-1-(3-fluoro-4-(4,4,5,5- tetramethyl-1 ,3,2-dioxaborolan-2-yl)phenyl)-3-methylimidazolidin-2-one (0.2 g, 0.462 mmol, 1 equiv), in 1 ,4-dioxane: water (10 mL: 3 mL) was added 5-bromo-7-methyl-7H- pyrrolo[2,3-d]pyrimidin-4-amine (0.095 g, 0.416 mmol, 0.9 equiv), potassium phosphate (0.196 g, 0.924 mmol, 2 equiv), Pd2(dba)3 (0.021 g, 0.0231 mmol, 0.05 equiv) and tri-tert- butylphosphonium tetrafluoroborate (0.0133 g, 0.0462 mmol, 0.1 equiv) under argon atmosphere, then the mixture was heated to 100C for 6h in a sealed tube. Reaction mixture was monitored by TLC and after consumption of the starting material, the reaction mixture was filtered through celite, dried over Na2S04, and concentrated to obtain the crude product. Crude product was purified by flash column chromatography on silica gel, and the compound was eluted with 2 % MeOH : DCM mobile phase. The pure fractions were evaporated to obtain 1-(4-(4-amino-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-3- fluorophenyl)-4-(2,4-difluorophenyl)-3-methylimidazolidin-2-one as off white solid (0.07 g, 34.5 %). LCMS (ES) m/z = 453.1 [M+H]+. H NMR (400 MHz, DMSO-d6) delta ppm 2.62 (s, 3H), 3.68 – 3.69 (m, 1 H), 3.71 (s, 3H), 4.28 (t, J = 9.6 Hz, 1 H), 4.97 – 5.01 (m, 1 H), 5.93 (br. S., 2H), 7.15 (t, J = 6.4 Hz, 1 H), 7.24 (s, 1 H), 7.32 (t, J = 8.8 Hz, 2H), 7.40 – 7.49 (m, 2H), 7.69 (d, J = 13.2 Hz, 1 H), 8.1 1 (s, 1 H).
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Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; AXTEN, Jeffrey Michael; FAUCHER, Nicolas Eric; DAUGAN, Alain Claude-Marie; KETHIRI, Raghava Reddy; KRISTAM, Rajendra; VENKATESHAPPA, Chandregowda; (247 pag.)WO2017/46737; (2017); A1;,
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