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. 22276-95-5, name is 5-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine. A new synthetic method of this compound is introduced below., Safety of 5-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine
To a solution of 5-bromo-4-chloro-7H-pyrrolo[2,3-i Jpyrimidine (40.0 g, 173 mmol) in dry tetrahydrofuran (700 mL) at -78 C was added rc-butyl lithium (195 mL, 2.5 M solution in hexane, 487 mmol) over the period of 2 hours. The reaction mixture was stirred for another 30 minutes at -78 C, after which ethyl chloroformate (17.8 mL, 186mmol) was added over 30 minutes. The reaction mixture was stirred for 2 hours at -60 C and then the temperature was slowly increased to 30 C. The reaction mixture was allowed to stir for 12 hours at 30 C. The progress of the reaction was monitored by TLC using 25% ethyl acetate in petroleum ether using iodine and 254 nm UV light to visualize the spot. The reaction mixture was then quenched with saturated solution of ammonium chloride (200 mL) at 0 C and the reaction mixture was extracted with ethyl acetate (*3). The combined organic layers were washed with water, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford a crude reaction mixture. The residue was purified by chromatography on silica eluting with 5-100% ethyl acetate/petroleum ether to afford ethyl 4-chloro-7H-pyrrolo[2,3-i ]pyrimidine-5- carboxylate as pale yellow solid. LRMS (ESI) calc’d for C9H7C1N302 [M-H]+: 224; found 224. 1H NMR (400 MHz, DMSO-D6): delta 13.28 (s, 1H), 8.70 (s, 1H), 8.39 (s, 1H), 4.31 (q, J= 7.2, 6.8 Hz, 2H), 1.34 (t, J= 7.6, 6.8 Hz, 3H)
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Reference:
Patent; MERCK SHARP & DOHME CORP.; AHEARN, Sean, P.; CHRISTOPHER, Matthew; JUNG, Joon; PU, Qinglin; RIVKIN, Alexey; SCOTT, Mark, E.; WITTER, David, J.; WOO, Hyun Chong; CASH, Brandon; DINSMORE, Christopher; GUERIN, David; WO2013/85802; (2013); A1;,
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