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With N-Bromosuccinimide; In tetrahydrofuran; at 20℃;Darkness;
(1) Dissolve 200 g of 2,4-dichloro-7H-pyrrolo [2,3-d] pyrimidine in 1500 ml of tetrahydrofuran, and add 210 g of N-bromosuccinimide in batches at room temperature until N-brominated After all the succinimide is added, stir for 1-2 hours in the dark;(2) After stirring, filter, wash with water, and recrystallize ethanol to obtain pure 5-bromo-2,4-dichloro-7H-pyrrolo [2,3-d] pyrimidine, with a purity of more than 98%. 90% yield;
64%
With N-Bromosuccinimide; In dichloromethane; at 20℃; for 4h;
To a solution of compound c-1 (1 g, 5.32 mmol) in 80 mL of dichloromethane was added NBS (1.04 g, 5.85 mmol). The reaction mixture was stirred at room temperature for 4 hours. After the reaction was completed, the mixturewas concentrated under reduced pressure and purified by combiflash to give compound p-1 (900mg, yield 64%). MSm/z(ESI):266[M+H]+.
With N-Bromosuccinimide; In dichloromethane; at 20℃; for 18h;
To a suspension of 2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine (105 mg, 0.560 mmol) in CH2Cl2 (7 niL) at room temperature, NBS (109 mg, 0.610 mmol) was added. The mixture was stirred at room temperature for 18 h. CH2Cl2 was removed in vacuo. The residue was partitioned between water and EtOAc. The organic phase was separated, washed with 5% NaHCO3, dried over Na2SO4, concentrated in vacuo to give 5-bromo-2,4-dichloro-7H- pyrrolo[2,3-d]pyrimidine (142 mg).
With triethylamine; In butan-1-ol; at 70℃; for 18h;
A solution of <strong>[900789-14-2]5-bromo-2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine</strong> (142 mg, 0.530 mmol), cyclobutylamine (0.090 mL, 1.06 mmol) and TEA (0.150 mL, 1.08 mmol) in nBuOH (6 mL) was stirred at 70 C for 18 h. CH2Cl2 and H2O were added. The organic phase was separated, washed with 5% NaHCO3, then with IN HCl, dried over Na2SO4, concentrated in vacuo to give 5-bromo-2-chloro-N-cyclobutyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (154 mg).
N-butyllithium (576 mg, 9 mmol) was slowly added dropwise to the solution of compound p-1 (800 m, 3 mmol)in 110 ml of THF at -70 C. After the reaction mixture was stirred for 1 hour, iodomethane (511 mg, 3.6 mmol) was addedat -70 C and stirred at that temperature for another 1.5 hours. After the reaction was completed, the saturated ammoniumchloride solution was added to quench at -70 C. The mixture was extracted with ethyl acetate, dried and concentratedunder reduced pressure and then purified by combiflash to give 320 mg of compound p-2. MS m/z(ESI): 202[M+H]+.
With acetic acid; zinc; In ethanol; for 7h;Reflux;
(3) 200g of pure 5-bromo-2,4-dichloro-7H-pyrrolo [2,3-d] pyrimidine, 150g of zinc powder, 1000ml of acetic acid and 1000ml of ethanol are mixed, and the mixture is heated and refluxed after the mixing is completed 7h, filtered, distilled off ethanol, and sequentially dissolved in ethyl acetate, washed with saturated aqueous sodium bicarbonate solution, washed with saturated brine, dried, and evaporated to obtain 220 g of crude product; (4) The crude product obtained in step (3) was recrystallized from n-hexane to obtain pure 5-bromo-2-chloro-7H-pyrrolo [2,3-d] pyrimidine, with a purity of more than 98% and a yield of 94.5%.
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