Category: 144927-57-1

Application of 144927-57-1, Adding some certain compound to certain chemical reactions, such as: 144927-57-1, name is Ethyl 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate,molecular formula is C9H8ClN3O2, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 144927-57-1.

To a stirred solution of ethyl 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate (4.00 g,17.7 mmol) in DCM (40 mL) was added triethylamine (7.48 mL,53.3 mmol) and N,N-dimethylaminopyridine (0.210 g,1.77 mmol) at room temperature. Benzene sulfonyl chloride (4.00 g,22.9 mmol) was then added dropwise over 10 min. The resulting reaction mixture was stirred at room temperature for another 30 min. After completion of reaction,the reaction mixture was diluted with DCM (50 mL) and washed with water. The organic layer was then washed with brine and dried over anhydrous sodium sulfate. The organic layer was filtered and concentrated under vacuum to provide crude material which was then purified by Combi-flash purifier with 20% ethyl acetate in hexane as an eluent to afford ethyl 4-chloro-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate as a light yellow solid: (5.3 g,82% yield): MS (ES) m/z 366.3(M+H)+1.

According to the analysis of related databases, 144927-57-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ACLARIS THERAPEUTICS, INC.; JACOBSEN, Eric Jon; ANDERSON, David Randolph; BLINN, James Robert; HOCKERMAN, Susan Landis; HEIER, Richard; MUKHERJEE, Paramita; (196 pag.)US2020/48262; (2020); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 144927-57-1, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.144927-57-1, name is Ethyl 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate, molecular formula is C9H8ClN3O2, molecular weight is 225.6317, as common compound, the synthetic route is as follows.

Ethyl 4-chloro-7H-pyrrolo[2,3-^pyrimidine-5-carboxylate (50.0 mg, 0.222 mmol), phenyl boronic acid (32.4 mg, 0.266 mmol) and potassium carbonate (0.332 mL, 0.665 mmol) were added to tetrahydrofuran (1.5 mL) in a microwave vial. The solution was purged with nitrogen for 5 minutes and PdCl2(dppf)-CH2Cl2 (18 mg, 0.022 mmol) was then added. The reaction was sealed and heated at 125 C by microwave irradiation for 30 minutes. The reaction mixture was diluted with EtOAc and washed with saturated sodium bicarbonate, dried over sodium sulfate, filtered and concentrated under reduced pressure. Purification of desired product was carried out by reverse phase HPLC using an acetonitrile gradient in water with 0.1% TFA modifier. Pure fractions were pooled and concentrated under reduced pressure. Saturated aqueous sodium bicarbonate and EtOAc were added to the residue. The organic layer was separated and the aqueous layer was then extracted with EtOAc (x3). The combined organic layers were then washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure to afford the product as a solid. LRMS (ESI) calc’d for C15Hi4ClN302 [M+H]+: 268, found268. 1H NMR (600 MHz, DMSO-D6) delta 13.01 (s, 1H), 8.91 (s, 1H), 8.30 (s, 1H), 7.63 (m, 2H), 7.49 (m, 3H), 3.82 (q, 2H, J= 7.04 Hz), 0.78 (t, 3H, J= 7.04 Hz).

The chemical industry reduces the impact on the environment during synthesis 144927-57-1, I believe this compound will play a more active role in future production and life.

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;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 144927-57-1, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 144927-57-1, name is Ethyl 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate. This compound has unique chemical properties. The synthetic route is as follows.

To a stirred mixture of ethyl 4-chloro-7H-pyrrolo[2,3-ii|pyrimidine-5-carboxylate (4.00 g, 17.7 mmol) and SEMC1 (4.71 mL, 26.6 mmol) in DMF (90 mL) was added sodium hydride (0.851 g, 21.3 mmol) portion-wise at 0 C. The resulting yellow suspension was stirred at 0 C for one hour and then allowed to warm to room temperature over one hour. The reaction was quenched with water slowly then extracted with ethyl acetate (x3). The combined organic layers were washed with brine (150 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on silica eluting with 0-50% ethyl acetate/hexane to afford ethyl-4-chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo [2,3 –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;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 144927-57-1, Ethyl 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, Recommanded Product: Ethyl 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate, blongs to pyrimidines compound. Recommanded Product: Ethyl 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate

To ethyl 4-chloro-7H-pyrrolo[2,3-if]pyrimidine-5-carboxylate (10.0 g, 44.3 mmol), (3-nitrophenyl)boronic acid (1 1.8 g, 70.9 mmol), PdCl2(dppf)-CH2Cl2 (3.62 g, 4.43 mmol) and aqueous sodium carbonate (2 M solution, 55.4 mL, 111 mmol) in a flask was added DMF (148 mL). The mixture was degassed for 10 minutes then heated at 1 15 C for 1.5 hours. The reaction was cooled to ambient temperature, then water was added and the mixture was extracted with DCM (*3) and EtOAc (*1). The combined organics were concentrated, diluted with EtOAc (300 mL) and washed with sorbitol/Na2C03 solution to remove excess boronic acid. The aqueous layer was extracted with EtOAc (x4). The combined organics were concentrated after which EtOAc and hexanes were added with stirring. The resulting precipitate was filtered to give solid product that was further triturated with DCM and hexanes to give ethyl 4-(3-nitrophenyl)-7H-pyrrolo[2,3- < ]pyrimidine-5-carboxylate. The combined organic fractions were concentrated under reduced pressure to give a residue containing product and DMF. Addition of MeOH and water led to formation of a precipitate which was filtered to afford additional ethyl 4-(3- nitrophenyl)-7H-pyrrolo[2,3-i ]pyrimidine-5-carboxylate. LRMS (ESI) calc'd for C,5Hi3N404 [M+H]+: 313, found 313. NMR (600 MHz, DMSO-D6) delta 13.17 (s, 1H), 8.99 (s, 1H), 8.43 (s, 1H), 8.39-8.36 (m, 2H), 8.12 (d, J= 7.8 Hz, 1H), 7.79 (t, J= 7.8 Hz, 1H), 3.93 (q, J= 7.2 Hz, 2H), 0.95 (t, J= 7.2 Hz, 3H). The synthetic route of 144927-57-1 has been constantly updated, and we look forward to future research findings. 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;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia