Category: 1119280-66-8

Application of 1119280-66-8, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 1119280-66-8 as follows.

step 1 : To a stirred mixture of sodium hydride (12.5 g, 520 mmol, 60% in mineral oil) in anhydrous THF (300 mL) at 0 C was added dropwise 2-chloro-5H-pyrrolo[3,2-d]pyrimidine (40.0 g, 262 mmol) dissolved in anhydrous THF (200 mL). The reaction mixture was stirred at 0 C for 15 min them SEMCl (52.5 g, 315 mmol) was added dropwise. The mixture was then stirred at RT for 1 h and then diluted with EtOAc. The organic layer was washed with water and brine, dried(Na2S04), filtered and concentrated under reduced pressure. The crude product was purified by Si02 chromatography to afford 42 g (56.4%o) of 2-chloro-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[3,2-i ]pyrimidine as an orange oil. A high-pressure tube charged with 2-chloro-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[3,2- i ]pyrimidine (2.23 g, 7.90 mmol), tributyl(l-ethoxyvinyl)stannane (3.7 g, 10.27 mmol), and Pd(PPh3)2Cl2 (200 mg) in degassed DMF (20 mL) under N2 was sealed and heated at 100 C for 16 h. The reaction mixture was cooled, diluted with EtOAc, and filtered through a pad of Celite to remove Pd solid. The filtrate was washed with water and brine, dried (Na2S04), filtered, and concentrated under reduced pressure. The crude product was dissolved in anhydrous THF (0.3 M), and 2N HC1 (5.0 eq.) was added. The reaction mixture was stirred at RT under N2 for 16 h, poured into 10% aq. NaOH solution, and then extracted with EtOAc. The organic layer was washed with water and brine, dried (Na2S04), filtered, and concentrated under reduced pressure. The crude product was purified by Si02 chromatography to afford 1.5 g (66%) of l-(5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[3,2-d]pyrimidin-2-yl)ethanone as pale yellow solid. 1H NMR (400 MHz, CDCl3) delta 9.09 (s, 1H), 7.66 (d, J = 3.2 Hz, 1H), 6.89 (d, J = 4.8 Hz, 1H), 5.60 (s, 2H), 3.49 (t, J = 8.0 Hz, 2H), 2.88 (s, 3H), 0.901 (t, J = 8.0 Hz, 2H), -0.053 (s, 9H); MS(ESI) m/z: 291 [M+].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1119280-66-8, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; ALIAGAS-MARTIN, Ignacio; CRAWFORD, James John; MATHIEU, Simon; RUDOLPH, Joachim; LEE, Wendy; WO2013/92940; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 1119280-66-8, 2-Chloro-5H-pyrrolo[3,2-d]pyrimidine, 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, category: pyrimidines, blongs to pyrimidines compound. category: pyrimidines

7-Bromo-2-chloro-5H-pyrrolo[3,2-dlpyrimidine A solution of 2-chloro-5H-pyrrolo[3,2-d]pyrimidine ( 1.54 g, 10 mmol) in DMF (10 mL) was added NBS (2.00 g, 11 mmol) at room temperature. The resulting solution was stirred for 1 h and diluted with EtOAc. The resulting solution was washed with a sat. aq. solution of NaHC03, H20 and brine. The EtOAc layer was dried ( a2S04), concentrated and purified by ISCO to provide the desired product (1.75 g, 75%). 1H NMR (400 MHz, CD3OD) delta 8.53 (s, 1H), 7.60 (s, 1H); MS m/z 234.0 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1119280-66-8, 2-Chloro-5H-pyrrolo[3,2-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; THE UNIVERSITY OF NORTH CAROLINA AT CHAPEL HILL; WANG, Xiaodong; LIU, Jing; YANG, Chao; ZHANG, Weihe; FRYE, Stephen; KIREEV, Dmitri; WO2013/52417; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 1119280-66-8, 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.1119280-66-8, name is 2-Chloro-5H-pyrrolo[3,2-d]pyrimidine, molecular formula is C6H4ClN3, molecular weight is 153.5691, as common compound, the synthetic route is as follows.

1-Bromopropane (132 mg, 1.074 mmol) was added to a solution of product of Example 1001 (150 mg, 0.977 mmol) in DMF (10 mL) followed by cesium carbonate (0.477 g, 1.074 mmol), and the mixture was stirred at 25 C for 4 h. Insoluble solids were filtered off, and filtrate was concentrated. Residue was partitioned between ethyl acetate and water. Organic layer was separated, washed with brine, dried over sodium sulphate, filtered and concentrated in vacuo. The crude product was purified by flash chromatography using 5% ethyl acetate in hexane to afford title compound (0.15 g, 74.6%) as a brown color syrup. 1H NMR (300MHz, CDC13): delta 8.68 (s, 1H), 7.51 (d, J = 3.0 Hz, 1H), 6.62 (d, J = 2.7 Hz, 1H), 4.16 (t, J = 6.9 Hz, 2H), 1.91 (m, 2H), 0.94 (t, J = 7.5 Hz, 3H).

The chemical industry reduces the impact on the environment during synthesis 1119280-66-8, I believe this compound will play a more active role in future production and life.

Reference:
Patent; GLAXOSMITHKLINE LLC; QIN, Donghui; CHEUNG, Mui; JOSHI, Hemant; TANGIRALA, Raghuram; BETHI, Sridhar, Reddy; WO2012/162129; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia