Category: 934524-10-4

Application of 934524-10-4, 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.934524-10-4, name is 2,4-Dichloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine, molecular formula is C13H9Cl2N3O2S, molecular weight is 342.2, as common compound, the synthetic route is as follows.

To a solution of 8 (0.80 g, 4.26 mmol), 4-methylthiophene-2-boronic acid (0.60 g, 4.26 mmol) and Pd(PPh3)4 (0.49 g, 0.43 mmol) in DMF was added Na2CO3 (2.0 M, 3.6 mL). The reaction mixture was heated 1 h at 120 0C and then cooled to room temperature. The resulting mixture was filtered through a pad of silica gel. The filtrate was concentrated and purified by silica gel chromatography (hexanes/EtOAc 100:0 to 70:30 gradient) to afford the title compound as a yellow solid (0.58 g, 55%). [0138] 1H NMR (500 MHz, DMSO-d6): delta 2.29 (s, 3H), 2.37 (s, 3H), 7.42 (d, J = 4.1 Hz, IH), 7.49 (d, J = 8.3 Hz, 2H), 7.55 (s, IH), 8.03 (d, J= 8.4 Hz, 2H), 8.07 (s, IH), 8.09 (d, J — 4.1 Hz, 2H) MS (ES+): m/z 404 (M+H)+

The chemical industry reduces the impact on the environment during synthesis 934524-10-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; TARGEGEN INC.; WO2009/49028; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 934524-10-4, 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 934524-10-4 as follows.

Example 20 N4-(benzo[d]thiazol-6-yl)-N2-(1H-indazol-6-yl)-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine To a solution of 2,4-dichloro-7-tosyl-pyrrolo[2,3-d]pyrimidine (0.1 g, 0.28 mmol) in n-butyl alcohol (0.8 mL) was added 6-aminobenzothiazole (0.046 g, 0.31 mmol) and DIPEA (0.1 mL, 0.56 mmol) at room temperature. After heating at 90 C. for 3 h, the mixture was diluted with H2O, and the precipitates were collected by filtration to give N-(2-chloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)benzolthiazol-5-amine (0.19 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,934524-10-4, its application will become more common.

Reference:
Patent; PORTOLA PHARMACEUTICALS, INC.; US2009/54425; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 934524-10-4, 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 934524-10-4 as follows.

To a solution of 3-propylthiophene (1.3 g, 10 mmol) in anhydroud THF (25 rnL) cooled at -78 0C under argon atmosphere was added ra-BuLi (2.5 M in hexanes; 4.4 mL, 11 mmol). The mixture was stirred at the same temperature for 15 min and trimethyllborate added (2.2 mL, 20 mmol). The resulting mixture was stirred at at -78 0C for 15 min and then stirred at RT for 2 h. The reaction was quenched with IM HCl (3 mL) and concentrated. The residue was taken up in water (40 mL) and extracted with EtOAc (2 x 40 mL). The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated and the crude product purified by silica gel column (CHCl3 to 10% CH3OH/CHCI3) to afford 4-propylthiophen-2-yl-2-boronic acid as an off-white solid (0.5 g, 29%). A mixture of 8 (0.28 g, 0.82 mmol), 4-propylthiophen-2-yl-2-boronic acid (0.17 g, 1.0 mmol), Pd(PPh3)4 (96 mg, 0.08 mmol) and Na2CO3 (0.32 g, 3 mmol) in anhydrous DMF (10 mL) was degassed with argon for 2 min and then heated at 120 0C in a sealed tube for 2 h. After cooling to room temperature, the solvent was removed by rotovap. The crude product was then purified by silica gel column with 1 : 1 hexanes/CHCl3 as an eluent to yield a yellow solid (90 mg, 25%).[0346] 1H NMR (500 MHz, CDCl3): delta 0.96 (t, J = 7.4 Hz, 3H), 1.60-1.75 (m, 2H), 2.42 (s, 3H), 2.63 (t, J = 1.6 Hz, 2H), 6.95 (d, J = 4.0 Hz, IH), 7.22 (s, IH), 7.74 (d, J = 4.2 Hz, IH), 7.79 (s, IH), 8.13 (d, J = 8.4 Hz, 2H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,934524-10-4, its application will become more common.

Reference:
Patent; TARGEGEN INC.; WO2009/49028; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 934524-10-4, name is 2,4-Dichloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine. A new synthetic method of this compound is introduced below., 934524-10-4

To a solution of the 2,4-dichloro-N-tosylpyrrolopyrimidine 3 (1.00 g, 2.92 mmol) in 1,4-dioxane (40 mL) and H2O (10 mL) was added phenylboronic acid (430 mg, 3.50 mmol) and Na2CO3 (620 mg, 5.84 mmol), and the mixture was degassed under argon. To this mixture was added Pd(PPh3)4 (100 mg, 6 mol %) and the reaction mixture was heated at reflux for 1 h, then cooled to room temperature and the solvent was removed in vacuo. The residue was dissolved in EtOAc (50 mL) and washed with H2O (2 * 30 mL), brine (2 * 30 mL), dried, filtered and the solvent was removed in vacuo to give a yellow residue. The residue was purified by flash chromatography (10% EtOAc/Hexanes) and recrystallised from EtOH to give 5d (600 mg, 55%) as a white solid; mp 151-155 C; deltaH (CDCl3): 8.14 (2H, d, J 8.0 Hz), 7.97 (2H, dd, J 6.0, 2.0 Hz), 7.75 (1H, d, J 4.0 Hz), 7.52-7.51 (3H, m), 7.34 (2H, d, J 8.0 Hz), 6.87 (1H, d, J 4.0 Hz), 2.41 (3H, s); deltaC (CDCl3): 160.6, 155.3, 152.9, 146.3, 136.0, 134.2, 131.1, 129.9, 129.0, 128.8, 127.1, 116.3, 104.1, 21.7; m/z (ESI): 384.0 (M[35Cl]H+), 386.0 (M[37Cl]H+); HRMS (ESI): M[35Cl]H+, found 384.0567. C19H15ClN3O2S+ requires 384.0569.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,934524-10-4, 2,4-Dichloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Article; O’Brien, Nathan J.; Brzozowski, Martin; Buskes, Melissa J.; Deady, Leslie W.; Abbott, Belinda M.; Bioorganic and Medicinal Chemistry; vol. 22; 15; (2014); p. 3879 – 3886;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia