Day: June 17, 2021

Adding a certain compound to certain chemical reactions, such as: 1979-96-0, 4,6-Dichloro-2-(methylthio)-5-nitropyrimidine, 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, Safety of 4,6-Dichloro-2-(methylthio)-5-nitropyrimidine, blongs to pyrimidines compound. Safety of 4,6-Dichloro-2-(methylthio)-5-nitropyrimidine

To a solution of compound 801 (2.46 g, 10.2 mmol) in THF (34 mL) at -20 C. was added Et3N (3.14 mL, 22.5 mmol) followed by a solution of NH3 (2.0 M in MeOH, 5.4 mL, 11 mmol). The mixture was stirred while warming to 0 C. for 1.5 h (LC/MS indicated consumption of starting materials). The reaction mixture containing compound 802 was taken forward without work-up.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1979-96-0, 4,6-Dichloro-2-(methylthio)-5-nitropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; GILEAD SCIENCES, INC.; Delaney, William E.; Link, John O.; Mo, Hongmei; Oldach, David W.; Ray, Adrian S.; Watkins, William J.; Yang, Cheng Yong; Zhong, Weidong; US2013/273005; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 22536-63-6 , The common heterocyclic compound, 22536-63-6, name is 2-Chloro-4-methoxypyrimidine, molecular formula is C5H5ClN2O, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

2.6 g of 6 (0.018 mol, 1 equiv), 1.3 g of compound 4(0.009 mmol, 0.5 equiv), 1.5 ml of 37% concd HCl (0.018 mol,1 equiv) were added in 10%, aqueous ethanol solution (25 ml)and heated at 80 C for 12 h. After that, the reaction mixturewas cooled to room temperature. The resulting precipitate wasfiltered, washed with mixture of water and ethanol, dried in vacuoat 40 C, and the obtained solid was purified by recrystallizationwith a mixture of water/ethanol to afford 2.3 g productas a white solid with the yield of 49%. Mp: 182-184 C, 1HNMR (400 MHz, DMSO-d6) d ppm: 3.93 (s, 3H, -OCH3), 6.29 (d,1H, J = 5.6 Hz, Pyrm-H), 7.14-7.19 (m, 2H, Ph-H), 7.60 (d, 1H,J = 1.2 Hz, Ph-H); 8.20 (d, 1H, J = 5.6 Hz, Pyrm-H), 9.55 (s, 1H,OH), 10.00 (s, 1H, NH); 13C NMR (100 MHz, DMSO-d6) d ppm:53.99 (-OCH3), 99.10, 107.53, 111.46, 112.37, 129.67, 140.74,153.22, 158.73, 160.04, 169.92; ESI-MS: 252.3 [M+H]+, 254.1[M+3]+, 274.6 [M+Na]+. C11H10ClN3O2 [251.67].

The synthetic route of 22536-63-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Rai, Diwakar; Chen, Wenmin; Tian, Ye; Chen, Xuwang; Zhan, Peng; De Clercq, Erik; Pannecouque, Christophe; Balzarini, Jan; Liu, Xinyong; Bioorganic and Medicinal Chemistry; vol. 21; 23; (2013); p. 7398 – 7405;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 1722-12-9, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 1722-12-9, name is 2-Chloropyrimidine, molecular formula is C4H3ClN2, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

An oven-dried round bottom flask (10 ml) was charged with 0.1ml dimethylformamide solution of complex IV (0.1 mol % for aryl bromides and 0.2 mol % for aryl chlorides), aryl boronic acid (1.2 mmol), aryl halide (1.0 mmol), K2CO3 (1.5 mmol), TBAB (1.0 mmol) and 2 ml water. The reaction mixture was then heated (to 70 C for aryl bromides and 90 C for aryl chlorides) with stirring under aerobic conditions for the required time. At the end of the reaction, the reaction mixture was cooled to room temperature and extracted with ethyl acetate (2×5 ml). The combined extract was washed with water (2×10 ml), dried over anhydrous sodium sulfate and then subjected to GC-MS analysis for identification and yield determination (from the areas under the peaks) of the products. In the case of reactions with 2-naphthylboronic acid, the combined extract was evaporated to dryness under reduced pressure and the residue was purified by column chromatography (silica gel, ethyl acetate/n-hexane) to afford the coupling products. The products were identified by 1H and 13C NMR and HR-MS analysis.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 1722-12-9, 2-Chloropyrimidine.

Reference:
Article; Babu, G. Narendra; Pal, Samudranil; Tetrahedron Letters; vol. 58; 10; (2017); p. 1000 – 1005;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 113583-35-0, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 113583-35-0, name is 2-Methanesulfonyl-4,6-dimethoxypyrimidine, molecular formula is C7H10N2O4S, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

EXAMPLE 3 (Process A) Preparation of ethyl 4-(4,6-dimethoxypyrimidin-2-yloxy)-2-methylthiomethylthiophene-3-carboxylate (Compound No. 170) 50 ml of N,N-dimethylformamide was added to 3.5 g (15.1 mmol) of ethyl 4-hydroxy-2-methylthiomethylthiophene-3-carboxylate, 3.3 g (15.1 mmol) of 4,6-dimethoxy-2-methylsulfonylpyrimidine and 2.1 g (15.2 mmol) of potassium carbonate, and the mixture was heated and stirred at from 90 to 100 C. for 2 hours. After cooling, the reaction solution was poured into water, extracted with ethyl acetate, washed with water and a saturated sodium chloride aqueous solution, and then dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure, and the residue was purified by column chromatography to obtain 2.8 g (yield: 50.0%) of the desired product.

According to the analysis of related databases, 113583-35-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Kumiai Chemical Industry Co., Ltd.; Ihara Chemical Industry Co., Ltd.; US5527763; (1996); A;,
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. 1059735-34-0, name is 7-Benzyl-2,4-dichloro-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine. A new synthetic method of this compound is introduced below., Product Details of 1059735-34-0

A mixture of 7-benzyl-2,4-dichloro-6,8- dihydro-5H-pyrido[3,4-d] pyrimidine (3.00 g, 10.2 mmol, 1.00 eq), l-tert-butyl-3 -methyl piperazine-l,3-dicarboxylate (2.62 g, 10.7 mmol, 1.05 eq), DIEA (3.30 g, 25.5 mmol, 4.45 mL, 2.50 eq) in DMSO (50.0 mL) was degassed and purged with nitrogen 3 times. The mixture was stirred at 100 C for 12 hours under a nitrogen atmosphere. The reaction mixture was diluted with DCM (200 mL), washed with brine (3 50 mL), dried over Na2S04, filtered and concentrated under reduced pressure to dryness. The residue was purified by column chromatography (Si02, Petroleum ether/Ethyl acetate = 10: 1 to 3 : 1) to give 1-tert-butyl 3- methyl 4-(7-benzyl-2-chloro-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-yl)piperazine-l,3- dicarboxylate (2.10 g, 3.81 mmol, 37.4 % yield, 91.0 % purity) as a yellow oil. ESI MS m/z 502.1 [M+H]+.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 1059735-34-0, 7-Benzyl-2,4-dichloro-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine.

Reference:
Patent; MIRATI THERAPEUTICS, INC.; ARRAY BIOPHARMA, INC.; FISCHER, John, P.; FELL, Jay, Bradford; BLAKE, James, F.; HINKLIN, Ronald, Jay; MEJIA, Macedonio, J.; HICKEN, Erik, James; CHICARELLI, Mark, Joseph; GAUDINO, John, J.; VIGERS, Guy, P.A.; BURGESS, Laurence, E.; MARX, Matthew, Arnold; CHRISTENSEN, James, Gail; LEE, Matthew, Randolf; SAVECHENKOV, Pavel; ZECCA, Henry, J.; (529 pag.)WO2017/201161; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 3177-20-6, Methyl 2,4-dichloropyrimidine-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: 3177-20-6, blongs to pyrimidines compound. Recommanded Product: 3177-20-6

(S)-(4-cyclopropyl-2-(8-(hydroxymethyl)-1-isopropyl-7-(methylsulfonyl)-3,4-dihydrobenzo[4,5]imidazo[1,2-a]pyrazin-2 (1H)-yl)pyrimidin-5-yl)methanol To a solution of methyl 2,4-dichloropyrimidine-5-carboxylate (852 mg, 4 mmol) and cyclopropylboronic acid (344 mg, 4 mmol) in THF (10 mL) was added K3PO4 (3.1 g, 12 mmol) followed by Pd(dppf)Cl2 (292 mg, 0.4 mmol) under N2. The mixture was refluxed for 4 h until the material was disappeared. The reaction mixture was cooled to rt. THF was removed under vacuum. Water (20 mL) was added and the mixture was extracted with EtOAc (20 mL*3). The organic layers were dried over anhydrous Na2SO4, filtered and concentrated under vacuum. The residue was purified by preparative TLC to afford methyl 2-chloro-4-cyclopropylpyrimidine-5-carboxylate (220 mg, 26percent yield) as a white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,3177-20-6, Methyl 2,4-dichloropyrimidine-5-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Vitae Pharmaceuticals, Inc.; Gregg, Richard E.; US2015/250787; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 33097-11-9, 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 33097-11-9 as follows.

To a mixture of 5-methyl-lH-pyrazol-3-amine (1.44 g, 14.84 mmol), DIEA (2.19 mL, 12.57 mmol) and KI (380 mg, 2.28 mmol) in DMF (13 mL) was added 4,6-dichloro-2-(methylthio)pyrimidine-5-carbaldehyde (2.55 g, 1 1.43 mmol). The mixture was stirred at rt for 3 h and then water was added. The suspended solid was collected by filtration and dried to afford crude 4-chloro-6-((5- methyl-lH-pyrazol-3-yl)amino)-2-(methylthio)pyrimidine-5-carbaldehyde (3.74 g, quantitative) as a light orange powder, which was used without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,33097-11-9, its application will become more common.

Reference:
Patent; AMBIT BIOSCIENCES CORPORATION; CHAO, Qi; HADD, Michael, J.; HOLLADAY, Mark, W.; ROWBOTTOM, Martin; WO2012/30924; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 5305-45-3, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 5305-45-3, name is 4,6-Dichloropyrimidine-5-carbonitrile, molecular formula is C5HCl2N3, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Intermediate 1 To a solution of 4-fluoro-2-methyl-lH-indol-5-ol (200 mg, 1.21 mmol) in a mixture of acetonitrile (4 mL) and N, N-dimethylformamide (1 mL) was added potassium carbonate (200 mg, 1.45 mmol). The reaction mixture was stirred for lh at room temperature before a suspension of 4, 6-dichloropyrimidine-5-carbonitrile (221 mg, 1.27 mmol) in 3 mL of acetonitrile was added. This mixture was stirred at room temperature for 1 h. TLC was checked and the reaction was completed. The mixture was diluted with water and ethyl acetate. The layers were separated and the aqueous phase was extracted twice with ethyl acetate. The combined organic phases were washed once with water, then with brine, dried over sodium sulfate, filtered, and the filtrate was concentrated in vacuo to give the desired product as brown solids (365 mg, 99% yield). 1H MR (400 MHz, DMSO-d6) delta 11.46 (br, 1H), 8.83 (s, 1H), 7.17 (d, J = 8.8 Hz, 1H), 7.00 (t, J = 7.6 Hz, 1H), 6.27 (s, 1H), 2.41 (s, 3H); ESI-MS: calcd for (C14H8C1FN40) 302, found 303 (MH+).

According to the analysis of related databases, 5305-45-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NANTBIOSCIENCE, INC.; TAO, Chunlin; POLAT,, Tulay; WEINGARTEN, Paul; NALLAN, Laxman; ARP, Forrest; WANG, Qinwei; HO, David; (129 pag.)WO2016/138527; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 183438-24-6, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 183438-24-6, name is 5-Bromo-2-iodopyrimidine, molecular formula is C4H2BrIN2, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

A suspension of 5-bromo-2-iodopyrimidine (2.81 g, 9.86 mmol), vinyl boronic acid pinacol ester (1.98 mL, 11.7 mmol) and cesium carbonate (6.30 g, 19.5 mmol) in dioxane (39 mL) and water (14 mL) was degassed by sparging with Ar. [1,1?-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with DCM (364 mg, 486 mumol) was added and the reaction heated to 100 C for 4 h. The reaction mixture was concentrated in vacuo to remove the dioxane, then partitioned between EtOAc and water. The aqueous layer was extracted EtOAc (×2), then the combined organic layers dried (MgSO4), filtered and concentrated in vacuo. FCC (2-16% EtOAc in toluene) provided the title compound as an oil (0.850 g). 1H NMR (CDCl3, 300 MHz): delta 8.74 (s, 2H), 6.83 (dd, J = 17.4, 10.5 Hz, 1H), 6.62 (dd, J = 17.4, 1.8 Hz, 1H), 5.76 (dd, J = 10.5, 1.8 Hz, 1H).

According to the analysis of related databases, 183438-24-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BRONNER, Sarah M.; CRAWFORD, James J.; CRIDLAND, Andrew; CYR, Patrick; FAUBER, Benjamin; GANCIA, Emanuela; GOBBI, Alberto; HURLEY, Christopher; KILLEN, Jonathan; LEE, Wendy; RENE, Olivier; VAN NIEL, Monique Bodil; WARD, Stuart; WINSHIP, Paul; ZBIEG, Jason; (439 pag.)WO2018/83105; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 2565-47-1, Adding some certain compound to certain chemical reactions, such as: 2565-47-1, name is 1-Methylpyrimidine-2,4,6(1H,3H,5H)-trione,molecular formula is C5H6N2O3, 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 2565-47-1.

(b) 6-Chloro-3-methylpyrimidine-2,4(l/J,3H)-dioneWater (2.7 mL) is added dropwise to a suspension of 1-methylpyrimidine- 2,4,6(lH,3H,5No.)-trione (14.2 g, 100 mol) in POCl3 (95 mL) at 0 0C. The reaction mixture is then heated at 80 C for 5 hours. The resulting brownish solution is cooled, and POCl3 is evaporated under reduced pressure. The residue is treated with MeOH, and the obtained solid is recrystallized from ethanol to give 11.5 g product (Yield: 71.6%). m.p. = 279-282 0C (dec) [Lit.2: 280-282 0C]. 1H NMR (400 MHz, DMSO-d6) (53.10 (S, 3H), 5.90 (S, IH), 12.4 (br, IH).

According to the analysis of related databases, 2565-47-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; INTRA-CELLULAR THERAPIES, INC.; WO2006/133261; (2006); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia