Tag: M.W:200-300

Electric Literature of 1211443-61-6, Adding some certain compound to certain chemical reactions, such as: 1211443-61-6, name is 2-Chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide,molecular formula is C14H17ClN4O, 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 1211443-61-6.

To a suspension of 2-chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide (5) (500 mg, 1.71 mmol) in 10 mL 1,4-dioxane was added 2-Amino-5-nitropyridine (356 mg, 2.56 mmol), Pd(OAc)2 (9.6 mg, 0.043 mmol), BINAP (53 mg, 0.09 mmol) and Cs2CO3 (834 mg, 2.56 mmol) and the flask was purged with Ar. Then the flask was sealed and the mixture was heated for 12 h at 100. The reaction was cooled to room temperature, the solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 200 mg (30%) of 7 as a yellow solid. 1H NMR (400 MHz, Chloroform-d) delta 9.29 (d, J = 2.7 Hz, 1H), 8.90 (s, 1H), 8.66 (d, J = 9.3 Hz, 1H), 8.47 (dd, J = 9.4, 2.8 Hz, 1H), 7.26 (s, 1H), 6.55 (s, 1H), 4.84 (p, J = 8.9 Hz, 1H), 3.18 (s, 6H), 2.63 – 2.47 (m, 2H), 2.24 – 2.02 (m, 4H), 1.90 – 1.66 (m, 2H).

According to the analysis of related databases, 1211443-61-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Li, Yongtao; Guo, Qingxiang; Zhang, Chao; Huang, Zhi; Wang, Tianqi; Wang, Xin; Wang, Xiang; Xu, Guangwei; Liu, Yanhua; Yang, Shengyong; Fan, Yan; Xiang, Rong; Bioorganic and Medicinal Chemistry Letters; vol. 27; 15; (2017); p. 3231 – 3237;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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.6299-85-0, name is Methyl 2,6-dichloropyrimidine-4-carboxylate, molecular formula is C6H4Cl2N2O2, molecular weight is 207.0142, as common compound, the synthetic route is as follows.Recommanded Product: 6299-85-0

To a mixture of 2,6-dichloro-pyrimidine-4-carboxylic acid methyl ester [1 g, 4.83 mmol, Intermediate (54)] and N,N-diisopropylethylamine (1.27 mL, 7.25 mmol) in THF (16 rriL) is added 2- (4-methoxyphenyl)-ethylamine (707 muL, 4.83 mmol). The resulting mixture is stirred at ambient temperature for 20 hours and poured into 50 mL water and extracted three times with 40 mL ethyl acetate. The organic extracts are combined and washed with 20 mL brine, dried over magnesium sulfate, filtered and concentrated to afford a solid which is purified via flash column chromatography on silica gel (35 g) eluting with 5 to 50% EtOAc in heptane gradient to afford 2-chloro-6-[2-(4- methoxy-phenyl)-ethylamino]-pyrimidine-4-carboxylic acid methyl ester [1 g, 64.5%, Intermediate (55)]. LCMS: Rtau = 2.9 minutes, MS: 322 (M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6299-85-0, Methyl 2,6-dichloropyrimidine-4-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; SANOFI-AVENTIS U.S. LLC; HARRIS, Keith John; WO2008/39882; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 935534-47-7, 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. 935534-47-7, name is 5-Bromo-4-(trifluoromethyl)pyrimidin-2-amine. A new synthetic method of this compound is introduced below.

Synthesis of 5-(4,4,5,5-tetramethyl(l,3,2-dioxaborolan-2-yl))-4- (trifluoromethyl)pyrimidine-2-ylamine[0095] To a dry 500 mL flask was added 5-bromo-4-(trifluoromethyl)-2-pyrimidylamine (10.1 g, 41.7 mmol), potassium acetate (12.3 g, 125.2 mmol), 4,4,5,5-tetramethyl-2-(4,4,5,5- tetramethyl-l ,3,2-dioxaborolan-2-yl)-l,3,2-dioxaborolane (11.6 g, 45.9 mmol) and dioxane (150 mL). Argon was bubbled through the solution for 15 minutes, at which time l,l’-bis(diphenylphosphino)ferrocene palladium (II) chloride (1.7 g, 2.1 mmol) was added. The reaction was refiuxed in a 115 C oil bath for 6 hours under argon. After cooling to room temperature, the dioxane was removed in vacuo. EtOAc (500 mL) was added and the resulting slurry was sonicated and filtered. Additional EtOAc (500 mL) was used to wash the solid. The combined organic extracts were concentrated and the crude material was purified by Si02 chromatography (30-40% EtOAc/hexanes) yielding 4.40 g of an off white solid. By ? NMR the material was a 1 : 1 mixture of boronate ester and 2-amino-4- trifluoromethylpyrimidine byproduct. The material was used as is in subsequent Suzuki reactions. LCMS (m/z): 208 (MH+ of boronic acid, deriving from in situ product hydrolysis on LC). l NMR (CDC13): delta 8.72 (s, 1H), 5.50 (bs, 2H), 1.34 (s, 12H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,935534-47-7, its application will become more common.

Reference:
Patent; DANA-FARBER CANCER INSTITUTE, INC.; ZHAO, Jean J.; WANG, Qi; WO2012/109423; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 1211443-61-6, 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. 1211443-61-6, name is 2-Chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide, molecular formula is C14H17ClN4O, 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.

General procedure: To a suspension of 2-chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide (5) (586 mg, 2 mmol) in 20 mL 1,4-dioxane were added compound 3a-f, 3i-u(2 mmol), Pd(OAc)2 (11 mg, 0.05 mmol), BINAP (62 mg, 0.1 mmol) and Cs2CO3 (978 mg, 3 mmol) and the flask was purged with Ar. Then the flask was sealed and the mixture was heated for 12 h at 100. The reaction was cooled to rt, the solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 4a-f, 4i-o, 4r-u.

According to the analysis of related databases, 1211443-61-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Li, Yongtao; Guo, Qingxiang; Zhang, Chao; Huang, Zhi; Wang, Tianqi; Wang, Xin; Wang, Xiang; Xu, Guangwei; Liu, Yanhua; Yang, Shengyong; Fan, Yan; Xiang, Rong; Bioorganic and Medicinal Chemistry Letters; vol. 27; 15; (2017); p. 3231 – 3237;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 6299-85-0, Methyl 2,6-dichloropyrimidine-4-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: Methyl 2,6-dichloropyrimidine-4-carboxylate, blongs to pyrimidines compound. Recommanded Product: Methyl 2,6-dichloropyrimidine-4-carboxylate

Example 226 (Z)-methyl 2-(((1-(4-((2,4-dioxothiazolidin-5-ylidene)methyl)pyrimidin-2-yl)piperidin-4-yl)methyl)amino)pyrimidine-4-carboxylate was prepared as follows.Methyl 2-((piperidin-4-ylmethyl)amino)pyrimidine-4-carboxylate was prepared as follows: A 40 mL round-bottomed vial was charged with tert-butyl 4-(aminomethyl)piperidine-1-carboxylate (1.76 mmol, 1.1 equiv.), acetonitrile (4 mL), DiPEA (2.37 mmol, 1.5 equiv.), methyl 2,6-dichloropyrimidine-4-carboxylate (1.58 mmol, 1 equiv.), and then shaken at 85 C. for 72 h. The reaction mixture was concentrated under reduced pressure and purified on SiO2 using a Biotage and a 10-50% EtOAc/hexanes gradient to provide the desired protected amine (233 mg, 552 mg theoretical, 42%). Methyl 2-((piperidin-4-ylmethyl)amino)pyrimidine-4-carboxylate was prepared using the general TFA de-protection procedure and used directly in the general displacement procedure to provide the title compound (4 mg, 73.4 mg theoretical, 5%). LC-MS m/z 456.1 (M+1).

The synthetic route of 6299-85-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jasco Pharmaceuticals, LLC; US2011/152235; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 941685-26-3, name is 4-Chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine, the common compound, a new synthetic route is introduced below. Formula: C12H18ClN3OSi

Step 1: 4-chloro-6-methyl-7-{[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3d]pyrimidine To a stirred solution of Intermediate 2a (100 mg, 0.352 mmol) in THF (1 mL) was added LDA (2.0M; 0.19 mL, 0.39 mmol) dropwise at -78 C. The reaction mixture was stirred at this temperature for 40 minutes, then MeI (0.11 mL, 1.8 mmol) was added and the reaction was stirred at -78 C for an additional 40 minutes before being quenched with EtOAc and poured into a mixture of EtOAc and silica gel. The resulting mixture was concentrated in vacuo to afford a crude solid that was purified by column chromatography on silica gel, eluting with EtOAc/hexane (2-20%) to afford the desired product as a colorless oil. LRMS calc’d for C13H21ClN3OSi [M+H]+, 298; found 298. 1H NMR (500 MHz, CDCl3) delta 8.60 (s, 1H), 6.40 (s, 1H), 5.65 (s, 2H), 3.51 (t, 2H), 2.56 (s, 3H), 0.90 (t, 2H), 0.06 (s, 9H).

The synthetic route of 941685-26-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck Sharp & Dohme Corp.; GUERIN, David Joseph; BRUBAKER, Jason, D.; MARTINEZ, Michelle; JUNG, Joon, O.; ANTHONY, Neville, J.; SCOTT, Mark, E.; HOFFMAN, Dawn Marie Mampreian; WOO, Hyun Chong; DINSMORE, Christopher, J.; (75 pag.)EP2629777; (2018); B1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 1189169-37-6, 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. 1189169-37-6, name is 1-(5-Bromopyrimidin-2-yl)ethanone, molecular formula is C6H5BrN2O, 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.

5-Bromo-2-(1,1-difluoroethyl)pyrimidine 1-(5-bromopyrimidin-2-yl)ethanone (304 mg, 1.514 mmol) in anhydrous DCM (50 ml), under nitrogen, was treated w Diethylaminosulfur trifluoride (1220 mg, 1 ml, 7.57 mmol). After 12 hours of stirring additional Diethylaminosulfur trifluoride (610 mg, 0.5 ml, 3.75 mmol) was added. This was repeated again after 24 hours, Diethylaminosulfur trifluoride (610 mg, 0.5 ml, 3.75 mmol). After 36 hours the reaction was quenched with sat. NaHCO3 and extracted with AcOEt, washed with Brine and dried over Na2SO4, filtered and concentrated. The reaction was purified by column chromatography on silica gel (petroleum ether: EtOAc=1:0 to 0:1) to afford 5-bromo-2-(1,1-difluoroethyl)pyrimidine (298 mg, 88% yield). 1H NMR (CDCl3 500 MHz): delta 8.92 (s, 21-1), 2.08 (t, 2H).

According to the analysis of related databases, 1189169-37-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; H. Lundbeck A/S; Kilburn, John Paul; Rasmussen, Lars Kyhn; Jessing, Mikkel; Eldemenky, Eman Mohammed; Chen, Bin; Jiang, Yu; US2014/107335; (2014); 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. 1436686-17-7, name is Ethyl 5-bromopyrazolo[1,5-a]pyrimidine-3-carboxylate. A new synthetic method of this compound is introduced below., HPLC of Formula: C9H8BrN3O2

To a solution of cyclopropylboronic acid (174mg, 2.1mmol), KOAc (330mg, 3.4mmol), ethyl 5-bromopyrazolo[l,5-a]pyrimidine-3-carboxylate (500mg, 1.7mmol) in dioxane (15ml) was added PdCl2(dppf).DCM (138mg, 0.17mmol). The reaction mixture was stirred at 90 C for 2.5 h under a nitrogen atmosphere and then concentrated in vacuo. The residue was diluted with water and then extracted with DCM (20 x 3). The combined organic layers were washed with brine and dried over anhydrous Na2S04, filtered and concentrated in vacuo. The residue was purified by a silica gel column chromatography (DCM/EA (v/v) = 6/1) to give the title compound as a brown solid (220 mg, 57%). H NMR (300 MHz, CDC1 ): delta (ppm) 8.51 (d, J = 7.2 Hz, 1H), 8.47 (s, 1H), 6.78 (d, J = 7.2 Hz, 1H), 4.39 (q, J= 7.1 Hz, 2H), 2.25-2.16 (m, 1H), 1.41 (t, J= 7.1 Hz, 3H), 1.33-1.25 (m, 2H), 1.25- 1.14 (m, 2H).

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, 1436686-17-7, Ethyl 5-bromopyrazolo[1,5-a]pyrimidine-3-carboxylate.

Reference:
Patent; CALITOR SCIENCES, LLC; SUNSHINE LAKE PHARMA CO., LTD.; XI, Ning; LI, Minxiong; LI, Xiaobo; WO2015/73267; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 74901-69-2 , The common heterocyclic compound, 74901-69-2, name is 2,4-Dichloro-6,7-dihydrothieno[3,2-d]pyrimidine, molecular formula is C6H4Cl2N2S, 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.

12.1 (2-chloro-6,7-dihydrothieno[3,2-d]pyrimidin-4-yl)-(3-fluorophenyl)-amine (III-7) 4 g (II) are placed in 15 ml dimethylformamide, then 4.5 ml diisopropylethylamine are added followed by 2.5 ml 3-fluorophenylamine. The reaction mixture is heated to 120 C. until there is no further reaction then cooled and evaporated down. The residue is mixed with water. The product is extracted with dichloromethane and purified by chromatography (silica gel, petroleum ether/ethyl acetate 80/20 to 60/40). 2.6 g (III-7) are obtained in the form of a solid. Analytical HPLC (method A): RT=3.27 min

The synthetic route of 74901-69-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2012/35143; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 38696-20-7, name is 5-Bromo-2-phenylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows. category: pyrimidines

250ml four-necked flask, in a nitrogen-purged atmosphere,0.01 mol of 5-bromo-2-phenylpyrimidine, 0.015 mol of intermediate J1, 0.03 mol of sodium tert-butoxide, 1 x 10-4 mol of Pd2 (dba) 3,1 X 10-4 mol tri-tert-butylphosphine,150ml of toluene, heated to reflux for 24 hours, sampling point plate, the reaction was complete; natural cooling, filtration, the filtrate was swirled through a silica gel column to obtain the target product, purity 98.7percent, yield 67.1percent.

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, 38696-20-7, 5-Bromo-2-phenylpyrimidine.

Reference:
Patent; Jiangsu March Optoelectric Technology Co., Ltd.; Tang Dandan; Xu Kai; Li Chong; Zhang Xiaoqing; Zhang Zhaochao; (45 pag.)CN106397415; (2017); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia