Pyrimidines

Electric Literature of 633328-95-7, 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. 633328-95-7, name is 5-Bromo-2-chloro-4-methylpyrimidine, molecular formula is C5H4BrClN2, 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.

Sodium hydride (550 mg, 60% purity, 13.75 mmol) was added batchwise into a solution of 2-propanol (1.75 g, 29.12 mmol) in tetrahydrofuran (50 mL) at 0 C. The resulting solution was stirred for 30 minutes at room temperature. 5-Bromo-2-chloro-4-methylpyrimidine (1.0 g, 4.82 mmol) was added at 0 C. The resulting solution was stirred for 16 hours at room temperature. The mixture was diluted with brine. The resulting solution was extracted with ethyl acetate, dried with anhydrous sodium sulfate. After filtration, the filtrate was concentrated under vacuum. The residue was purified by flash chromatography on silica gel eluting with petroleum ether/dichloromethane (2/1) to afford 5-bromo-2-isopropoxy-4-methyl-pyrimidine (350 mg, 1.51 mmol) as light yellow oil. LCMS (ESI) [M+H]+=231

According to the analysis of related databases, 633328-95-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Genentech, Inc.; Chan, Bryan; Drobnick, Joy; Gazzard, Lewis; Heffron, Timothy; Liang, Jun; Malhotra, Sushant; Mendonca, Rohan; Rajapaksa, Naomi; Stivala, Craig; Tellis, John; Wang, Weiru; Wei, BinQing; Zhou, Aihe; Cartwright, Matthew W.; Lainchbury, Michael; Gancia, Emanuela; Seward, Eileen; Madin, Andrew; Favor, David; Fong, Kin Chiu; Hu, Yonghan; Good, Andrew; US2018/282282; (2018); 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. 7752-82-1, name is 5-Bromopyrimidin-2-amine. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C4H4BrN3

To a solution of 45 (5.0 g, 28.7 mmol) in THF (50 mL) are added di-tert-butyi dicarbonate (13.8 g, 63.2 rnrnoi), TEA (12.0 rnL, 86 mmol), and DMAP (360mg, 2.87 mmol). After stirring at 60 C for 16 hour, the mixture is concentrated and purified by silica gel column chromatography (EA:PE = 1:5) to give 46 as a while solid (9.0 g, 84% yield). (MS: [M+HI 374.1)

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, 7752-82-1, 5-Bromopyrimidin-2-amine.

Reference:
Patent; IMMUNE SENSOR, LLC; THE BOARD OF REGENTS OF THE UNIVERSITY OF TEXAS SYSTEM; ZHONG, Boyu; SUN, Lijun; SHI, Heping; LI, Jing; CHEN, Chuo; CHEN, Zhijian; (270 pag.)WO2017/176812; (2017); A1;,
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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.3073-77-6, name is 2-Amino-5-nitropyrimidine, molecular formula is C4H4N4O2, molecular weight is 140.1, as common compound, the synthetic route is as follows.Product Details of 3073-77-6

EXAMPLE 92. Synthesis of 4-f5-Nitro-Pyrimidin-2-ylaininoVN-(2-PyrroIidin-l-yl- ethvD-Benzenesulfonamide (Intermediate 44)44[02871 A mixture of 2-amino-5-nitropyrimdin (7.14 mmol, 1.0 equiv), intermediate 43 (Example 91) (10.71 mmol, 1.5 equiv), Pd(OAc)2 (0.357 mmol, 0.05 equiv), Xantphos (0.714 mmol, 0.1 equiv) and potassium-tert-butoxide (14.28 mmol, 2.0 equiv) was suspended in 40 mL of dioxane and refluxed at 1000C under an argon atmosphere for 18 h. The mixture was allowed to cool to room temperature, filtered and washed with DCM. The filtrate was concentrated and the crude product precipitated out using EtOAc/Hexanes (1:5 v/v) to afford the title compound as a yellow solid (1.67g, 60%). MS (ES+): m/z = 393 (M-J-H)+. LC retention time: 1.79 min.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,3073-77-6, 2-Amino-5-nitropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; TARGEGEN, INC.; WO2008/8234; (2008); A1;,
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Pyrimidine – Wikipedia

Related Products of 4489-34-3, 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 4489-34-3, name is 4,6-Dichloro-2-methylsulfonylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

A suspension of compound A (1Og, 44.04 mmol) and cyclopropane carboxylic acid (4-mercapto~phenyl)-amide (B, 8.51 g, 44.04 mmol) in t-butanol (300 ml) was degassed by evacuation, then flushing with nitrogen. The mixture was stirred at 90 C under nitrogen atmosphere for 1 hour then the solvent was removed in vacuo. The residue was dissolved in ethyl acetate (600 ml) and washed with an aqueous solution of potassium carbonate and sodium chloride. The organic extract was dried over magnesium sulphate, concentrated to a low volume and allowed to crystallize. The product C was collected as colourless crystals, (11.15 g, 74%). 1H-NMR DMSO-d6, delta 0.82-0.89 (4H, m), 1.80-1.88 (IH, m), 7.55 (2H, d), 7.70-7.76 (3H, m), 10.49 (IH, s); M+H, 340.

According to the analysis of related databases, 4489-34-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK & CO., INC.; BANYU PHARMACEUTICAL CO., LTD.; VERTEX PHARMACEUTICALS INCORPORATED; BUSER-DOEPNER, Carolyn, A.; WO2007/136615; (2007); A2;,
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Related Products of 1005-38-5, Adding some certain compound to certain chemical reactions, such as: 1005-38-5, name is 4-Amino-6-chloro-2-(methylthio)pyrimidine,molecular formula is C5H6ClN3S, 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 1005-38-5.

Example 9A; 7-Chloro-5-(methylthio)imidazo[1,2-c]pyrimidine 75 g (427 mmol) of 4-amino-6-chloro-2-(methylthio)pyrimidine are dissolved in 3000 ml of dioxane and 750 ml of water. 101.05 g (597.81 mmol) of bromoacetaldehyde dimethyl acetal are added, and the mixture is heated under reflux for 24 h. After the reaction is complete, the dioxane is removed in vacuo and the aqueous suspension is suspended in THF, filtered with suction and washed with some THF. Drying of the solid at 40 C. under high vacuum results in 56.5 g (66% of theory) of the product.MS (ES+): m/z=200 (M+H)+.1H-NMR (400 MHz, DMSO-d6): delta=8.12 (s, 1H), 7.97 (s, 1H), 7.77 (s, 1H), 2.80 (s, 3H).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 1005-38-5, 4-Amino-6-chloro-2-(methylthio)pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; US2010/113441; (2010); A1;,
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Pyrimidine – Wikipedia

Related Products of 23945-44-0, 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. 23945-44-0, name is 2,4-Dihydroxypyrimidine-5-carboxylic acid. A new synthetic method of this compound is introduced below.

Example 16 2,4-DICHLOROPYRIMIDINE-5-CARBONYL CHLORIDE The title compound was prepared as described in the literature (Smith and Christensen, J. Org. Chem. 20:829, 1955) starting from 2,4-dihydroxypyrimidine-5-carboxylic acid. The compound was obtained by distillation; b.p. 90-100 C. (1.5 mm/Hg) in a yield of 46%; 1 H-NMR (CDCl3) delta 9.29.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,23945-44-0, 2,4-Dihydroxypyrimidine-5-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; Signal Pharmaceuticals, Inc.; US5811428; (1998); A;,
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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.23906-13-0, name is 2-Hydrazinyl-4,6-dimethylpyrimidine, molecular formula is C6H10N4, molecular weight is 138.17, as common compound, the synthetic route is as follows.COA of Formula: C6H10N4

General procedure: To a solution of 0.2 g (3.6 mmol) of potassium hydroxide in 20 mL of ethanol was added successively 0.5 g (3.6 mmol) of hydrazine 5 and 3.6 mmol of an appropriate 3-aryl-1-phenyl-2-propen-1-one 4a-4d. The mixture was boiled for 2 h and cooled to room temperature. The separated precipitate was filtered off, washed with a minimal quantity of ethanol cooled to 5C, recrystallized from an appropriate solvent or mixture of solvents, and dried to a constant weight. Further physicochemical and spectral characteristics are listed for the products purified by crystallization.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,23906-13-0, 2-Hydrazinyl-4,6-dimethylpyrimidine, and friends who are interested can also refer to it.

Reference:
Article; Erkin; Yuzikhin; Krutikov; Russian Journal of Organic Chemistry; vol. 52; 8; (2016); p. 1173 – 1178; Zh. Org. Khim.; vol. 52; 8; (2016); p. 1181 – 1185;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 51940-64-8, 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 51940-64-8, name is Ethyl 2,4-Dichloro-5-pyrimidinecarboxylate. This compound has unique chemical properties. The synthetic route is as follows.

In a 20 mL vial, (R)-3-amino-10-methyl-9,10,11,12-tetrahydro-8H-[1,4]diazepino[5?,6?:4,5]thieno[3,2-f]quinolin-8-one (INT-3) (0.095 g, 0.318 mmol), ethyl 2,4-dichloropyrimidine-5-carboxylate (0.084 g, 0.382 mmol), and Huenig’s Base (0.111 ml, 0.637 mmol) were added to 5 mL of i-PrOH. The vial was sealed and the suspension warmed to 95 C. for 24 hours. Once determined to be complete, the reaction was cooled and a precipitate formed. 5 mL of ethyl ether was added, the vial was sonicated briefly, and the product was isolated by filtration to afford compound I-18 (0.112 g, 0.232 mmol, 72.8% yield). 1H NMR (400 MHz, DMSO-d6): delta 1.18 (d, J=6.7 Hz, 3H), 1.35 (t, J=7 Hz, 3H), 3.42-3.46 (m, 2H), 3.60 (m, 1H), 4.39 (q, J=7 Hz, 2H), 7.08 (br s, 1H), 7.81 (d, J=9.0 Hz, 1H), 8.06 (d, J=4 Hz, 1H), 8.10 (d, J=9.0 Hz, 1H), 8.54 (d, J=9.2 Hz, 1H), 8.93 (s, 1H), 9.27 (d, J=9.3 Hz, 1H), 10.99 (s, 1H). MS m/z (M+H): 483.29.

According to the analysis of related databases, 51940-64-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Celgene Avilomics Research, Inc.; Alexander, Matthew David; Chuaqui, Claudio; Malona, John; McDonald, Joseph John; Ni, Yike; Niu, Deqiang; Petter, Russell C.; Singh, Juswinder; (164 pag.)US2016/75720; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 1445-39-2, Adding some certain compound to certain chemical reactions, such as: 1445-39-2, name is 2-Amino-5-iodopyrimidine,molecular formula is C4H4IN3, 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 1445-39-2.

5-[(3-aminophenyl)ethynyl]pyrimidin-2-amine 2-Amino-5-iodopyrimidine (2.21 g), bis(triphenylphosphine)palladium dichloride (350 mg) and copper(I) iodide (40 mg) were stirred in DMF (100 mL)-triethylamine (20 mL) and degassed with nitrogen for 10 min. 3-Ethynyl aniline (1.29 g) was added and the mixture heated to 95 C. for 2 hours. The solvent was evaporated and the residue was purified by trituration with DCM (20 mL) to give the title compound as a brown solid (1.25 g, 60%); 1H NMR (DMSO-d6) 5.21 (bs, 2H), 6.58-6.70 (m, 3H), 7.03-7.07 (m, 3H), 8.40 (s, 2H); MS m/e MH+211.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 1445-39-2, 2-Amino-5-iodopyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; US2008/194552; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 461-98-3 ,Some common heterocyclic compound, 461-98-3, molecular formula is C6H9N3, 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.

To a microwave tube was added 4-bromo-2-(2,6-dichlorophenyl)thiazolo[5,4-c]pyridine (60 mg, 0.17 mmol), 2,6-dimethylpyrimidin-4-amine (0.027 g, 0.22 mmol), Pd2(dba)3 (0.013 g, 0.017 mmol), XantPhos ((0.017 g, 0.034 mmol) and Cs2C03 (0.111 g, 0.34 mmol) in dioxane (3.0 mL). The mixture was degassed with N2 for 10 minutes and then irradiated in a microwave reactor at 160 C for 2 hours. After cooling to room temperature the solid was removed via filtration. The filtrate was concentrated under reduced pressure and the residue was purified with reverse phase column chromatography eluting with a 0-60% gradient of CH3CN in 0.5% NH4HC03 to give the desired product as a white solid (14 mg, 21% yield). ? NMR (500 MHz, CH3OH-??: delta 8.44 (d, J = 5.5 Hz, 1H), 7.71 (d, J = 5.5 Hz, 1H), 7.56-7.51 (m, 4H), 7.31 (s, 1H), 2.44 (s, 3H), 2.35 (s, 3H). LCMS (Method A): RT = 5.75 min, m/z: 402.0 [M+H+].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,461-98-3, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BLENCH, Toby; ELLWOOD, Charles; GOODACRE, Simon; LAI, Yingjie; LIANG, Jun; MACLEOD, Calum; MAGNUSON, Steven; TSUI, Vickie; WILLIAMS, Karen; ZHANG, Birong; WO2012/35039; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia