Pyrimidines

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.4212-49-1, name is 5-Ethyluracil, molecular formula is C6H8N2O2, molecular weight is 140.14, as common compound, the synthetic route is as follows.4212-49-1

Step A: Synthesis of 2,4-dichloro-5-ethylpyrimidine. To a suspension of 5-ethyluracil (1 g, 7.1 mmol) in POCl3 (4.5 mL) was slowly added N,N-dimethylaniline (1 mL). The reaction was heated at reflux (~120 C) for 5 h until the starting material was completely dissolved and the entire solution turned a purple color. The mixture was allowed to cool and poured very slowly into ice (~40 g). The resulting ppt was filtered and washed with ice water. The ppt was dissolved with a minimal amount of DCM and poured onto a short column of silica gel, and the product (1.2 g, ~ 100 %) was obtained by column chromatography with DCM. 1H NMR (400 MHz, CDCl3) delta 8.42 (s, 1 H), 2.75 (q, 2 H, J = 7.6 Hz), 1.29 (t, 3 H, J = 7.6 Hz).

Statistics shows that 4212-49-1 is playing an increasingly important role. we look forward to future research findings about 5-Ethyluracil.

Reference:
Patent; Taisho Pharmaceutical Co. Ltd.; Arena Pharmaceuticals, Inc.; EP1464335; (2004); A2;,
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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.

Example 1; Pd(PPh3VNaHCO3DME/H,O/reflux [00203] 2,2-Dimethyl-N-(2-pyrimidin-2-yI-phenyI)-propionamide: A 5 L flask was charged with the above depicted boronic acid as a tetrahydrate (281.4 grams, 960 mmoles), 2- chloropyrimidine (100 g, 874 mmoles), NaHCO3 (146.8 grams, 1.746 moles), and Pd(PPh3)4 (10.0 grams, 8.72 mmoles). Water (IL) and dimethoxyethane (IL) were added, and the mixture was heated slowly to 83 0C (internal temperature) over a 1 hour period with overhead stirring. After ~2 hours all solids had dissolved. The reaction was allowed to stir for 8 hours. The mixture was cooled to room temperature and stirred overnight after which time a thick precipitate had formed. The crude mixture was diluted with water (2L) and stirred for an additional 2 hours after which time the mixture was filtered and the solids were washed sequentially with water, 0.1 N NaOH, and water again. The solids were then dried under high vacuum at 50 0C to afford the title compound (-233 grams) as a tan powder.

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. 1722-12-9, 2-Chloropyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2007/56330; (2007); A1;,
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Pyrimidine – Wikipedia

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 145783-14-8, name is 4,6-Dichloro-5-nitro-2-(propylthio)pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. 145783-14-8

Example 3. Preparation of l-^SaR^S^R^aSV-ftS-Amino–chloro-l- phiropylthioJpyrimidin-^yllaminoJ-ljl-dimethyltetrahydro-SaH- cyclopenta[ 99%). The catalyst was filtered off and washed with methyl-tert-butylether (117 kg). The hydrogenation was repeated with a second portion of 4,6-Dichloro-5-nitro-2-(propylthio)pyrimidine (71 kg). The two hydrogenation solutions were combined. Water was separated off and the organic layer was distilled under reduced pressure and at a jacket temperature of 300C. To the resulting brown oil ethylene glycol (221 kg) was charged and the distillation was continued until no more methyl-tert-butylether was distilling off.

Statistics shows that 145783-14-8 is playing an increasingly important role. we look forward to future research findings about 4,6-Dichloro-5-nitro-2-(propylthio)pyrimidine.

Reference:
Patent; ASTRAZENECA AB; AUFDENBLATTEN, Rhony; BOHLIN, Martin, Hans; HELLSTROeM, Helena; JOHANSSON, Peter, W; LARSSON, Ulf, G; RECKNAGEL, Mikaela; WEISS, Ursula, heiress of WEISS Andreas (Deceased); WO2010/30224; (2010); A1;,
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Pyrimidine – Wikipedia

156-81-0, 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. 156-81-0, name is Pyrimidine-2,4-diamine, the common compound, a new synthetic route is introduced below.

A solution of 2-bromo-1-(5-chloro-2,4-dimethoxyphenyl)ethanone 3 (140 mg, 0.47 mmol) and pyrimidine-2,4-diamine (50 mg, 0.45 mmol) in acetone (5 mL) was heated to reflux for 16 h. The reaction mixture was cooled to room temperature. The precipitate was filtered and treated with dilute ammonia. Precipitate was filtered, washed with water, and dried under reduced pressure to yield 2-(5-chloro-2,4- dimethoxyphenyl)imidazo[l,2-a]pyrimidin-7-amine 158b ( 95 mg, 36%) as a white solid. 1H NMR (300 MHz, DMSO-d6) delta 8.36 (d, 1H J = 7.2Hz), 8.09 (s, 1H). 7.76 (s, IH), 6.84 (s, IH), 6.76 (s, 2H), 6.22 (d, 1H, J = 7.2Hz), 3.98 (s, 3H), 3.92 (s, 3H); ESI MS m/z 305 [M+H]+

Statistics shows that 156-81-0 is playing an increasingly important role. we look forward to future research findings about Pyrimidine-2,4-diamine.

Reference:
Patent; ONCOTHERAPY SCIENCE, INC.; MATSUO, Yo; HISADA, Shoji; NAKAMURA, Yusuke; CHAKRABARTI, Anjan; RAWAT, Manish; RAI, Sanjay; SATYANARAYANA, Arvapalli, Venkata; DUAN, Zhiyong; TALUKDAR, Arindam; RAVULA, Srinivas; DECORNEZ, Helene; (491 pag.)WO2017/58503; (2017); A1;,
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Pyrimidine – Wikipedia

705-24-8, 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 705-24-8 as follows.

To a solution of 1 -methylpiperidin-4-ol (35 mg, 0.30 mmol) in THF (0.5 mL) at 0C was added 60% NaH (12 mg, 0.30 mmol). After the mixture was stirred for 20 minutes, a solution of Intermediate 2 (42 mg, 0.10 mmol) in THF (0.5 mL) was added. Then the ice bath was removed, and the reaction mixture was stirred at room temperature for two hours. The reaction was quenched by water (0.1 mL), and concentrated. The residue was purified directly by MS-HPLC to afford Compound 39 (18 mg, 35%). LCMS (method A): m/z 503.4 (M+H)+. ‘H NMR (CDCI3) delta 8.50 (s, 1H), 77.44 (d, 2H), 7.17 (d, 2H), 5.72 (d, 1H), 5.31 (m, 1H), 4.60 (br, 1H), 3.60 (m, 1H), 3.40 (m, 2H), 3.24 (br, 1H), 3.03 (br, 2H), 2.92-2.77 (m, 4H), 2.40 (br, 1H), 2.25 (m, 3H), 2.1 1-1.88 (m,4H); Following procedure as described in Example 2, and replacing THF with DMF, piperidine-2,4-dione (249 mg, 2.20 mmol) was converted to Compound 3A. The crude material was purified by silica gel chromatography (0-90% EA/hexane) to afford Compound 3A (375 mg, 64%). LCMS (method A): m/z 294.3 (M+H)+. XH NMR (CDC13): delta 7.14 (s, 1H), 5.97 (br s, 1H), 5.83 (s, 1H), 3.60 (t, 2H), 2.72 (m, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,705-24-8, its application will become more common.

Reference:
Patent; VENENUM BIODESIGN LLC; HUANG, Chia-Yu; MCGUINNESS, Brian F; XU, Xiaoqing; KULTGEN, Steven G.; MCMASTER, Ellen Sieber; BEASLEY, James R.; (356 pag.)WO2018/5794; (2018); A2;,
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Pyrimidine – Wikipedia

588-36-3, 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. 588-36-3, name is 4-Amino-5-hydroxymethyl-2-(methylthio)pyrimidine. A new synthetic method of this compound is introduced below.

To a solution of (4-amino-2-(methylthio)pyrimidin-5 -yl)methanol (11 g, 63 mmol, 1.0 equiv) in CHC13 (900 mL) was added Mn02 (43.85 g, 504 mmol, 8.0 equiv). The suspension was stirred overnight at rt. The resulting mixture was filtration and washing with CHC13. The filtrate was concentrated under vacuum to give 10 g (94%) of 4-amino-2-(methylthio)pyrimidine-5- carbaldehyde as a white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,588-36-3, 4-Amino-5-hydroxymethyl-2-(methylthio)pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; PRINCIPIA BIOPHARMA, INC.; VERNER, Erik; BRAMELD, Kenneth Albert; WO2015/120049; (2015); A1;,
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Pyrimidine – Wikipedia

130049-82-0, Adding a certain compound to certain chemical reactions, such as: 130049-82-0, 3-(2-Chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidine-4-one, 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, 130049-82-0, blongs to pyrimidines compound.

79 g of 6-Fluoro-3-(4- piperidinyl)-l,2-benzisoxazole hydrochloride, 375 ml of methanol, and 78.2 g of triethyl amine were charged in a reaction vessel at 25-300C. The reaction mixture was stirred for 5 minutes. 75 g of the compound of formula II and 375 ml methanol were added to the above mass. The reaction mixture was heated to 60-630C and then maintained at 60-630C to achieve the desired conversion. The reaction mixture was then cooled to 40-450C. Methanol was distilled off under reduced pressure up to two volumes. 375 ml of water was added to the reaction mixture and stirred for 20-30 minutes at 25-300C. The solid was filtered and washed twice with 150 ml water followed by 2×150 ml acetone to obtain 87 g crude paliperidone. (Purity of compound of formula I >97%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,130049-82-0, its application will become more common.

Reference:
Patent; WATSON PHARMA PRIVATE LIMITED; WO2009/116071; (2009); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

109-12-6, 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 109-12-6, name is Pyrimidin-2-amine. This compound has unique chemical properties. The synthetic route is as follows.

A 5 L three-necked round bottom flask was charged with 2-aminopyrimidine (285.30 g, 3 mol), N-bromosuccinimide (1.17 kg, 6.6 mol), acetonitrile 2 L and methanol 1 L. The mixture in the reaction flask was stirred at 70 C for 6 hours. TLC and HPLC confirmed the reaction was complete. After the reaction was completed, the solvent was removed by rotary evaporation to give the crude product. The crude product was concentrated by evaporation and recrystallized to give the pure product 2-amino-5-bromopyrimidine. After drying, the yield was 90.48% and the purity was 99.05% (HPLC).

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 109-12-6, Pyrimidin-2-amine.

Reference:
Patent; Shandong Youbang Biochemical Technology Co., Ltd.; Geng Xuanping; Zhang Xianglong; Cheng Wei; Lai Xinsheng; Lai Chao; Lai Ziteng; (4 pag.)CN106632079; (2017); A;,
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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. 109-12-6, name is Pyrimidin-2-amine. This compound has unique chemical properties. The synthetic route is as follows. 109-12-6

The 2-aminopyrimidine (2.5g, 26.29mmol) was dissolved in acetonitrile (25mL) was added N- bromosuccinimide (4.6g, 27.9mmol) under ice-cooling, stirred in the dark overnight at room temperature. Recovery of the solvent under reduced pressure, washed with water (100 mL) was washed, filtered off with suction, and dried in vacuo to give a white solid. Yield: 97%

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, 109-12-6, Pyrimidin-2-amine.

Reference:
Patent; Zhejiang University; Shanghai Institute of Materia Medica, Chinese Academy of Sciences; Liu, Tao; Li, Jia; Hu, Yongzhou; Gao, Anhui; Dong, Xiaowu; Zhou, Yubo; Song, Pinrao; Tong, Lexian; (59 pag.)CN106588884; (2017); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

The common heterocyclic compound, 147118-40-9, name is Rosuvastatin methyl ester, molecular formula is C23H30FN3O6S, 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. 147118-40-9

Example 3 Methyl (E)-(6-[2-[4-(4-fluorophenyl)-6-isopropyl-2-[methyl-(methylsulfonyl)ainino]- rhoyrimidin-5-yl]vmyl](4i?,65)-2,2-dimethyl-[l,3]dioxan-4-yl)-acetate IX; Methyl ester IX (1.07 g) was dissolved in acetone (5.5 ml) and dimethoxypropane (5.5 ml). P- toluenesulfonic acid (0.1 g) was then added, and the mixture was stirred at room temperature for 1.5 hours. Then, alkalization with triethylamine (0.12 ml) was carried out, and the solution was evaporated. After adding ethyl acetate (60 ml), the mixture was shaken with water (2 x 8 ml). The organic layer was dried with Na2SO4 and evaporated. The crude product was crystallized from isopropyl alcohol. 0.88 g of white crystals of acetonide IX was obtained, which were recrystallized from isopropyl alcohol.1H NMR (CDCl3) delta: 7.62 (m, 2H); 7.08 (m, 2H); 6.52 (dd, IH, //=16.21, /2=1.30); 5.45 (dd, IH, //=16.23, J2=5.36); 4.45 (m, IH); 4.35 (m, IH); 3.70 (s, 3H); 3.56 (s, 3H); 3.51 (s, 3H); 3.37 (sept, IH, /=6.68); 2.56 (dd, IH, //=15.68, J2=6.71); 2.38 (dd, IH, //=15.69, /2=6.39); 1.49 (s, 3H); 1.40 (s, 3H); 1.68 (m, IH); 1.27 (d, 3H, J=6.69); 1.23 (d, 3H, J=6.66).

The synthetic route of 147118-40-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ZENTIVA, a.s.; WO2007/121; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia