Pyrimidines

Electric Literature of 4316-93-2, 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 4316-93-2, name is 4,6-Dichloro-5-nitropyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

6-Chloro-5-nitropyrimidin-4-amine[00161] A solution of 28% aqueous ammonium hydroxide (670 mL, 5.35 mol, 1.04 equiv) was added in a drop-wise fashion to a rapidly stirred solution of the 4,6-dichloro-5- nitropyrimidine solid (1000 g, 5.16 mol, 1.00 equiv) in diethyl ether (4000 mL) and methanol (670 mL). The addition was carried out over a period of 2 hours. Upon completion of addition, the resulting yellow solid was filtered off, washed with water and hexane, and dried under reduced pressure to give the title compound as a yellow solid (yield: 675 g). This crude solid was used in the next step without any further purification. NMR (400 MHz, DMSO- d6): delta 8.97 (s, 1H), 7.91 (broad s, 2H). MS (EI) for C4H3CIN4O2: 175 (MH+).

According to the analysis of related databases, 4316-93-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; EXELIXIS, INC.; PATRICK, Kearney; WO2012/37226; (2012); A1;,
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Pyrimidine – Wikipedia

Application of 5751-20-2 , The common heterocyclic compound, 5751-20-2, name is 2-(Methylthio)pyrimidin-4(3H)-one, molecular formula is C5H6N2OS, 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.

Step 2, Preparation of 5-bromo-2-methylthio-4-pyrimidinone: Take 142 g of 2-methylthio-4-pyrimidinone, dissolve in 500 ml of methylene chloride, add NBS 190 g, reflux for 6 hours, After the reaction is completed, cool to room temperature, filter, wash the filtrate, organicThe phase was dried and recrystallized on an ice bath to give 190 g of a pale yellow solid in a yield of 87percent.

The synthetic route of 5751-20-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Weiju Industrial Co., Ltd.; Liu Hui; (6 pag.)CN107488175; (2017); A;,
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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 5305-59-9, name is 6-Chloropyrimidin-4-amine. This compound has unique chemical properties. The synthetic route is as follows. category: pyrimidines

The 400mg4-amino-6-chloro-pyrimidine, 1.51g (1.5equiv) adding cesium carbonate flask, 10mLN, N ‘-dimethyl formamide as a solvent, adding 405 mu L (1.5equiv) morpholine, heating to 100 C, reaction 12h. Adding proper amount of water, extraction with ethyl acetate, saturated salt water washing, drying by anhydrous sodium sulfate, filter, evaporate solvents under reduced pressure, the residue is purified by silica gel column chromatography separation, methanol/dichloromethane = 1/50 elution, to get the yellow solid 245 mg, yield 44%.

With the rapid development of chemical substances, we look forward to future research findings about 5305-59-9.

Reference:
Patent; East China University of Technology; Mao, Fei; Wang, Huan; Li, Xiaokang; Zhang, Haiyan; Lu, Zhengyu; Li, Jian; (43 pag.)CN105418592; (2016); A;,
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Synthetic Route of 1060816-58-1, Adding some certain compound to certain chemical reactions, such as: 1060816-58-1, name is 5-Bromo-2-chloro-7H-pyrrolo[2,3-d]pyrimidine,molecular formula is C6H3BrClN3, 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 1060816-58-1.

To a stirred solution of 5-bromo-2-chloro-7H-pyrrolo[2,3-d]pyrimidine (3.0 g, 12.9 mmol), cyclohexanol (2.59 g, 25.9 mmol) and PPh3 (8.46 g, 32.3 mmol) in THF (100 mL) was added DEAD (5.62 g, 32.3 mmol) dropwise at 0 C. The resulting solution was stirred for 16 h at room temperature under nitrogen atmosphere. The resulting solution was condensed under reduced pressure. The residue was purified by reversed phase flash chromatography with the following conditions: Column: WelFlash TM C18-I, 20-40 um, 330 g; Eluent A: Water (plus 10 mmol/L TEA); Eluent B: ACN; Gradient: 70% – 90% B in 25 min; Flow rate: 80 mL/min; Detector: UV 200/220 nm; desired fractions were collected at 78% B and concentrated under reduced pressure to afford 5-bromo-2-chloro-7-cyclohexyl-7H-pyrrolo[2,3-d]pyrimidine (1.7 g, 42%) as a white solid.1H NMR (400 MHz, DMSO-d6) d 8.84 (s, 1H), 8.11 (s, 1H), 4.67-4.49 (m, 1H), 1.96-1.64 (m, 7H), 1.47 (q, J = 13.5 Hz, 2H), 1.32-1.12 (m, 1H). LC/MS (ESI, m/z): [(M + 1)]+ = 313.95, 315.95

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. 1060816-58-1, 5-Bromo-2-chloro-7H-pyrrolo[2,3-d]pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; KYMERA THERAPEUTICS, INC.; JI, Nan; MAINOLFI, Nello; WEISS, Matthew; (977 pag.)WO2020/10210; (2020); A1;,
Pyrimidine | C4H4N2 – PubChem,
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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. 1558-17-4, name is 4,6-Dimethylpyrimidine, the common compound, a new synthetic route is introduced below. Quality Control of 4,6-Dimethylpyrimidine

Example 24, 25 To a solution of 4,6-dimethylpyrimidine (1.08 g, 10 mmol) in THF (40 ml) was added dropwise at -78 C a solution of n-butyllithium. To the solution was added benzylbromide (1.71 g, 10 mmol). The mixture waswarmed up to 0 C and stirred for 30 minutes. To the reaction mixture was added an aqueous solution of ammonium chloride. The mixture was extracted with ethyl acetate, washed with water, dried and concentrated. The obtained residue was chromatographed on silica gel (n-hexane-ethyl acetate). The obtained fraction was concentrated to give 4-methyl-6-phenethylpyrimidine (1.7 g). Compound (I-24) and (I-25) were prepared from the above-obtained 4-methyl-6-phenethylpyrimidine in accordance with Example 2 and 3. Compound (I-24) 1H-NMR(CDCl3) delta: 1.40(3H,t,J=7.1Hz), 3.06(4H,s), 4.35(2H,q,J=7.1Hz), 6.39(1H,s), 6.86(1H,s), 7.12-7.35(6H,m), 8.95(1H,s). Compound (1-25) 1H-NMR(d6-DMSO) delta: 3.00(4H,s), 6.29(1H,s), 7.15-7.40(6H,m), 8.92(1H,s).

The synthetic route of 1558-17-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SHIONOGI & CO., LTD.; EP1219607; (2002); A1;,
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Synthetic Route of 13162-26-0, 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. 13162-26-0, name is 2,4-Dichloro-6-methyl-5-nitropyrimidine. A new synthetic method of this compound is introduced below.

Step A: 4-(4-bromo-2,6-dimethylphenoxy)-2-chloro-6-methyl-5-nitropyrimidine; A solution of LiHMDS in THF (1M, 77 ml, 77 mmol) was added at -78 C. to a mixture of 2,6-dimethoxy-4-bromophenol (14.07 g, 70 mmol) in THF (100 ml) over 15 minutes. The mixture was stirred for an additional 2 hours. Phenoxide salt was observed as solid suspension. The mixture was cooled with liquid nitrogen to a temperature around -100 C. and then a solution of 2,6-dichloro-4-methyl-5-nitropyrimidine (17.47 g, 84 mmol) in THF (50 ml) was added rapidly to the mixture, which turned dark red. The reaction was kept at a temperature around -100 C. for 1 hour. After warming to room temperature, the mixture was filtered and the solid was washed with ethanol to yield 16.75 g of the title product. The filtrate was concentrated and crystallized to obtain an additional 5.60 giving a total amount of 22.35 g of desired compound (60 mmol, 85%). 1H NMR (CDCl3, 400 MHz) delta 2.11 (s, 6H), 2.63 (s, 3H), 7.27 (s, 2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,13162-26-0, 2,4-Dichloro-6-methyl-5-nitropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Ardea Biosciences; US2009/162319; (2009); A1;,
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Pyrimidine – Wikipedia

Synthetic Route of 89793-12-4 , The common heterocyclic compound, 89793-12-4, name is Ethyl 2-chloropyrimidine-5-carboxylate, molecular formula is C7H7ClN2O2, 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.

Synthesis of Intermediate 4: Compound 2 (620 g, 1.0 equiv) and DIPEA (1080 g, 2.2 equiv. were dissolved in NMP (3100 ml) and stirred for 20 min. Compound 3 (680 g, 1.02 equiv.) was added and the reaction mixture was heated to about 85-95 °C for 4 hrs. The solution was allowed to slowly cool to r.t. This solution was poured onto H20 (20 L) and much of the solid was precipitated out from the solution with strong stirring. The mixture was filtered and the cake was dried under reduced pressure at 50 °C for 24 hr., yielding 896 g of compound 4 (solid, 86.8percent).

The synthetic route of 89793-12-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACETYLON PHARMACEUTICALS, INC.; VIB VZW; KATHOLIEKE UNVERSITEIT LEUVEN; LIFE SCIENCES RESEARCH PARTNERS VZW; JARPE, Matthew, Blaire; BENOY, Veronick; HELLEPUTTE, Lawrence, Van; VAN DEN BOSCH, Ludo; (50 pag.)WO2016/90230; (2016); A1;,
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Pyrimidine – Wikipedia

Related Products of 14160-93-1 ,Some common heterocyclic compound, 14160-93-1, molecular formula is C5H4ClN3O, 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.

A solution of 4-amino-6-chloropyrimidine-5-carbaldehyde (F1) (7.62 mmol, 1.2 g) was dissolved in a mixture of 25 ml of glacial acetic acid and 4 ml of water,Methoxyamine hydrochloride (13.71 mmol, 1.14 g) was added,The reaction was carried out at 25 C overnight.After completion of the reaction, 20 ml of water was added to the reaction mixture, and the mixture was extracted with 50 ml of ethyl acetate. The organic layer was washed with water 3 times, 10% sodium hydroxide solution and saturated brine, dried over anhydrous magnesium sulfate, The solvent was distilled off and purified by column chromatography (eluent petroleum ether: ethyl acetate = 3: 1) to give a white solid in 99% yield.

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. 14160-93-1, 4-Amino-6-chloropyrimidine-5-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Shan Dong University; Zhao, Guisen; Lu, Jinjie; Wang, Guanjie; Yang, Dezhi; Zhang, Zhen; Jing, Yongkui; (32 pag.)CN106045918; (2016); A;,
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Reference of 3680-69-1, Adding some certain compound to certain chemical reactions, such as: 3680-69-1, name is 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine,molecular formula is C6H4ClN3, 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 3680-69-1.

4-chloro-7H-pyrrolo2,3-dipyrimidine (2-E, 20.0g, 130.7mmol) dissolved in DCM (800 mL) was treated portion-wise with N-bromosuccinimide (26.7 g. 149.8 mmol), while maintaining the temperature around 25-30C. The reaction mixture was stirred at room temperature overnight. Water was added (500 mL) and the phases were separated. The organic phase was dried over NaSO4, filtered and concentrated in vacuo. The crude product was triturated in Et2O affording after filtration 5-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine as a white solid (2-F, 22.43 g, 74%).

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. 3680-69-1, 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARQULE, INC.; LAPIERRE, JEAN-MARC; EATHIRAJ, SUDHARSHAN; NAMDEV, NIVEDITA; SCHWARTZ, BRIAN; OTA, YUSUKE; MOMOSE, TAKAYUKI; TSUNEMI, TOMOYUKI; INAGAKI, HIROAKI; NAKAYAMA, KIYOSHI; (67 pag.)TW2017/22956; (2017); A;,
Pyrimidine | C4H4N2 – PubChem,
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Reference of 131860-97-4, 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.131860-97-4, name is (E)-Methyl 2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyacrylate, molecular formula is C15H13ClN2O4, molecular weight is 320.73, as common compound, the synthetic route is as follows.

Methyl (E)-2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxyacrylate (97.6 gm), 2-cyanophenol (36.9 gm), and potassium carbonate (25.4 gm) are added to, mixed, and dissolved in an aprotic solvent (241 gm) at room temperature. In this embodiment, the aprotic solvent is, for example, toluene. Then, 1-methylpyrrolidine (10.2 gm, 0.4 eq) is added as a catalyst, and stirred until uniform to form a basic mixture. Subsequently, the basic mixture is heated to 80 C., and reacted for 3 hrs. (0019) The basic mixture after reaction is subjected to a first distillation under a reduced pressure of 100 torr at 80 C., and the product left after the first distillation under reduced pressure is azoxystrobin. The distillate by the first distillation under reduced pressure is detected by gas chromatography (GC), and 1-methylpyrrolidine is determined to have a recovery rate of 96.3%. (0020) Azoxystrobin left after the first distillation under reduced pressure is added to the aprotic solvent (241 gm) and water (114 gm), mixed, and stirred until azoxystrobin is completely dissolved. After standing for layer separation, an upper first organic layer is collected, and then a lower aqueous layer is collected and further added with the aprotic solvent (15 gm). Next, an upper second organic layer is collected. The first organic layer and the second organic layer are combined, and detected by high performance liquid chromatography (HPLC) to show a yield of azoxystrobin of 94.9%. The combined organic layer is subjected to a second distillation under reduced pressure at 50-60 C. under 20-40 torr, to remove the solvent. This gives a crude product. The crude product is dissolved in methanol (156 gm) at 60 C., cooled to normal temperature and then to 5 C., and filtered to obtain a crystalline solid. The crystalline solid was washed with methanol (13 gm) and then dried at 50 C., to obtain purified azoxystrobin (112.9 gm) as a solid (yield 91.5%).

Statistics shows that 131860-97-4 is playing an increasingly important role. we look forward to future research findings about (E)-Methyl 2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyacrylate.

Reference:
Patent; SINON CORPORATION; CHEN, Chien-Hsing; HSIEH, Ming-Fang; LIN, Chih-Da; LIU, Chien-Yu; (4 pag.)US2020/165210; (2020); A1;,
Pyrimidine | C4H4N2 – PubChem,
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