Pyrimidines

Synthetic Route of 767-15-7, 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. 767-15-7, name is 2-Amino-4,6-dimethylpyrimidine. A new synthetic method of this compound is introduced below.

2-Amino-5-bromo-4,6-dimethylpyrimidine (3):; To a stirred solution containing 4.3 lg (34.75 mmol) of 2-amino-4,6-dimethylpyrimidine (2) in 150 mL of acetonitrile were added 6.15g (52.12 mmol) of N-bromosuccinimide. The reaction mixture was stirred at room temperature under argon atmosphere for 3 h. The formed precipitate was filtered and dried to afford the expected product as a white solid: yield 5.93g (83%).1H-NMR(CDC13) delta 5.19 (br, 2H), 2.44 (s, 6H);13C-NMR (CDC13) delta 166.28, 160.73, 109.60, 24.70.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,767-15-7, 2-Amino-4,6-dimethylpyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; ARIZONA BOARD OF REGENTS; HECHT, Sidney; ARMSTRONG, Jeffrey; KHDOUR, Omar; LU, Jun; ARCE, Pablo; WO2011/103536; (2011); A1;,
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Application of 131860-97-4, 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 131860-97-4, name is (E)-Methyl 2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyacrylate. This compound has unique chemical properties. The synthetic route is as follows.

Further screening experiments, using DMF as a solvent, were carried out as detailed below: Methyl (?)-2-{2-[6-chlororhoyrimidin-4-yloxy]ph.enyl}-3-methoxyacrylate (H) (6.4g of 45.2% strength solution in DMF) was charged to the reaction tube followed by further DMF (6.4 g), 2-cyanophenol (1.2g), potassium carbonate (1.5 mol equivalents) and the compound being tested as a catalyst (10 mol%). The reaction mixtures were held, with stirring, at 4O0C for 4hrs, then at 6O0C for 2 hrs. The reaction was monitored for loss of starting material and formation of product, throughout the hold periods, by Gas Chromatography. Results are recorded as area % levels of methyl (E)-2-{2-[6-chloropyrimidin-4-yloxy]phenyl}-3- methoxyacrylate (II) and methyl (2s)-2-{2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3- methoxyacrylate (I) in the reaction mixture.The following systems were tested:TABLE 3The results are shown in Table 4 below:; A stirred solution of (E)-2-{2-[6-chloropyrimidin-4-yloxy]phenyl}-3-methoxyacrylate (80.Og at 98%w/w, 0.24mols) in DMF (8Og) was heated to approximately 60C and then potassium carbonate (51.6g at 98%w/w, 0.37mols), 2-cyanophenol (32.8g at 97.5%w/w, 0.27mols) in DMF (32.8g) and quiniclidinone hydrochloride (2.03g at 97%w/w, 0.012mols were added at five minute intervals. The reaction mixture was heated to 800C and held at this temperature for 195 minutes when analysis indicated that the reaction was complete. The DMF was distilled off under vacuum to a final temperature of 100C and then toluene (134.8g) was charged, followed by hot water (259.4g), maintaining the temperature of the mixture above 7O0C. The mixture was stirred at 80C for 30 minutes, settled and then the aqueous phase separated. The toluene phase (226.4g) contained methyl (E)-2- {2-[6-(2- cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate (41.58%w/w) 95.8% of theory.

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 131860-97-4, (E)-Methyl 2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyacrylate.

Reference:
Patent; SYNGENTA LIMITED; WO2008/43977; (2008); A1;,
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Related Products of 761440-16-8 , The common heterocyclic compound, 761440-16-8, name is 2,5-Dichloro-N-(2-(isopropylsulfonyl)phenyl)pyrimidin-4-amine, molecular formula is C13H13Cl2N3O2S, 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 500L enamel reactor was added 80.6kg of isopropanol,12.4 kg of the compound 1-dihydrochloride obtained in Example 1 and 14.7 kg of the compound 3 obtained in Example 6,Heated to reflux, the reaction 24 hours. The reaction solution was cooled to 10 C, stirred for 3 hours,filter.The wet filtered product was added enamel reactor,99.2 kg of isopropanol and 13.0 kg of purified water were added,Reflux stir until solids are clear.Control temperature not lower than 85 ,99.2 kg of isopropanol was added dropwise.Slowly cooled to 20 ,Stir for 2 hours and filter.The wet filtered product was added to the enamel reactor again,Add 99.2 kg of isopropanol and 13.0 kg of purified water and stir under reflux until the solid is clear.Controlled at a temperature not lower than 85 C, 99.2 kg of isopropanol was added dropwise.Slowly cooled to 20 C, stirred for 2 hours, filtered, washed with isopropanol.The filtered wet product was vacuum dried at 55 C for 16 hours,A 16.4 kg yellow solid (Compound 4, ceritinib dihydrochloride) was obtained in a yield of 67% and a purity of 99.9%.

The synthetic route of 761440-16-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Xingtai Pharmaceutical Technology Co., Ltd.; Liu Xuejun; Hong Huiyi; Chen Xiaodong; (12 pag.)CN106854200; (2017); A;,
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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.1202759-91-8, name is N4-(3-Aminophenyl)-5-fluoro-N2-(4-(2-methoxyethoxy)phenyl)pyrimidine-2,4-diamine, molecular formula is C19H20FN5O2, molecular weight is 369.3928, as common compound, the synthetic route is as follows.category: pyrimidines

Weigh 29mgMonomethyl fumarate,84mg HATU, 30mg HOAT in a 25ml round bottom flask, add 1.6mlDCM, 0.4 ml DMF and 66 mul DIEA were used as solvents. After stirring at room temperature for about 10 minutes, 74 mg of the A1 intermediate was added to the reaction system. After stirring for about 1 hour at room temperature, 100 ml of saturated aqueous sodium bicarbonate solution was added, followed by 15 ml of DCM. The mixture was extracted 3 times and the organic phase was evaporated to dryness under reduced pressure. The residue was applied to a silica gel column with DCM_MeOH=70:1 (volume ratio) to obtain 60 mg of the compound represented by Formula I-2 in a yield of 62%

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1202759-91-8, N4-(3-Aminophenyl)-5-fluoro-N2-(4-(2-methoxyethoxy)phenyl)pyrimidine-2,4-diamine, and friends who are interested can also refer to it.

Reference:
Patent; Tsinghua University; Rao Yu; Liu Wanli; Yang Maojun; Sun Yonghui; (22 pag.)CN107973754; (2018); A;,
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Application of 6328-58-1, Adding some certain compound to certain chemical reactions, such as: 6328-58-1, name is 6-Methyl-2-(methylthio)-1H-pyrimidin-4-one,molecular formula is C6H8N2OS, 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 6328-58-1.

Propargyl bromide (2) (1.2 mmol, 0.10 mL) was added slowlyto a stirred mixture of 6-methyl-2-(methylthio)pyrimidine-4(3H)-one (1) (1.0 mmol, 0.15 g) and K2CO3 (2.0 mmol,0.27 g) in dry DMF (4 mL) at room temperature, and the mixturewas stirred at room temperature for 10 h. Upon completionof the reaction, the solvent was evaporated under vacuum,and the resulting residue was washed with water. The residuewas finally purified by flash column chromatography (hexane/ethyl acetate = 10:1) to give the titles compounds. Compound (3): TLC (hexane/ethyl acetate = 10:1)Rf = 0.7; yield 70%; white powder; m.p. 80-82 C; 1H NMR(300 MHz, CDCl3): delta 2.38 (s, 3H, CH3), 2.51 (t, J = 2.4 Hz,1H, CH), 2.56 (s, 3H, CH3), 5.00 (d, J = 2.4 Hz, 2H, CH2),6.30 (s, 1H, ArH); 13C NMR (75 MHz, CDCl3): delta 14.0,23.8, 53.6, 74.9, 78.1, 102.0, 167.9, 168.1, 171.3; IR (KBr):3167, 2925, 2116, 1581, 1404, 1339, 1041 cm-1. Anal.calcd for C9H10N2OS: C, 55.65; H, 5.19; N, 14.42; found:C, 55.82; H, 5.28; N, 14.58%.Compound (4): TLC (hexane/ethyl acetate = 10:1) Rf = 0.52;yield 30%; white powder; m.p. 122-124 C; 1H NMR(300 MHz, CDCl3): delta 2.15 (s, 3H, CH3), 2.20 (t, J = 2.4 Hz, 1H,CH), 2.53 (s, 3H, CH3), 4.76 (d, J = 2.4 Hz, 2H, CH2), 6.00(s, 1H, ArH); 13C NMR (75 MHz, CDCl3): delta 15.1, 23.8, 32.6,72.3, 107.6, 161.1, 161.3, 162.7; IR (KBr): 3124, 3001, 1645,1581, 1543, 1461 cm-1. Anal. calcd for C9H10N2OS: C, 55.65;H, 5.19; N, 14.42; found: C, 55.79; H, 5.11; N, 14.28%.

According to the analysis of related databases, 6328-58-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Rezaeimanesh, Fatemeh; Bakherad, Mohammad; Nasr-Isfahani, Hossein; Journal of Chemical Research; vol. 43; 9-10; (2019); p. 431 – 436;,
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Related Products of 374930-88-8, 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.374930-88-8, name is tert-Butyl 4-(5-bromopyrimidin-2-yl)piperazine-1-carboxylate, molecular formula is C13H19BrN4O2, molecular weight is 343.2196, as common compound, the synthetic route is as follows.

General procedure: In a dried microwave reactor vessel were added 3-bromoquinoline(0.204 mL, 1.5 mmol), Pd(dba)2 (86 mg, 0.15 mmol), K2CO3carbonate (415 mg, 3.00 mmol), S-Phos (185 mg, 0.45 mmol), dryD8-IPA (0.500 mL) and MeCN (1 mL). The mixture was degassedand placed under a nitrogen atmosphere. The sealed reaction tubewas heated to 100 C in a microwave (Biotage Initiator) for 2.5 h.The solvents were removed under reduced pressure, the crudematerial pre-loaded on to silica and purified using flash silica chromatography(15% EtOAc/heptane). The fractions containing thedesired compound were combined and evaporated to dryness toafford 3-deuterioquinoline (140 mg, 72%); 1H NMR (400 MHz,DMSO, 27 C): d (ppm) 7.62 (ddd, J = 1.20, 6.89, 8.11 Hz, 1H), 7.77(ddd, J = 1.50, 6.87, 8.43 Hz, 1H), 7.99 (dd, J = 1.33, 8.18 Hz, 1H),8.03 (d, J = 8.41 Hz, 1H), 8.37 (s, 1H), 8.91 (d, J = 1.70 Hz, 1H); 13CNMR (176 MHz, DMSO, 30 C) 121.0, 126.4, 127.8, 128.0, 128.8,129.3, 135.8, 147.7, 150.3; HRMS (EI): M+, found 130.0643,C9H6DN requires 130.0641.

The chemical industry reduces the impact on the environment during synthesis 374930-88-8, I believe this compound will play a more active role in future production and life.

Reference:
Article; Donald, Craig S.; Moss, Thomas A.; Noonan, Gary M.; Roberts, Bryan; Durham, Emma C.; Tetrahedron Letters; vol. 55; 22; (2014); p. 3305 – 3307;,
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Electric Literature of 58347-49-2, 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. 58347-49-2, name is 7-Chloropyrazolo[1,5-a]pyrimidine, molecular formula is C6H4ClN3, 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 Preparation of 7-(3,5-di-t-butyl-4-hydroxyphenyl)-aminopyrazolo[1,5-a]pyrimidine: A suspension of 7-chloropyrazolo[1,5-a]pyrimidine (1.0 g), 3,5-di-t-butyl-4-hydroxyaniline hydrochloride (1.8 g) and diethylaniline (2.3 ml) in toluene (50 ml) is heated at 120 C. for 30 minutes. After cooling, the solvent is distilled off, and the residue is purified by silica gel column chromatography (solvent; CHCl3) to give 7-(3,5-di-t-butyl-4-hydroxyphenyl)aminopyrazolo[1,5-a]pyrimidine (890 mg) as colorless crystal. M.p. 264-266 C. (decomposed) 1 H-NMR (CDCl3): delta 1.48 (s, 18H), 5.63 (s, 1H), 5.92 (s, 1H), 6.55 (d, J=2.3 Hz, 1H), 7.47 (s, 2H), 8.14 (d, J=2.3 Hz, 1H)

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 58347-49-2, 7-Chloropyrazolo[1,5-a]pyrimidine.

Reference:
Patent; Otsuka Pharmaceutical Factory, Inc.; US5688949; (1997); A;,
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Pyrimidine – Wikipedia

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. 1004-39-3, name is 4,6-Diaminopyrimidine-2-thiol, molecular formula is C4H6N4S, 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. name: 4,6-Diaminopyrimidine-2-thiol

Potassium hydroxide (88.8 g, 1.58 mol) and 4,6-diamino-2-mercaptopyrimidine (45.0 g, 316 mmol) were sequentially added to 230 ml of water and heated at 85 C. for 2 h.Add 220 ml of methanol, 1-bromo-3,3,3-trifluoropropane (280 g, 1.58 mol) and KI(2.63 g, 15.8 mmol), continued stirring at 60 C for 24 h. The reaction solution was concentrated under reduced pressure.After cooling to room temperature, the filter cake was dried to obtain 71.6 g of a yellow solid with a yield of 95%.

With the rapid development of chemical substances, we look forward to future research findings about 1004-39-3.

Reference:
Patent; Shanghai Pharmaceutical Industry Institute; China Pharmaceutical Industry Zongyuan; Li Jianqi; Lu Kuanying; Ma Zhilong; Jin Xunqi; Zhou Chao; (21 pag.)CN107973832; (2018); A;,
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Electric Literature of 62802-42-0, Adding some certain compound to certain chemical reactions, such as: 62802-42-0, name is 2-Chloro-5-fluoropyrimidine,molecular formula is C4H2ClFN2, 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 62802-42-0.

Preparation 152 N-[(4aR,7aR)-6-(5-Fluoropyrimidin-2-yl)-7a-isothiazol-5-yl-4,4-a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazin-2-yl]benzamide 5-Fluoro-2-chloropyrimidine (58 mL, 608.3 mol), and diisopropylethylamine (227 mL 1.30 mol, 227.3 mL) is added to N-[(4aR,7aR)-7a-isothiazol-5-yl-4-a,5,6,7-tetrahydro-4H-pyrrolo[3,4-d][1,3]thiazin-6-ium-2-yl]benzamide chloride (174.2 g, 434.5 mol), in N-methylpyrrolidone (1.4 L) at 22 C. and stirred. The reaction is heated at 100 C. for 4 hours and then cooled to room temperature. The crude mixture is added to water (14 L) and then stirred 1 hour. A white solid is collected by filtration and dried under vacuum to constant weight. The crude product is purified by silica gel chromatography, eluting with ethyl acetate: methylene chloride (3/1) to give the title compound (139 g, 72%). ES/MS (m/e): 441.0 (M+H).

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. 62802-42-0, 2-Chloro-5-fluoropyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Eli Lilly and Company; BECK, James Peter; GREEN, Steven James; LOPEZ, Jose Eduardo; MATHES, Brian Michael; MERGOTT, Dustin James; PORTER, Warren Jaye; RANKOVIC, Zoran; SHI, Yuan; WATSON, Brian Morgan; WINNEROSKI, JR, Leonard Larry; US2013/261111; (2013); A1;,
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Adding a certain compound to certain chemical reactions, such as: 4316-98-7, 6-Chloro-4,5-diaminopyrimidine, 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, Application In Synthesis of 6-Chloro-4,5-diaminopyrimidine, blongs to pyrimidines compound. Application In Synthesis of 6-Chloro-4,5-diaminopyrimidine

1.6 g of the 2-(N-methylmethylsulfonamide)nicotinic acid obtained in this way are suspended in 10 ml of dichloromethane, and 0.6 ml of thionyl chloride is added dropwise. This suspension is stirred at 40 C. for 3 h, and, immediately after addition of a few drops of DMF, 3 is reacted further with 1 g of 6-chloropyrimidine-4,5-diamine at RT for 16 h. Removal of the solvent gives a 1:3 mixture of 2.3 g of the regioisomers 4, which are immediately reacted further in 30 ml of POCl3 at 50 C. in 48 h to give 5. Chromatography with dichloromethane/methanol=100:0->90:10 gives 810 mg of a colourless solid; LCMS: 339.0 (M+H), RT. 1.341 min.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,4316-98-7, 6-Chloro-4,5-diaminopyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; MERCK PATENT GMBH; Heinrich, Timo; Rohdich, Felix; Esdar, Christina; Krier, Mireille; Greiner, Hartmut; US2015/218155; (2015); A1;,
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