Pyrimidines

Reference of 353272-15-8, 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. 353272-15-8, name is 6-Chloro-5-iodopyrimidin-4-amine, molecular formula is C4H3ClIN3, 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.

To a mixture of (5 -2-(l-amiiioethyl)-5-chloro-3-cyclopropylquinazolin-4(3H)- one (50 mg, 0.189 mmoi ), 6-chloro-5-iodopyrimidin-4-amine (48 mg, 0.189 mmoi) and DIPEA (49 mg, 0.379 mmoi) in n-BuOH (1 mL) was heated to reflux and stirred further for 16 hours, then cooled to rt, and concentrated in vacuo. The residue was purified by a silica gel column chromatography (DCM/MeOH (v/v) = 100/1 ) to give the title compound as a yellowish solid (49 mg, yield 53%). MS (ESI, pos. ion) m/z: 483.0 [M+H]+; FontWeight=”Bold” FontSize=”10″ H NMR (400 MHz, CDC13) delta (ppm): 7.98 (s, 1H), 7.55-7.53 (m, 2H), 7.43-7.41(dd, J = 3.6, 5.6 Hz, 1H), 6.41-6.39 (d, J= 7.8 Hz, 1H), 6.12-6.05 (m, 1H), 5.04 (s, 2H), 3.05-3.03 (m, 1H), 1.59- 1.57 (d, J= 6.2 Hz, 3H), 1.43-1.41 (m, 2H), 1.14-1.10 (m, 1H), 0.95-0.86 (m,lH).

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 353272-15-8, 6-Chloro-5-iodopyrimidin-4-amine.

Reference:
Patent; CALITOR SCIENCES, LLC; SUNSHINE LAKE PHARMA CO., LTD.; XI, Ning; WANG, Liang; WANG, Tingjin; WU, Weibin; (123 pag.)WO2015/175579; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
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 90914-41-3, name is 3-Bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C5H2BrClN4

Bromopyrazolopyrimidine (8) To a 25 mL recovery flask were added 6 (230 mg, 0.708 mmol, 1.05 eq.), THF (10 mL), Et3N (470 muL, 3.37 mmol, 5.0 eq.), and chloropyrazolopyrimidine 7 EPO (157 mg, 0.674 mmol, 1.0 eq.). The reaction mixture was stirred at reflux for 1.5h. The reaction was concentrated and diluted with EtOAc (50 mL) and NaHCO3 (sat’d aq., 50 niL). The organic layer was washed with H2O (50 mL) and brine (50 mL). The combined aqueous layers were extracted with EtOAc (2 x 50 mL). The combined organic layers were dried over anhydrous Na2SO4, filtered, and concentrated to give a light-brown oil that slowly solidified to a white solid (308 mg crude). The crude material was purified via flash chromatography (10% to 20% CH3OH/CH2C12) to give a colorless oil (205 mg, 58%).Observed M+H: 523.1 (Br isotope)NMR, DMSO-d6, HCl salt : deltaltheta.40 (s, IH), 8.30 (s, IH), 7.49 (d, 2H), 7.26 (d, 2H), 4.88 (s, IH), 4.59 (m, 2H), 4.50 (obs m, 2H), 3.34-3.23 (m, 4H), 3.07-3.03 (m, 2H), 2.73 (s, 6H), 1.94 (d, 2H), 1.38-1.34 (m, 2H) ppm.

With the rapid development of chemical substances, we look forward to future research findings about 90914-41-3.

Reference:
Patent; EXELIXIS, INC.; WO2006/71819; (2006); A1;,
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Synthetic Route of 3680-71-5 , The common heterocyclic compound, 3680-71-5, name is 1,7-Dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one, molecular formula is C6H5N3O, 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 1: Preparation of 5-bromo-3H-pyrrolo[2,3-d]pyrimidin-4(7H)-one: (0344) [00156] To a stirred solution of 3H-pyrrolo[2,3-d]pyrimidin-4(7H)-one (5.5 g, 40.7 mmol) in N,N-dimethyl formamide (100 mL), N-(bis-trimethylsilyl)acetonitrile(18.22 g, 89.55 mmol) and N-bromo succinimide (7.24 g, 40.7 mmol) were added and the reaction mixture was stirred at room temperature for 2 h. The reaction mixture was quenched with cold water (1000 mL) and stirred for 30 minutes. The precipitated solid was filtered and dried under suction to afford title compound 5-bromo-3H-pyrrolo[2,3-d]pyrimidin-4(7H)-one (6.26 g, crude) as brown solid. Calculated (M+H): 213.9; Found (M+H): 214.0

The synthetic route of 3680-71-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LUC THERAPEUTICS; ANDERSON, David, R.; VOLKMANN, Robert, A.; MENNITE, Frank, S.; FANGER, Christopher; (390 pag.)WO2017/100591; (2017); A1;,
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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. 14001-67-3, name is 5-Bromo-2-methylthiopyrimidine, molecular formula is C5H5BrN2S, 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. Quality Control of 5-Bromo-2-methylthiopyrimidine

Step 1: 2-Methylsulfanyl-5-phenylethynyl-pyrimidine Bis-(triphenylphosphine)-palladium(II)dichloride (120 mg, 0.16 mmol, 0.05 equiv.) were dissolved in 50 ml THF and 5-bromo-2-methylsulfanyl-pyrimidine (840 mg, 4.1 mmol) and phenylacetylene (410 mu, 4.1 mmol, 1 equiv.) were added at room temperature. Triethylamine (1.36 ml, 12.3 mmol, 3 equiv.), triphenylphosphine (28 mg, 0.12 mmol, 0.03 equiv.) and copper(I)iodide (19 mg, 0.08 mmol, 0.03 equiv.) were added and the mixture was stirred for 3 hours at 65C. The reaction mixture was cooled and extracted once with saturated NaHCC”3 solution and three times with ethyl acetate. The organic layers were combined, dried with sodium sulfate, filtered and evaporated to dryness. The crude product was purified by flash chromatography on silicagel (heptane: ethyl acetate 100:0 -> 50:50). The desired 2- Methylsulfanyl-5-phenylethynyl-pyrimidine was obtained as a light yellow solid (400 mg, 44%), MS: m/e = 227.3 (M+H+).

With the rapid development of chemical substances, we look forward to future research findings about 14001-67-3.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; JAESCHKE, Georg; LINDEMANN, Lothar; RICCI, Antonio; RUEHER, Daniel; STADLER, Heinz; VIEIRA, Eric; WO2013/50460; (2013); A1;,
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Synthetic Route of 6623-81-0 , The common heterocyclic compound, 6623-81-0, name is 2,4-Dihydroxy-5-methoxypyrimidine, molecular formula is C5H6N2O3, 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 solution of compound 104 (2.8 g, 20 mmol) in dry acetonitrile (30 ml_) was added BSA (21 g, 1 00 mmol, 5 eq). The reaction mixture was stirred at 60 C for 4 h and cooled to room temperature. To this reaction mixture were added compound 1 03 (1 0.1 g, 20 mmol), TMSOTf (10.8 m l_, 60 mmol, 3eq), and the resulted reaction mixture was stirred at 60 C for 4 h. Upon completion of the reaction as monitored by TLC, the reaction mixture was treated with methylene chloride and saturated sodium bicarbonate. The organic phase was separated, and the aqueous phase was extracted with dichloromethane. The combined organic phase was dried over anhydrous Na2S04. The drying agent was filtered off, and the filtrate was concentrated under reduced pressure. The crude product was purified by flash chromatography on a silica gel column giving 1 1 g desired compound 105 in 95% yield.

The synthetic route of 6623-81-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MODERNA THERAPEUTICS, INC.; ROY, Atanu; CONLEE, Christopher, R.; DE FOUGEROLLES, Antonin; FRALEY, Andrew, W.; WO2014/93924; (2014); A1;,
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Adding a certain compound to certain chemical reactions, such as: 1979-96-0, 4,6-Dichloro-2-(methylthio)-5-nitropyrimidine, 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, Safety of 4,6-Dichloro-2-(methylthio)-5-nitropyrimidine, blongs to pyrimidines compound. Safety of 4,6-Dichloro-2-(methylthio)-5-nitropyrimidine

To a solution of compound 801 (2.46 g, 10.2 mmol) in THF (34 mL) at -20 C. was added Et3N (3.14 mL, 22.5 mmol) followed by a solution of NH3 (2.0 M in MeOH, 5.4 mL, 11 mmol). The mixture was stirred while warming to 0 C. for 1.5 h (LC/MS indicated consumption of starting materials). The reaction mixture containing compound 802 was taken forward without work-up.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1979-96-0, 4,6-Dichloro-2-(methylthio)-5-nitropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; GILEAD SCIENCES, INC.; Delaney, William E.; Link, John O.; Mo, Hongmei; Oldach, David W.; Ray, Adrian S.; Watkins, William J.; Yang, Cheng Yong; Zhong, Weidong; US2013/273005; (2013); A1;,
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Related Products of 22536-63-6 , The common heterocyclic compound, 22536-63-6, name is 2-Chloro-4-methoxypyrimidine, molecular formula is C5H5ClN2O, 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.

2.6 g of 6 (0.018 mol, 1 equiv), 1.3 g of compound 4(0.009 mmol, 0.5 equiv), 1.5 ml of 37% concd HCl (0.018 mol,1 equiv) were added in 10%, aqueous ethanol solution (25 ml)and heated at 80 C for 12 h. After that, the reaction mixturewas cooled to room temperature. The resulting precipitate wasfiltered, washed with mixture of water and ethanol, dried in vacuoat 40 C, and the obtained solid was purified by recrystallizationwith a mixture of water/ethanol to afford 2.3 g productas a white solid with the yield of 49%. Mp: 182-184 C, 1HNMR (400 MHz, DMSO-d6) d ppm: 3.93 (s, 3H, -OCH3), 6.29 (d,1H, J = 5.6 Hz, Pyrm-H), 7.14-7.19 (m, 2H, Ph-H), 7.60 (d, 1H,J = 1.2 Hz, Ph-H); 8.20 (d, 1H, J = 5.6 Hz, Pyrm-H), 9.55 (s, 1H,OH), 10.00 (s, 1H, NH); 13C NMR (100 MHz, DMSO-d6) d ppm:53.99 (-OCH3), 99.10, 107.53, 111.46, 112.37, 129.67, 140.74,153.22, 158.73, 160.04, 169.92; ESI-MS: 252.3 [M+H]+, 254.1[M+3]+, 274.6 [M+Na]+. C11H10ClN3O2 [251.67].

The synthetic route of 22536-63-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Rai, Diwakar; Chen, Wenmin; Tian, Ye; Chen, Xuwang; Zhan, Peng; De Clercq, Erik; Pannecouque, Christophe; Balzarini, Jan; Liu, Xinyong; Bioorganic and Medicinal Chemistry; vol. 21; 23; (2013); p. 7398 – 7405;,
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Pyrimidine – Wikipedia

Electric Literature of 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.

An oven-dried round bottom flask (10 ml) was charged with 0.1ml dimethylformamide solution of complex IV (0.1 mol % for aryl bromides and 0.2 mol % for aryl chlorides), aryl boronic acid (1.2 mmol), aryl halide (1.0 mmol), K2CO3 (1.5 mmol), TBAB (1.0 mmol) and 2 ml water. The reaction mixture was then heated (to 70 C for aryl bromides and 90 C for aryl chlorides) with stirring under aerobic conditions for the required time. At the end of the reaction, the reaction mixture was cooled to room temperature and extracted with ethyl acetate (2×5 ml). The combined extract was washed with water (2×10 ml), dried over anhydrous sodium sulfate and then subjected to GC-MS analysis for identification and yield determination (from the areas under the peaks) of the products. In the case of reactions with 2-naphthylboronic acid, the combined extract was evaporated to dryness under reduced pressure and the residue was purified by column chromatography (silica gel, ethyl acetate/n-hexane) to afford the coupling products. The products were identified by 1H and 13C NMR and HR-MS analysis.

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 1722-12-9, 2-Chloropyrimidine.

Reference:
Article; Babu, G. Narendra; Pal, Samudranil; Tetrahedron Letters; vol. 58; 10; (2017); p. 1000 – 1005;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 113583-35-0, 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. 113583-35-0, name is 2-Methanesulfonyl-4,6-dimethoxypyrimidine, molecular formula is C7H10N2O4S, 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 3 (Process A) Preparation of ethyl 4-(4,6-dimethoxypyrimidin-2-yloxy)-2-methylthiomethylthiophene-3-carboxylate (Compound No. 170) 50 ml of N,N-dimethylformamide was added to 3.5 g (15.1 mmol) of ethyl 4-hydroxy-2-methylthiomethylthiophene-3-carboxylate, 3.3 g (15.1 mmol) of 4,6-dimethoxy-2-methylsulfonylpyrimidine and 2.1 g (15.2 mmol) of potassium carbonate, and the mixture was heated and stirred at from 90 to 100 C. for 2 hours. After cooling, the reaction solution was poured into water, extracted with ethyl acetate, washed with water and a saturated sodium chloride aqueous solution, and then dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure, and the residue was purified by column chromatography to obtain 2.8 g (yield: 50.0%) of the desired product.

According to the analysis of related databases, 113583-35-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Kumiai Chemical Industry Co., Ltd.; Ihara Chemical Industry Co., Ltd.; US5527763; (1996); A;,
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. 1059735-34-0, name is 7-Benzyl-2,4-dichloro-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine. A new synthetic method of this compound is introduced below., Product Details of 1059735-34-0

A mixture of 7-benzyl-2,4-dichloro-6,8- dihydro-5H-pyrido[3,4-d] pyrimidine (3.00 g, 10.2 mmol, 1.00 eq), l-tert-butyl-3 -methyl piperazine-l,3-dicarboxylate (2.62 g, 10.7 mmol, 1.05 eq), DIEA (3.30 g, 25.5 mmol, 4.45 mL, 2.50 eq) in DMSO (50.0 mL) was degassed and purged with nitrogen 3 times. The mixture was stirred at 100 C for 12 hours under a nitrogen atmosphere. The reaction mixture was diluted with DCM (200 mL), washed with brine (3 50 mL), dried over Na2S04, filtered and concentrated under reduced pressure to dryness. The residue was purified by column chromatography (Si02, Petroleum ether/Ethyl acetate = 10: 1 to 3 : 1) to give 1-tert-butyl 3- methyl 4-(7-benzyl-2-chloro-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-yl)piperazine-l,3- dicarboxylate (2.10 g, 3.81 mmol, 37.4 % yield, 91.0 % purity) as a yellow oil. ESI MS m/z 502.1 [M+H]+.

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, 1059735-34-0, 7-Benzyl-2,4-dichloro-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine.

Reference:
Patent; MIRATI THERAPEUTICS, INC.; ARRAY BIOPHARMA, INC.; FISCHER, John, P.; FELL, Jay, Bradford; BLAKE, James, F.; HINKLIN, Ronald, Jay; MEJIA, Macedonio, J.; HICKEN, Erik, James; CHICARELLI, Mark, Joseph; GAUDINO, John, J.; VIGERS, Guy, P.A.; BURGESS, Laurence, E.; MARX, Matthew, Arnold; CHRISTENSEN, James, Gail; LEE, Matthew, Randolf; SAVECHENKOV, Pavel; ZECCA, Henry, J.; (529 pag.)WO2017/201161; (2017); A1;,
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