Pyrimidines

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. 13223-25-1, name is 2-Chloro-4,6-dimethoxypyrimidine, molecular formula is C6H7ClN2O2, 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. Product Details of 13223-25-1

This example is used to describe the pyrimidine salicylic acid compounds of the present invention and processes for their preparation.1 mmol of Compound A was dissolved in 30 mL of re-evaporated toluene, 2 mmol of potassium carbonate was added, reacted at 20 C for 2 hours, 4,6-dimethoxy-2-methylsulfonylpyrimidine (1 mmol) was added and reacted at 120C for 12 h. The solvent was distilled off under reduced pressure, and a small amount of water was added to completely dissolve the solid. The aqueous layer was washed with ether several times. The aqueous layer was acidified with concentrated hydrochloric acid to pH=1, extracted with dichloromethane, dried over anhydrous sodium sulfate, Acid compound A1. The yield of compound A1 from compound A was 78% This example is used to describe the pyrimidine salicylic acid compounds of the present invention and processes for their preparation. The pyrimidine salicylic acid compound was prepared according to the method of Example 1, Except that 4,6-dimethoxy-2-methylsulfonylpyrimidine was replaced by 4,6-dimethoxy-2-chloropyrimidine to give pyrimidine salicylic acid compound A1. The yield of compound A1 from compound A was 15%.

With the rapid development of chemical substances, we look forward to future research findings about 13223-25-1.

Reference:
Patent; HUAZHONG NORMAL UNIVERSITY; YANG, GUANGFU; LIU, YUCHAO; CHEN, QIONG; CHEN, JIE; CUI, HAILAN; TANG, WEI; (17 pag.)CN104140397; (2016); B;,
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Synthetic Route of 1753-50-0, 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 1753-50-0, name is 2-Chloropyrimidine-5-carbonitrile. This compound has unique chemical properties. The synthetic route is as follows.

To a stirred solution of l-(4-fluorophenyl)ethan-1-amine (CN, 0.5 g, 3.59 mmol) in ethanol (10 mL), 2-chloropyrimidine-5-carbonitrile (AF, 0.55 g, 3.95 mmol) and DIPEA (3.0 mL, 17.9 mmol) were added and the reaction mixture was heated to 90C for 12 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was concentrated under reduced pressure. The crude product was purified by silica gel column chromatography using 20% EtOAc/hexane to afford compound CO (0.8 g, 91%) as a white solid. LC-MS: m/z 243.1 [M+H]+.

According to the analysis of related databases, 1753-50-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VPS-3, INC.; YATES, Christopher, M.; (397 pag.)WO2018/165520; (2018); A1;,
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Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 137281-39-1, 4-(2-(2-Amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl)benzoic acid, 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, Recommanded Product: 137281-39-1, blongs to pyrimidines compound. Recommanded Product: 137281-39-1

4. 4-[2-(2-Amino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoic acid (60 g 0.2 mol) Add to a 500ml four-neck bottle,Add 200ml of DMF and 60.6g of triethylamine to the temperature to 30 C and stir to dissolve.Benzyl chloride (0.2 mol) was added dropwise,Warming up to 50C for 1 hour,Evaporate DMF under reduced pressure,Add 200ml of pure water and stir.Adjust the pH to 5 with dilute hydrochloric acid, stir the crystallization,Cool down to 0-5C suction filtration,Drying the product 4-[2-(2-benzylamino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoic acid (molar Yield 95.8%, purity 99.0%)

The synthetic route of 137281-39-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Lunan Pharmaceutical Group Co., Ltd.; Zang Chao; Xia Mingjun; (11 pag.)CN110305136; (2019); A;,
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Related Products of 13036-57-2 ,Some common heterocyclic compound, 13036-57-2, molecular formula is C5H5ClN2, 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 suspension of 3-(5-aminopyrazin-2-yl)-6-cyclobutyl-2-fluorophenol (25 mg, 0.096 mmol), 2-chloro-4-methylpyrimidine (14 mg, 0.11 mmol), and K2CO3 (27 mg, 0.19 mmol) in DMSO (2 mL) was heated at 100 Celsius for 16 hours. The reaction was then cooled to room temperature, filtered, and the filtrate directly subjected to HPLC purification to give 5-{4-cyclobutyl-2-fluoro-3-[(4-methylpyrimidin-2-yl)oxy]phenyl}pyrazin-2-amine (15 mg, 45%). MS (ESI): mass calcd. for C19H18FN5O, 351.15; m/z found, 352.1 [M+H]+. 1H NMR (400 MHz, CDCl3) delta 8.37-8.33 (m, 1H), 8.26 (d, J=1.9, 2H), 7.81-7.75 (m, 1H), 7.26 (d, J=8.3, 1H), 7.00-6.97 (m, 1H), 3.75-3.63 (m, 1H), 2.52 (d, J=2.0, 3H), 2.27-2.09 (m, 4H), 2.04-1.92 (m, 1H), 1.87-1.76 (m, 1H).

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. 13036-57-2, 2-Chloro-4-methylpyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; Eccles, Wendy; Fitzgerald, Anne E.; Hack, Michael D.; Hawryluk, Natalie A.; Jones, William M.; Keith, John M.; Krawczuk, Paul; Lebsack, Alec D.; Liu, Jing; Mani, Neelakandha S.; McClure, Kelly J.; Meduna, Steven P.; Rosen, Mark D.; US2015/252008; (2015); 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. 183438-24-6, name is 5-Bromo-2-iodopyrimidine, molecular formula is C4H2BrIN2, 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. Product Details of 183438-24-6

Prepared using General Procedure 10: Into a degassed solution of tert- butyl (S)-2-(5-(tert-butyl)thiophene-2-carboxamido)-3- (4-(4,4,5,5-tetramethyl-l ,3,2- dioxaborolan-2-yl)phenyl)propanoate INT-16 (510 mg, 1.0 mmol) and 5-bromo-2- iodopyrimidine (570 mg, 2.0 mmol) in 2/2/1 ACN/THF/saturated aqueous NaHCO3 (10 mL) was added Pd(dppf)Cl2 (30 mg, 0.4 mmol). The reaction mixture was heated at 120 C for 1 h in a microwave reactor. The reaction mixture was diluted with water (100 mL) and EA (50 mL) and filtered over Celite. The aqueous layer was extracted with EA (3 x 30 mL) and the combined organic layer was dried over MgSO4, concentrated, and purified by chromatography (EA / hexanes) to provide 342 mg (63%) of tert-butyl (S)-3-(4-(5-bromopyrimidin-2-yl)phenyl)-2-(5-( tert-buty)lthiophene-2- carboxamido)propanoate INT-17. LCMS-ESI (m/z) calculated for C26H30BrN3O3S: 543.1 ; found: 488.0 [M-tBu+H]+, tR = 10.95 min (Method 2).

With the rapid development of chemical substances, we look forward to future research findings about 183438-24-6.

Reference:
Patent; RECEPTOS, INC.; BOEHM, Marcus, F.; MARTINBOROUGH, Esther; MOORJANI, Manisha; TAMIYA, Junko; HUANG, Liming; YEAGER, Adam R.; BRAHMACHARY, Enugurthi; FOWLER, Thomas; NOVAK, Andrew; MEGHANI, Premji; KNAGGS, Michael; (204 pag.)WO2016/15014; (2016); A1;,
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Application of 5750-76-5, 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. 5750-76-5, name is 2,4,5-Trichloropyrimidine. A new synthetic method of this compound is introduced below.

Intermediate 2; 2,,5-Dichloro-N-(5-methyl-lH-pyrazol-3-yl)pyrimidin-4-amine To a solution of 5-methyl-lH-pyrazol-3-amine (2.78 g, 27.3 mmol) in absolute EtOH (30 ml) was added triethylamine (5 ml) and 2,4,5-trichloropyrimidine (5.0 g, 27.3 mmol) and the resulting solution was aged at room temperature for 12 hours. The mixture was partitioned between EtOAc and H2O, the organic layer was washed with brine and dried. The solvents were removed under reduced pressure to give the title compound (4.1 g). LC-MS: 245 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,5750-76-5, 2,4,5-Trichloropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/7753; (2009); A2;,
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Pyrimidine – Wikipedia

Application of 10320-42-0, 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. 10320-42-0, name is 2-Chloro-5-nitropyrimidine. A new synthetic method of this compound is introduced below.

(3S)-1o-(3-aminopyrrolidin- 1-yl)-9-fluoro-3-methyl-7-oxo-2,3-dihydro-7H- [1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid (40 mg, 0.115 mmol, 1 eq) was dissolved in dimethyl sulfoxide (2 mL) with 2-Chloro-5-nitropyflmidine (36.74 mg, 0.230 mmol, 2 eq) in a s mL capacity microwave vessel fitted with a magnetic stirrerbar and microwaved at 160¡ãC for 1.5 hours. The DMSO was evaporated the compound was crystalized using hot ethanol to afford compound A1.27. 1H NMR (400 MHz, DMSO-d6) 6 15.38 (br. s., 1H), 9.15 (d, J = 3.30 Hz, 1H), 9.08 (d, J= 3.30 Hz, 1H), 8.90 (s, 1H), 7.56 (d, J = 14.12 Hz, 1H), 4.90-4.85 (m, 1H), 4.60 – 4.56 (m, 1H), 4.53 (d, J = 11.74 Hz, 1H), 4.28 (d, J = 11.19 Hz, 1H), 4.05 ? 3.90 (m, 2H), 3.75 – 3.83-3.68 (m, 2H), 2.22 (tcl, J = 6.53, 12.79 Hz, 1H), 2.05 (dcl, J = 6.51, 12.56 Hz, 1H),1.45 (ci, J = 6.79 Hz, 3H); Formula C21H19FN606 LC-MC Retention time 3.362 mm,Found 471.1 [M+H]

At the same time, in my other blogs, there are other synthetic methods of this type of compound,10320-42-0, 2-Chloro-5-nitropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; KING’S COLLEGE LONDON; THE SECRETARY OF STATE FOR HEALTH; RAHMAN, Khondaker Mirazur; JAMSHIDI, Shirin; LAWS, Mark Benjamin; NAHAR, Kazi; SUTTON, John Mark; HIND, Charlotte; (265 pag.)WO2018/220365; (2018); A1;,
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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. 761440-16-8, name is 2,5-Dichloro-N-(2-(isopropylsulfonyl)phenyl)pyrimidin-4-amine. A new synthetic method of this compound is introduced below., Safety of 2,5-Dichloro-N-(2-(isopropylsulfonyl)phenyl)pyrimidin-4-amine

Isopropanol (445 kg) was added to 2,5-dichloro-N-(2-(isopropylsulfonyl)phenyl)pyrimidin-4-amine (70.2 kg, 203 mol, 1.15 eq.) and 2-Isopropoxy-5-methyl-4-(piperidin-4-yl)aniline dihydrochloride (56.7 kg, 176 mol). The mixture was heated for approx. 16 hours at reflux. Water (47 kg) was added and the mixture cooled to 0 C. The solid was filtered and washed with isopropanol/water. To the wet product, isopropanol (680 kg) and water (55 kg) was added and the slurry heated to reflux. The obtained clear solution was cooled to 0 C., filtered and dried under vacuum to yield 5-chloro-N2-(2-isopropoxy-5-methyl-4-(piperidin-4-yl)phenyl)-N4-(2-(isopropylsulfonyl)phenyl)pyrimidine-2,4-diamine dihydrochloride (=ceritinib dihydrochloride; 84.5 kg [t.q., contains 10% w/w isopropanol], 76.0 kg [100%], 68% yield). Ethanol (155 kg) and water (113 kg) were added to 5-chloro-N2-(2-isopropoxy-5-methyl-4-(piperidin-4-yl)phenyl)-N4-(2-(isopropylsulfonyl)phenyl)pyrimidine-2,4-dihydrochloride; 45.0 kg [t.q., contains 10% w/w isopropanol], 40.5 kg [100%], 64.2 mol) and the mixture heated to 55 C. Aqueous NaOH (147 L of a 1 M solution, 2.3 eq.) was added slowly and then cooled to 20 C. After filtration, the product was recrystallized from ethanol and dried under vacuum to yield ceritinib (33.2 kg, 93% yield based on ceritinib dihydrochloride) as an almost white powder. 1H-NMR (400 MHz, CDCl3): delta=1.33 (d, J=6.8 Hz, 6H), 1.38 (d, J=6.1 Hz, 6H), 1.59-1-78 (m, 5H), 2.18 (s, 3H), 2.75-2.83 (m, 3H), 3.20-3.24 (m, 2H), overlaps 3.28 (sept, J=6.8 Hz, 1H), 4.56 (sept, J=6.1 Hz, 1H), 6.82 (s, 1H), 7.25-7.29 (m, 1H), 7.56 (br. s, 1H), 7.64 (m, 1H), 7.94 (m, 1H), 8.01 (br. s, 1H), 8.16 (br. s, 1H), 8.60 (m, 1H), 9.51 (br. s, 1H) ppm. 13C-NMR (100 MHz, CDCl3): delta=15.4, 18.9, 22.3, 33.9, 38.6, 47.5, 55.4, 71.4, 105.7, 111.0, 120.6, 123.1, 123.7, 124.9, 126.7, 127.3, 131.2, 134.7, 138.3, 138.5, 144.7, 155.3, 155.4, 157.5 ppm, Elemental analysis: calculated (%) for C28H36ClN5O3S: C 60.26, H 6.50, N 12.55, O 8.60 Cl 6.35, S 5.74, found: C 60.15, H 6.45, N 12.72, O 8.58, Cl 6.43, S 5.67.)

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, 761440-16-8, 2,5-Dichloro-N-(2-(isopropylsulfonyl)phenyl)pyrimidin-4-amine.

Reference:
Patent; Novartis AG; Davis, Mark Clinton; Gong, Baoqing; Har, Denis; Kapferer, Tobias; Zheng, Xuchun; (25 pag.)US2020/39935; (2020); A1;,
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Related Products of 16357-69-0, 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.16357-69-0, name is 4-Aminopyrimidine-5-carbonitrile, molecular formula is C5H4N4, molecular weight is 120.11, as common compound, the synthetic route is as follows.

General procedure: Substrate (1.0 mmol), [HDBN+][TFE-] (6.0 mmol) were loaded in a 10 mL glass reaction tube equipped with a magnetic stirrer. The air in the reactor was replaced by CO2. Then, the reactor was stirred at the desired temperature for 3-96 h under CO2 using a balloon. After the reaction, the reaction liquid was cooled to room temperature and quenched by saturated ammonium chloride solution. Then the mixture was filtered to afford the crude product, which was purified by chromatography (silica gel, methanol/dichloromethane=1/20) to give the desired compound. The purified product was characterized by NMR and HR-MS. 1H NMR and 13C NMR studies were carried out with a JEOL NMR 400 (400 MHz, 100 MHz) spectrometer with DMSO-d6 as the solvent. Mass spectra were recorded with an AMD40223(Interambulacra) spectrometer.

The chemical industry reduces the impact on the environment during synthesis 16357-69-0, I believe this compound will play a more active role in future production and life.

Reference:
Article; Li, Chun; Lu, Xunhua; Yang, Yuanyong; Yang, Shenggang; Zhang, Lin; Tetrahedron Letters; vol. 59; 25; (2018); p. 2463 – 2466;,
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Related Products of 7461-50-9, 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 7461-50-9, name is 2-Chloropyrimidin-4-amine. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 3-(5-aminopyrazin-2-yl)-6-cyclobutyl-2-fluorophenol (17.0 g, 65.6 mmol), K2CO3 (13.6 g, 98.4 mmol), 2-chloropyrimidin-4-amine (8.9 g, 69 mmol), 18-crown-6 (0.87 g, 3.3 mmol), and DMA (131 mL) was stirred at 120 Celsius for 15 hours. Water (306 mL) was added, and the reaction mixture cooled to room temperature. Solid precipitate was collected by vacuum filtration and dried in a vacuum oven at 70 Celsius to give the crude product (23.1 g, 100%). The solid was recrystallized from EtOH and treated successively with activated charcoal and silica-supported thiol to remove residual Pd and afford the title compound (13.0 g, 56%). MS (ESI): mass calcd. for C18H17FN6O, 352.14; m/z found, 353.2 [M+H]+. 1H NMR (500 MHz, DMSO-d6) delta 8.25 (s, 1H), 8.01 (d, J=1.5, 1H), 7.83 (d, J=5.8, 1H), 7.66 (m 1H), 7.23 (d, J=8.3, 1H), 7.06 (s, 2H), 6.67 (s, 2H), 6.17 (d, J=5.8, 1H), 3.60-3.47 (m, 1H), 2.19-2.01 (m, 4H), 1.98-1.85 (m, 1H), 1.80-1.68 (m, 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 7461-50-9, 2-Chloropyrimidin-4-amine.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; Eccles, Wendy; Fitzgerald, Anne E.; Hack, Michael D.; Hawryluk, Natalie A.; Jones, William M.; Keith, John M.; Krawczuk, Paul; Lebsack, Alec D.; Liu, Jing; Mani, Neelakandha S.; McClure, Kelly J.; Meduna, Steven P.; Rosen, Mark D.; US2015/252008; (2015); A1;,
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