Day: September 10, 2021

Synthetic Route of 39906-04-2, 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. 39906-04-2, name is 4,6-Dichloro-2-methylpyrimidin-5-amine, molecular formula is C5H5Cl2N3, 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.

General procedure: A microwave vial was charged with 3′-aminoacetanilide 29 (300 mg, 2.0 mmol), 5-amino-4,6-dichloropyrimidine (10) (328 mg, 2.0 mmol), acetic acid (100 muL) and isobutanol (10 mL) and was irradiated at 150 C for 30 min. After cooling, dichloromethane was added (20 mL) and the crude reaction mixture was washed with saturated aqueous NaHCO3 (20 mL). The organic layer was dried over Na2SO4, filtered and evaporated to dryness. The residue was purified by flash chromatography (dichloromethane:methanol).Yield: 300 mg (54%).

According to the analysis of related databases, 39906-04-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Aguado, Leire; Canela, Maria-Dolores; Thibaut, Hendrik Jan; Priego, Eva-Maria; Camarasa, Maria-Jose; Leyssen, Pieter; Neyts, Johan; Perez-Perez, Maria-Jesus; European Journal of Medicinal Chemistry; vol. 49; (2012); p. 279 – 288;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 2972-52-3, 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. 2972-52-3, name is 2,4-Dichloro-5-pyrimidinecarbonyl chloride, molecular formula is C5HCl3N2O, 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.

Ethyl 2,8,9J0J7J9.22-heptaazatricvclori6.3.1. .l0ltricosa-l(2U (23 8 8(22I19- entaene-21 -carboxylate (1279) (1280) A solution of 2,4-dicMoropyrirnidine-5-carbonyl chloride (1.00 g, 4.76 mmol) in ethanol (6.0 mL) was added DIPEA (2.5 mL, 14.4 mmol) slowly at 0 C under nitrogen. After 30 min, hex-5-yn-l -amine (0.476 g, 4.91 mmol) was added in one portion. The reaction mixture was stirred at room temperature for 3.5 h, then was added drop wise to a solution of 6-azidohexan-l -amine (0.801 g, 5.64 mmol) in ethanol (4.0 mL) at 50 C. After the reaction was complete (monitored by LCMS), the mixture was diluted with water (10 mL) and concentrated under a reduced pressure and filtered. The yellow solid was washed with water and dried under vacuum to be used in the next step without further purification (0.723 g, 39% over 3 steps).

According to the analysis of related databases, 2972-52-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THE UNIVERSITY OF NORTH CAROLINA AT CHAPEL HILL; WANG, Xiaodong; ZHANG, Weihe; FRYE, Stephen; WO2015/157127; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 776-53-4 ,Some common heterocyclic compound, 776-53-4, molecular formula is C8H11N3O2S, 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.

Example 12 (4-Amino-2-methanesulfanyl-pyrimidin-5-yl)-methanol A solution of 4-amino-2-methanesulfanyl-pyrimidine-5-carboxylic acid ethyl ester (13.36 g, 63 mmol) in 250 mL of tetrahydrofuran was added dropwise to a room temperature suspension of lithium aluminum hydride (3.82 g, 100 mmol) in 250 mL of tetrahydrofuran. After 30 minutes, the reaction was cooled to 0 C., and isopropyl alcohol was added until bubbling diminished. The reaction was quenched with 15 mL of water, 15 mL of 15% NaOH, and 50 mL of water, and the mixture was stirred for 1 hour. The white precipitate was removed by filtration, washing with ethyl acetate. The filtrate was concentrated in vacuo and 3:1 hexane:ethyl acetate was added. The solids were collected, washed with 3:1 hexane:ethyl acetate, followed by hexane. The solid was dissolved in ethyl acetate, and the solution was dried over magnesium sulfate. Filtration followed by concentration in vacuo gave 8.14 g (76%) of (4-amino-2-methanesulfanyl-pyrimidin-5-yl)-methanol. Analysis calculated for C6H9N3OS: C, 42.09; H, 5.30; N, 24.54. Found: C, 42.31; H, 5.24; N, 24.27.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,776-53-4, its application will become more common.

Reference:
Patent; Booth, Richard John; Chatterjee, Arindam; Malone, Thomas Charles; US2004/224958; (2004); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 720-01-4, 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 720-01-4, name is Ethyl 4-chloro-2-trifluoromethylpyrimidine-5-carboxylate. This compound has unique chemical properties. The synthetic route is as follows.

To a mixture of ethyl 4-chloro-2-(trifluoromethyl)pyrimidine-5-carboxylate (1 g, 3.93mmol) and N,N-diisopropylethylamine (1.37mL, 7.87mmol) in 2-propanol (8 mL) was added morpholine (0.42 mL, 4.92 mmol). The mixture was stirred at room temperature for 3 h and was then concentrated in vacuo. The resulting residue was purified by column chromatography (40% EA/Hex) to give ethyl 2-(trifluoromethyl)-4-moropholinopyrimidine-5-carboxylate as a white solid (1.2g, 98%).1H NMR (DMSO-d6, 400MHz): 8.71(1H, s), 4.32(2H, q), 3.68(4H, t), 3.59(4H, t), 1.31(3H, t). ESI-MS: 306 (M+1)

According to the analysis of related databases, 720-01-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Purushothaman, Baskaran; Arumugam, Parthasarathy; Kulsi, Goutam; Song, Joon Myong; European Journal of Medicinal Chemistry; vol. 145; (2018); p. 673 – 690;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 18740-39-1, name is 2,4-Dichlorothieno[2,3-d]pyrimidine, the common compound, a new synthetic route is introduced below. Recommanded Product: 18740-39-1

General procedure: Weigh 2,4-dichloro-7H-pyrrolopyrimidine (372 mg, 1 eq),P-trifluoromethoxyphenylboronic acid (1000 mg, 1.1 eq), triethylamine (1.2 eq),Bis(triphenylphosphine)palladium(II) chloride (0.1eq), N,N-dimethylformamide(28.5 ml), water (0.5 ml) was added to the flask and the temperature was raised to 85°C for 4 hours.After stopping the reaction, add water to the reaction solution100ml, stirring, ethyl acetate (20ml*4) extraction,The ester layer was dried over anhydrous sodium sulfate, concentrated, and separated by column chromatography.(petroleum ether:ethyl acetate=20:1)Obtained solid (680 mg, 41percent)

The synthetic route of 18740-39-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiangsu Xiansheng Pharmaceutical Co., Ltd.; Xin Minxing; Tang Feng; Wen Jun; Shen Han; Tu Chongxing; Zhao Xinge; (48 pag.)CN104177363; (2018); B;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 69034-12-4, Adding some certain compound to certain chemical reactions, such as: 69034-12-4, name is 2-Chloro-5-(trifluoromethyl)pyrimidine,molecular formula is C5H2ClF3N2, 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 69034-12-4.

Example 1.37: Preparation of 4-((lr,4r)-4-((l-(5-(Trifluoromethyl)pyrimidin-2-yl)piperidin- 4-yl)methoxy)cyclohexyl)nicotinonitrile (Compound 59).; A mixture of 4-((lr,4r)-4-(piperidin-4-ylmethoxy)cyclohexyl)nicotinonitriledihydrochloride (27 mg, 72.52 muetaiotaomicron), 2-chloro-5-(trifluoromethyl)pyrimidine (0.03 ml, 0.164 mmol), and potassium carbonate (50 mg, 0.362 mmol) in 1 ml iPrOH was heated under micorwave irradiation at 85C for 2 h. Mixture was purified by HPLC (CH3CN/H20 gradient + 0.1% TFA). Fractions containing desired product were partly concentrated and residue was extracted with 1 M NaOH and CH2C12. Organic phases were dried over MgS04, filtered, and concentrated to give 4-((lr,4r)-4-((l-(5-(trifluoromethyl)pyrimidin-2-yl)piperidin-4- yl)methoxy)cyclohexyl)nicotinonitrile (14.6 mg, 32.77 muetaiotaomicron, 45.2 %) as a white solid. Exact mass calculated for C23H26F3N50: 445.21, found: LCMS m/z = 446.4 (M+H+); lU NMR (400 MHz, CDC13) delta ppm 1.17-1.28 (m, 2H), 1.41-1.62 (m, 4H), 1.85-2.04 (m, 5H), 2.18-2.24 (m, 2H), 2.90-2.99 (m, 3H), 3.26-3.33 (m, 1H), 3.38 (d, = 6.0 Hz, 2H), 4.84-4.90 (m, 2H), 7.28 (d, = 5.3 Hz, 1H), 8.47 (s, 2H), 8.80 (d, = 5.3 Hz, 1H), 8.81 (s, 1H).

According to the analysis of related databases, 69034-12-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; JONES, Robert M.; HAN, Sangdon; LEHMANN, Juerg; THORESEN, Lars; WO2012/135570; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 4316-93-2, 4,6-Dichloro-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, category: pyrimidines, blongs to pyrimidines compound. category: pyrimidines

To amino-acetic acid ethyl ester hydrochloride (1439.15 mg; 10.31 mmol; 1 .00 eq.) and 4,6-Dichloro-5-nitro-pyrimidine (2000.00 mg; 10.31 mmol; 1 .00 eq.) in dry DMF (26 mL) was added ethyl-diisopropyl-amine (3997.72 mg; 30.93 mmol; 3.00 eq.) and the mixture was stirred for 3 hours. LC-MS showed that the reaction was complete. The DMF was removed and the EtOAc was added.The mixture was washed with brine, dried over MgS04 and purified through flash chromatography on silica (EtOAc in Hexane from 0% to 30%) to provide (6-chloro-5-nitro-pyrimidin-4-ylamino)-acetic acid ethyl ester 2.1 g with 78% yield; LC/MS: 261 (M+H)

The synthetic route of 4316-93-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK PATENT GMBH; LAN, Ruoxi; HUCK, Bayard R.; CHEN, Xiaoling; XIAO, Yufang; WO2014/78637; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 37131-87-6, 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.37131-87-6, name is 5-Bromopyrimidine-2-carboxylic acid, molecular formula is C5H3BrN2O2, molecular weight is 202.99, as common compound, the synthetic route is as follows.

To a solution of 5-bromopyrimidine-2-carboxylic acid (3.22 g, 15.9 mmol) in MeOH (50 mL) at room temperature was added acetyl chloride (4.0 mL, 56.3 mmol). The reaction mixture was heated to reflux for 15 min, cooled to room temperature and concentrated under reduced pressure. The reaction mixture was diluted with saturated NaHCO3 (30 mL) and EtOAc, and transferred to a separatory funnel. The aqueous phase was extracted with EtOAc (4 x) and the combined organic extracts were washed with brine (1 x), dried over MgSO4, filtered, and concentrated to give methyl 5- bromopyrimidine-2-carboxylate (2.30 g, 10.6 mmol, 67% yield) as a white solid. LC/MS (ESI+) m/z = 216.9 (M+H). Calculated for C6H5BrN2O2216.0

The chemical industry reduces the impact on the environment during synthesis 37131-87-6, I believe this compound will play a more active role in future production and life.

Reference:
Patent; AMGEN INC.; ALLEN, Jennifer R.; AMEGADZIE, Albert; BOURBEAU, Matthew P.; BROWN, James A.; CHEN, Jian J.; CHENG, Yuan; FROHN, Michael J.; GUZMAN-PEREZ, Angel; HARRINGTON, Paul E.; LIU, Longbin; LIU, Qingyian; LOW, Jonathan D.; MA, Vu Van; MANNING, James; MINATTI, Ana Elena; NGUYEN, Thomas T.; NISHMURA, Nobuko; NORMAN, Mark H.; PETTUS, Liping H.; PICKRELL, Alexander J.; QIAN, Wenyuan; RUMFELT, Shannon; RZASA, Robert M.; SIEGMUND, Aaron C.; STEC, Markian M.; WHITE, Ryan; XUE, Qiufen; (759 pag.)WO2016/22724; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 5018-38-2, 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 5018-38-2 as follows.

4-(5-Methoxy-4-pyrimidinyl)-2-methylpiperazine Method 2 A solution of 2-methylpiperazine (20 g) in water (100 mL) was reacted with solid 4,6-dichloro-5-methoxypyrimidine (5.00 g, 27.9 mmole) in a procedure similar to that given for Method 2 of Example 14. After hydrogenation and filtration of the catalyst, the product was extracted from the filtrate with CH2 Cl2. The extracts were concentrated in vacuo, and the residue was Kugelrohr distilled to give a clear oil (5.46 g, 99.8%). The oil was dissolved in acetonitrile and concentrated HCl added to form the salt which was recrystallized from i-PrOH and dried in vacuo to give the product as a white powder (4.02 g, m.p. 185-188 C.).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5018-38-2, its application will become more common.

Reference:
Patent; Bristol-Myers Squibb Company; US5434154; (1995); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 3764-01-0 ,Some common heterocyclic compound, 3764-01-0, molecular formula is C4HCl3N2, 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 2-liter, 3-neck flask equipped with mechanical stirrer, thermometer and dropping funnel was loaded with ethanol (375 mL), water (375 mL) and morpholine, (1.01 mol, 88 g); the resulting solution was cooled (with sodium chloride- ice mixture) to about 0 0C and a solution of 2,4,6-trichloropyrimidine (91.17 g, 0.5 mol) in ethyl acetate (37.5 mL) was added dropwise in about 20 minutes, to maintain temperature below 10 0C. The dropping funnel was rinsed twice with ethyl acetate (3 mL), and the rinses were transferred to the reaction mixture. The reaction was checked by TLC to determine when the reaction was complete. After completion of the reaction, ice water (375 mL) was added, and reaction was allowed to stir for 30 minutes to complete precipitation. The colorless solid was filtered out, washed 6 times with water (225 mL per wash) and vacuum-dried at 40-50 0C until a constant weight of the product was maintained. The product (114.7 g, 98% yield) was a mixture of regioisomers 6-morpholino-2,4- dichloropyrimidine and 2-morpholino-4,6-dichloropyrimidine in about a 3.9:1 ratio which were separated by chromatograph to 6-morpholino-2,4-dichloropyrimidine.

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. 3764-01-0, 2,4,6-Trichloropyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SYNTA PHARMACEUTICALS CORP.; WO2006/124662; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia