Tag: M.W:100-200

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. 2927-71-1, name is 2,4-Dichloro-5-fluoropyrimidine. A new synthetic method of this compound is introduced below., Safety of 2,4-Dichloro-5-fluoropyrimidine

To a solution of 2,4-dichloro-5-fluoropyrimidine (1 .02 g, 6.08 mmol) inTHF/NMP (38 mL/3 ml_) was added Fe(acac)3 (215 mg, 0.61 mmol) and the mixture was cooled to 0 oC. 3.0 M methylmagnesium bromide in Et2O (3.04 ml_, 9.12 mmol) was added dropwise. After 30 min at 0 oC, the reaction was complete and quenched with saturated aqueous NH CI solution. Et2O was added and the layers were separated and the aqueous layer was further extracted with several portions of Et2O. The combined organic extracts were dried over Na2SO4, filtered and concentrated in vacuo. Chromatography (Hexanes to 10% EtOAc/Hexanes) gave the desired product as a waxy white solid (430 mg, 48%). 1H NMR (400 MHz, CDCI3): 8.35 (s, 1 H), 2.55 (d, J = 2.5 Hz, 3H).

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, 2927-71-1, 2,4-Dichloro-5-fluoropyrimidine.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; CHAI, Wenying; LETAVIC, Michael, A.; LY, Kiev, S.; PIPPEL, Daniel, J.; RUDOLPH, Dale, A.; SAPPEY, Kathleen, C.; SAVALL, Brad, M.; SHAH, Chandravadan, R.; SHIREMAN, Brock, T.; SOYODE-JOHNSON, Akinola; STOCKING, Emily, M.; SWANSON, Devin, M.; WO2011/50198; (2011); A1;,
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. 22536-66-9, name is 2-Chloropyrimidine-4-carboxamide. A new synthetic method of this compound is introduced below., Product Details of 22536-66-9

2.4. 2-[1-[2-(4-Fluorophenoxy)ethyl]piperidin-4-ylamino]-pyrimidine-4-carboxamide, hydrochloride. 5.5 g (0.02 mol) of 1-[2-(4-fluorophenoxy)ethyl]-piperidin-4-amine, 3.15 g (0.02 mol) of 2-chloropyrimidine-4-carboxamide, 6.91 g (0.05 mol) of potassium carbonate and 0.4 g of sodium iodide are suspended, under argon, in 40 ml of N,N-dimethylformamide. The mixture is stirred at room temperature for 17 hours and then at 40-45 C. for 8 hours. The mixture is cooled to room temperature, poured into 150 ml of water and extracted with ethyl acetate. The organic phase is washed with water, dried over magnesium sulphate, filtered and the solvent evaporated under reduced pressure. After chromatography on silica (eluent: dichloromethane/methanol 97.5/2.5 to 90/10), 4.95 g of base are obtained. The hydrochloride is prepared from it by reaction with a 0.1N hydrochloric acid solution in 2-propanol. After recrystallisation from ethanol, 4.1 g of compound are obtained. Melting point: 202-205 C.

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, 22536-66-9, 2-Chloropyrimidine-4-carboxamide.

Reference:
Patent; Synthelabo; US5246939; (1993); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 696-82-2 ,Some common heterocyclic compound, 696-82-2, molecular formula is C4HF3N2, 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.

(1) 1-Acetyl-4-(4,6-difluoropyrimidin-2-yl)piperazine To a solution of 2,4,6-trifluoropyrimidine (2.0 g) and potassium carbonate (3.1 g) in acetonitrile (15 ml) was added a solution of 1-acetylpiperazine (1.9 g) in acetonitrile (5 ml) over 10 min under ice-cooling and the mixture was stirred at room temperature for 1 hr. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with brine and dried over anhydrous sodium sulfate. The solvent was evaporated to give a pale-yellow oil. The obtained pale-yellow oil was purified by silica gel column chromatography to give the title compound (1.8 g) and 1-acetyl-4-(2,6-difluoropyrimidin-4-yl)piperazine (1.7 g) both as a white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,696-82-2, its application will become more common.

Reference:
Patent; Mitsubishi Pharma Corporation; US6455528; (2002); B1;,
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. 95928-49-7, name is Ethyl 2-hydroxypyrimidine-5-carboxylate, the common compound, a new synthetic route is introduced below. Safety of Ethyl 2-hydroxypyrimidine-5-carboxylate

Step 10d: Ethyl 2-chloropyrimidine-5-carboxylate (Compound 0305)[0216]A mixture of compound 0304 (3.60 g, 21 mmol), phosphorus oxychloride (25 mL), and N,N-dimethylaniline (2.5 mL) was heated at reflux for 1.5 h. After removal of the solvent, ice water (10 mL) was added to the residue. The mixture was added to 2 N NaOH (90 ml), and extracted with EtOAc. The organic layer was evaporated and purified by column chromatography (ethyl acetate in petroleum ether, 5percent v/v) to give compound 0305 (1.20 g, 30percent): LCMS: 187 [M+1]+, 1H NMR (300 MHz, CDCl3): delta 1.42 (t, J=7.5 Hz, 3H), 4.48 (q, J=7.5 Hz, 2H), 9.15 (s, 2H); 1H NMR (400 MHz, DMSO-d6): delta 1.33 (t, J=6.8 Hz, 3H); 4.37 (q, J=6.8 Hz, 2H), 9.18 (s, 2H).

The synthetic route of 95928-49-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Curis, Inc.; Bao, Rudi; Lai, Chengjung; Qian, Changgeng; US2013/102595; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 14080-59-2, 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.14080-59-2, name is 4-Chlorothieno[2,3-d]pyrimidine, molecular formula is C6H3ClN2S, molecular weight is 170.62, as common compound, the synthetic route is as follows.

Examples 308 and 309 Synthesis of 6-bromo-4-chlorothieno[2,3-d]pyrimidine and 6-bromo-2-butyl-4-chlorothieno[2,3-d]pyrimidine n-BuLi (1.6 M in hexane, 1.9 ml, 2.5 mmol) in THF (8 ml) was cooled to -78 C. 4-Chlorothieno[2,3-d]pyrimidine (0.34 g, 2.0 mmol) was dissolved in THF (2 ml) and slowly added to the reaction mixture over 5 minutes. After 20 min, CBr4 (0.73 g, 2.2 mmol) in THF (3 ml) was slowly added to the reaction mixture. The temperature was maintained at -78 C. for 20 minutes and then warmed to room temperature for 2 hours. The mixture was poured into water and extracted with chloroform, dried over sodium sulfate, and concentrated in vacuo. The crude residue was purified by silica gel chromatography (EtOAc/hexane 40:1) to yield two pure compounds a white solid (example 203: 0.13 g, 25% and example 204: 0.16 g, 26%).

The chemical industry reduces the impact on the environment during synthesis 14080-59-2, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Katholieke Universiteit Leuven, K.U. Leuven R&D; Herman, Jean; Louat, Thierry; US2014/88088; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 5305-59-9, Adding some certain compound to certain chemical reactions, such as: 5305-59-9, name is 6-Chloropyrimidin-4-amine,molecular formula is C4H4ClN3, 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 5305-59-9.

A mixture of 4-(4-bromothiazolo[5,4-c]pyridin-2-yl)-3,5-dichlorobenzonitrile (0.250 g, 0.65 mmol), 4-amino-6-chloropyridine (0.080 g, 0.62 mmol), Pd2(dba)3 (0.030 g, 0.033 mmol), XantPhos (0.038 g, 0.065 mmol) and cesium carbonate (0.530 g, 1.60 mmol) in dioxane (6.5 mL) was degassed with nitrogen then heated at 70 C for 4 hours. The resulting mixture was diluted with DCM and water, and then filtered through Celite. The layers of the filtrate were separated and the organic layer, dried over Na2S04 and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography eluting with 0- 25% EtOAc in pentane and 0-10% EtOAc in DCM to give the desired compound as a yellow solid (0.215 g, 76% yield). ¾ NMR (300 MHz, DMSO-t¾: delta 11.16 (s, 1H), 8.65 (s, 1H), 8.52 (d, J= 5.6 Hz, 1H), 8.39 (s, 2H), 7.97 (s, 1H), 7.91 (d, J= 5.6 Hz, 1H). LCMS (Method E): RT = 3.83 min, m/z: 433 [M+H+].

According to the analysis of related databases, 5305-59-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BLENCH, Toby; ELLWOOD, Charles; GOODACRE, Simon; LAI, Yingjie; LIANG, Jun; MACLEOD, Calum; MAGNUSON, Steven; TSUI, Vickie; WILLIAMS, Karen; ZHANG, Birong; WO2012/35039; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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.5399-92-8, name is 4-Chloro-1H-pyrazolo[3,4-d]pyrimidine, molecular formula is C5H3ClN4, molecular weight is 154.5571, as common compound, the synthetic route is as follows.Computed Properties of C5H3ClN4

Example 2 Preparation of 4-(1H-pyrazolo-4-phenoxy)aniline (3a-1) P-aminophenol (0.55g, 5.5mmol) and sodium hydroxide (0.20g, 5.5mmol) were added to 10mL water; potassium carbonate (0.76g, 5.5mmol) was added after resulting mixture was stirred for 30 minutes at normal temperature; the temperature was increased to 60C, and tetrahydrofuran solution of 4-chloro-1H-pyrazolopyrimidine (intermediate 2) (0.94g, 6.6mmol) was slowly added to the reaction solution; after one hour, reaction was stopped; after the tetrahydrofuran of the reaction system was distilled to dryness, the remaining system was extracted with ethyl acetate and water twice; the ethyl acetate layer was dried with anhydrous magnesium sulfate and then spun dry, and then introduced into a column for purification to obtain 0.77g 4-(1H-pyrazolo-4-phenoxy)aniline (3a-1) at a yield of 62.1%. 1H NMR (400 MHz, DMSO-d6): delta 14.07(s, 1H), 8.50(s, 1H), 7.67(s, 1H), 6.96(d, J=8.8 Hz, 2H), 6.64(d, J=8.8 Hz, 2H), 5.20(s, 2H) ppm. LCMS m/z: 228.1 [M + H].

At the same time, in my other blogs, there are other synthetic methods of this type of compound,5399-92-8, 4-Chloro-1H-pyrazolo[3,4-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; GUANGXI WUZHOU PHARMACEUTICALS (GROUP) CO., LTD.; YANG, Shengyong; WEI, Yuquan; EP2889298; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 91717-22-5, Adding some certain compound to certain chemical reactions, such as: 91717-22-5, name is 2-Amino-4-piperidino-6-methylpyrimidine,molecular formula is C10H16N4, 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 91717-22-5.

In a 100 mL jar, 2-amino-4-piperidinyl-6-methylpyrimidine (0.001 mol) was added,P-tolualdehyde (0.001 mol) and dimethyl malonate (0.0015 mol) were added with p-xylene (30 mL) as a solvent. The reaction was terminated in microwave at 100C for 50 minutes, and paraxylene was recovered under reduced pressure.Column chromatography (petroleum ether:ethyl acetate=4:1 V/V) gave the desired product.

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. 91717-22-5, 2-Amino-4-piperidino-6-methylpyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Guizhou Institute Of Technology; Bai Song; Zhu Yunying; Wei Xian; Wu Qin; Zou Shuliang; Tang Qin; Gong Zhihai; Zhou Han; Zhou Hang; (14 pag.)CN108101855; (2018); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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.76196-80-0, name is Methyl 5-methylpyrimidine-2-carboxylate, molecular formula is C7H8N2O2, molecular weight is 152.1506, as common compound, the synthetic route is as follows.Application In Synthesis of Methyl 5-methylpyrimidine-2-carboxylate

To a solution of 211 methyl 5-methylpyrimidine-2-carboxylate [Example 9, Step 2] (2.5 g, 16.4 mmol, 1.00 equiv) in 89 methanol (40 mL) was added 212 NaBH4 (1.87 g, 49.3 mmol, 3.00 equiv) at 0 C. The resulting solution was stirred for 3 h at 25 C. The reaction was then quenched by the addition of 24 H2O (40 mL). The resulting mixture was concentrated under vacuum to remove MeOH. The resulting solution was extracted with ethyl acetate (3×50 mL). The organic layers were dried over anhydrous sodium sulfate and concentrated under vacuum to afford 1.3 g (63.9%) of 189 (5-methylpyrimidin-2-yl)methanol as a yellow solid. LC-MS: m/z=125 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,76196-80-0, Methyl 5-methylpyrimidine-2-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Auspex Pharmaceuticals, Inc.; ZHANG, Chengzhi; (94 pag.)US2018/79742; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 69034-12-4, 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. 69034-12-4, name is 2-Chloro-5-(trifluoromethyl)pyrimidine. A new synthetic method of this compound is introduced below.

A mixture of (R)-5-(1-methanesulfonyl-1,2,3,6-tetrahydro-pyridin-4-yl)-2-piperidin-4-yl-2,3-dihydro-furo[2,3-c]pyridine (Intermediate 39, the configuration of the stereocenter is arbitrarily assigned; 110 mg}, 2-chloro-5-trifluoromethyl-pyrimidine (76 mg), K2CO3 (100 mg), and dimethyl sulfoxide (1.5 mL) is stirred at 110 C. for 3 h. After cooling to room temperature, water is added and the resulting mixture is extracted with ethyl acetate. The combined extracts are washed with brine, dried (Na2SO4), and concentrated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 30:70?10:90) to give the title compound. LC (method 5): tR=1.32 min; Mass spectrum (ESI+): m/z=510 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,69034-12-4, 2-Chloro-5-(trifluoromethyl)pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HIMMELSBACH, Frank; LANGKOPF, Elke; NOSSE, Bernd; US2013/18030; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia