Month: April 2021

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. 62802-42-0, name is 2-Chloro-5-fluoropyrimidine. A new synthetic method of this compound is introduced below., category: pyrimidines

Under nitrogen, a solution of sodium carbonate (4.24g, 40 mmol) in water (20 mL) was added to asolution of 2-chloro-5-fluoropyrimidine 4 (2.47 mL, 20 mmol) in toluene (60 mL), and the mixture washeated to 80 C. Bis(triphenylphosphine)palladium(II) chloride (701.9 mg, 1 mmol) was added, and asolution of 3-(hydroxymethyl)phenylboronic acid (3.34 g, 22 mmol) in ethanol (20 mL) wassubsequently added dropwise. The reaction mixture was stirred at 90 C for 12 hours. The reactionmixture was cooled to room temperature and filtered. The aqueous phase was extracted with AcOEt(100 mL x 3). The combined organic layer was washed with H2O (30 mL) and brine (20 mL), and thendried over anhydrous Na2SO4, filtered and evaporated in vacuo. The residue was purified by flashchromatography over silica gel (petroleum/EtOAc = 10:13:1) to give(3-(5-fluoropyrimidin-2-yl)phenyl)methanol 5 (68%).

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, 62802-42-0, 2-Chloro-5-fluoropyrimidine.

Reference:
Article; Zhang, Niu-niu; An, Bai-jiao; Zhou, Yan; Li, Xing-shu; Yan, Ming; Molecules; vol. 24; 6; (2019);,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 5604-46-6, 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. 5604-46-6, name is 2-Amino-4,6-dichloropyrimidine-5-carbaldehyde, molecular formula is C5H3Cl2N3O, 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.

4-(4-methoxyphenyl)aniline under nitrogen protection(11.4 g, 57.3 mmol, which can be synthesized by reference to RazlerTM et al. Journal of Organic Chemistry; vol. 74; nb. 3; (2009); p. 1381-1384)The anhydrous tetrahydrofuran (120 mL) solution was cooled with an ice water bath.Sodium hydrogen (60% mineral oil powder, 4.6 g 114.6 mmol) was carefully added in portions.After the addition was completed, the reaction was further stirred for about half an hour, and 2-amino-4,6-dichloropyrimidine-5-carbaldehyde (10.0 g, 52.1 mmol) was further added.The ice water bath was removed, and the reaction was allowed to react at room temperature for about 8-10 hours, and was monitored by TLC (petrole ether: ethyl acetate = 2:1) until the reaction was completed.The reaction was quenched by dropwise addition of water (20 mL). Additional ethyl acetate (200 mL) was added. The resulting mixed solution was washed with saturated brine (100 mL*3).The organic layer was dried over anhydrous sodium sulfate, filtered, evaporated, evaporated, evaporated, evaporated. 2-amino-4-(4-(4-methoxyphenyl)anilino)-6-chloropyrimidine-5-carboxaldehyde in a yield of 82.7%.

According to the analysis of related databases, 5604-46-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chengdu University of Technology; Zhou Lihong; (40 pag.)CN105111151; (2018); B;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route 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.

The first step: a vacuum 50mL reaction bottle is vacuumed three times,After adding o-toluidine (107 mg, 1.0 mmol, 1.0 equiv) to the reaction jar,Add 10.0 mL of dried acetonitrile and stir until the aniline is completely dissolved.Then 2-chloro-5-nitropyrimidine (0.1593 g, 1.0 mmol, 1.0 equiv) was added to the reaction flask.The entire mixture was reacted under nitrogen pressure for 5 hours.The reaction detects the progress of the reaction by TLC.The reaction can be stopped if it is detected that all the aniline is completely reacted.The experimental treatment is to drain the solution in the reaction;The solute in the reaction flask was dissolved with ethyl acetate.And transferred to a 100 mL round bottom flask,2 mL (200-300 mesh) of silica gel was added to a round bottom flask for spin-drying (petroleum ether and ethyl acetate) over silica gel.Wait until the intermediate product is pale yellow crystal5-nitro-N-(o-tolyl)pyrimidin-2-amine(207 mg, 90% yield)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,10320-42-0, its application will become more common.

Reference:
Patent; Jinan University; Feng Pengju; Chen Tianfeng; Chen Junfeng; Huang Yifeng; (25 pag.)CN108148005; (2018); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 2915-16-4 ,Some common heterocyclic compound, 2915-16-4, molecular formula is C16H11ClN2, 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.

NaH (1.9 mg, 42.1 mmol) was dissolved in dimethylformamide (DMF) in a flask and the mixture was stirred. Compound 5-2 (7.0 g, 27.2 mmol) was dissolved in DMF in a flask and added to the stirred NaH solution, and the mixture was stirred for 1 hr. 2-Chloro-4,6-diphenylpyrimidine (8.7 g, 32.6 mmol) was dissolved in DMF in a flask and stirred. The mixture stirred for 1 hr was added thereto and then stirred at room temperature for 24 hrs. After completing the reaction, the resulting solid was filtered, washed with EA, and purified by column chromatography to obtain compound H-33 (3.5 g, 25 %).

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. 2915-16-4, 2-Chloro-4,6-diphenylpyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ROHMANDHAASELECTRONICMATERIALSKOREA LTD; LEE, KYUNG-JOO; YOON, SEOK-KEUN; KIM, CHI-SIK; KIM, HYUN; LEE, SEON-WOO; JUNG, SO-YOUNG; LEE, SU-HYUN; YANG, JEONG-EUN; KIM, YOUNG-KWANG; CHO, YOUNG-JUN; PARK, KYOUNG-JIN; JANG, SUNG-WOO; (50 pag.)TW2016/5841; (2016); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 56621-89-7, 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.56621-89-7, name is 5-Amino-2-methoxypyrimidine, molecular formula is C5H7N3O, molecular weight is 125.1286, as common compound, the synthetic route is as follows.

Step 1. l-(4-Bromophenyl)-N-(2-methoxypyrimidin-5-yl)cyclobutane-l- carboxamide: Into a 200 mL round bottom flask equipped with a magnetic stir bar and under N2 was added 2-methoxypyrimidin-5-amine (1.23 g, 9.80 mmol) and l-(4-bromophenyl)cyclo- butanecarboxylic acid (2 g, 7.84 mmol). The solids were dissolved in EtOAc (20 mL) and treated with pyridine (1.24 g, 15.68 mmol, 1.27 mL) followed by propylphosphonic anhydride (7.48 g, 1 1.76 mmol, 6.99 mL, 50% purity) in EtOAc. The yellow-orange solution was stirred at 24 C for 5 hr, the reaction was worked up by adding HC1 ( 1M, 20 mL). The EtOAc layer was concentrated and purified by column chromatography eluting with 10% to 100 % (0296) EtOAc/hexanes gradient over 10 min. The desired fractions were combined, concentrated and further dried under high vacuum O/N, yielding a white solid (2 g). LCMS (ESI+) m/z = 362,364 (M+l, M+3).

The chemical industry reduces the impact on the environment during synthesis 56621-89-7, I believe this compound will play a more active role in future production and life.

Reference:
Patent; TEMPEST THERAPEUTICS, INC.; POWELL, David Andrew; ROPPE, Jeffrey Roger; SEIDERS, Thomas Jon; DING, Jinyue; SHENG, Tao; JACINTHO, Jason Duarte; (65 pag.)WO2019/79614; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 37131-89-8, 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. 37131-89-8, name is 2,4-Dichloropyrimidine-5-carboxylic acid. A new synthetic method of this compound is introduced below.

To a 50 ml three-necked flask was added successively the crude product (0.6 g, 3.1 mmol) in the previous step,Thionyl chloride (10 ml) and heated to 80 C for 4 hours.Concentrated to dryness under reduced pressure to give 0.6 g of 2,4-dichloro-5-pyrimidinecarboxylic acid chloride in a yield of 90%

At the same time, in my other blogs, there are other synthetic methods of this type of compound,37131-89-8, 2,4-Dichloropyrimidine-5-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; SUZHOU WANGSHAN WANGSHUI BIOMEDICAL CO LTD; TOPHARMAN SHANGHAI CO LTD; SHANDONG TOPHARMAN PHARMACEUTICAL CO LTD; TIAN, GUANGHUI; LI, JUNQI; (17 pag.)CN104650045; (2017); B;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 144927-57-1, 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 144927-57-1, name is Ethyl 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate. This compound has unique chemical properties. The synthetic route is as follows.

To a stirred mixture of ethyl 4-chloro-7H-pyrrolo[2,3-ii|pyrimidine-5-carboxylate (4.00 g, 17.7 mmol) and SEMC1 (4.71 mL, 26.6 mmol) in DMF (90 mL) was added sodium hydride (0.851 g, 21.3 mmol) portion-wise at 0 C. The resulting yellow suspension was stirred at 0 C for one hour and then allowed to warm to room temperature over one hour. The reaction was quenched with water slowly then extracted with ethyl acetate (x3). The combined organic layers were washed with brine (150 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on silica eluting with 0-50% ethyl acetate/hexane to afford ethyl-4-chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo [2,3 –Patent; MERCK SHARP & DOHME CORP.; AHEARN, Sean, P.; CHRISTOPHER, Matthew; JUNG, Joon; PU, Qinglin; RIVKIN, Alexey; SCOTT, Mark, E.; WITTER, David, J.; WOO, Hyun Chong; CASH, Brandon; DINSMORE, Christopher; GUERIN, David; WO2013/85802; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 13036-57-2 , The common heterocyclic compound, 13036-57-2, name is 2-Chloro-4-methylpyrimidine, 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.

To a solution of ethyl 3-{[(2,6-diotafluorophenyl)sulfonyl]amiotano}-4-fluorobenzoate (5 0 g, 13 9 mmol) in THF (100 mL) was added 1 0 M LHMDS in THF (34 8 mL, 34 8 mmol) A solution of 2-chloro-4-methylpyriotamiotadiotane (2 7 g, 20 9 mmol) in THF (100 mL) was added dropwise over 30 mm, and the reaction was stirred overnight at rt The reaction was quenched with 10 mL of MeOH and concentrated, and the residue was partitioned between EtOAc and saturated aqueous sodium bicarbonate The aqueous layer was extracted with 2×50 mL EtOAc, and the combined organic layers were passed through a pad of silica gel, concentrated, and adsorbed onto silica gel The crude product was purified via flash chromatography with 0-100% EtOAc/DCM to generate 3 07 g (50% yield) of the product of Step B as a white powder ES- LCMS m/z 443 (M+H)

The synthetic route of 13036-57-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE LLC; ADJABENG, George; BAUM, Erich; BIFULCO, Neil; DAVIS-WARD, Ronda, G.; DICKERSON, Scott, Howard; DONALDSON, Kelly, Horne; HORNBERGER, Keith; PETROV, Kimberly; RHEAULT, Tara, Renae; SAMMOND, Douglas, McCord; SCHAAF, Gregory, M.; STELLWAGEN, John; UEHLING, David, Edward; WATERSON, Alex, Gregory; WO2010/104899; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 761440-16-8, 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 761440-16-8, name is 2,5-Dichloro-N-(2-(isopropylsulfonyl)phenyl)pyrimidin-4-amine. This compound has unique chemical properties. The synthetic route is as follows.

4-(4-Amino-5-isopropoxy-2-methyl-phenyl)-piperidine-l-carboxylic acid tert-butyl ester (170 mg, 0.488 mmol) from the previous step, (2,5-Dichloro-pyrimidin-4-yl)-[2-(propane- 2-sulfonyl)-phenyl]-amine (Intermediate 2, 169 mg, 0.488 mmol, 1 equiv.), xantphos (28 mg, 0.049 mmol, 0.1 equiv.), palladium acetate (5.5 mg, 0.024 mmol, 0.05 equiv.), and Cs2CO3 (477 mg, 1.46 mmol, 3 equiv.) are dissolved in anhydrous THF (6 mL). N2 is bubbled through the reaction mixture for 5 minutes and then the reaction vessel is sealed and heated with microwave irradiation to 150 0C for 20 min. The reaction is filtered and the filtrate concentrated under vacuum. After concentration, the crude product is purified by silica gel chromatography (gradient from hexanes to 30% ethyl acetate in hexanes) to give 4-(4-{5-chloro-4-[2-(propane-2- sulfonyl)-phenylamino]-pyrimidin-2-ylamino}-5-isopropoxy-2-methyl-phenyl)-piperidine-l- carboxylic acid tert-butyl ester as a yellow film: ESMS m/z 658.3 (M + H+). This product (105 mg, 0.160 mmol) is dissolved in CH2Cl2 (3 mL) and treated with TFA (3 mL). After 45 min., the reaction is concentrated under vacuum. 1 N HCl in Et2O (5 mL x 2) is added causing the product HCl salt to precipitate. The solvent is removed by decantation. The resulting 5- Chloro-N2-(2-isopropoxy-5-methyl-4-piperidin-4-yl-phenyl)-N4-[2-(propane-2-sulfonyl)- phenyl]-pyrimidine-2,4-diamine (66) is dried under high vacuum, generating an off-white powder: 1H NMR (400 MHz, DMSO-J6 + trace D2O) delta 8.32 (s, IH), 8.27 (d, IH), 7.88 (d, IH), 7.67 (dd, IH), 7.45 (dd, IH), 7.42 (s, IH), 6.79 (s, IH), 4.56-4.48 (m, IH), 3.49-3.32 (m, 3H), 3.10-2.91 (m, 3H), 2.09 (s, 3H), 1.89-1.77 (m, 4H), 1.22 (d, 6H), 1.13 (d, 6H); ESMS m/z 558.1 (M + H+).

According to the analysis of related databases, 761440-16-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; IRM LLC; WO2008/73687; (2008); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 33097-13-1 ,Some common heterocyclic compound, 33097-13-1, molecular formula is C6H3Cl2N3S, 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.

(S)-1-(1-Methyl-6-(1-methyl-1H-pyrazol-5-yl)-1H-pyrrolo[3,2-b]pyridin-5-yl)ethanamine 2,2,2-trifluoroacetate (1562 mg, 4.23 mmol) in THF (27.5 mL) along with 4,6- dichloro-2-(methylthio)pyrimidine-5-carbonitrile (931 mg, 4.23 mmol) and Et3N (1297 mu, 9.31 mmol) were added to a pear-shaped flask. The resulting mixture was stirred at room temperature for 2 hours and then concentrated to give the title compound, which was used in next step without further purification. ESI-MS m/z [M+H]+ calc’d for C20H19ClN8S, 439.11; found 439.4.

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. 33097-13-1, 4,6-Dichloro-2-(methylthio)pyrimidine-5-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; CHANG, Edcon; NOTZ, Wolfgang Reinhard Ludwig; WALLACE, Michael B.; WO2014/11568; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia