Day: March 10, 2021

Application of 29274-24-6 ,Some common heterocyclic compound, 29274-24-6, molecular formula is C6H4ClN3, 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.

Preparation 8; 5-Chloropyrazolo [1, 5-a] pyrimidine (100 mg) andN-iodosuccinimide (161 mg) in N, N-dimethylformamide (ImI) was stirred at ambient temperature for 4 hours. The reaction mixture was poured into a mixture of 10% sodium thiosulfate aqueous solution and chloroform. Then the organic layer was washed with saturated NaHCU3 aqueous solution, water, brine, dried over magnesium sulfate, and evaporated in vacuo. Resulting precipitates were collected by filtration and washed with diisopropyl ether to give 5-chloro-3-iodopyrazolo [ 1, 5-a] pyrimidine as an brown solid (180 mg) .1H-NMR(DMSO-d6)delta:7.42 ( IH, d, J=9.5Hz) , 7.97 ( IH, s) , 8.23 ( IH, d, J=9.2Hz) . MS:279 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,29274-24-6, its application will become more common.

Reference:
Patent; ASTELLAS PHARMA INC.; WO2007/13673; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 591-55-9, 5-Aminopyrimidine, 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

[00160] Step 1: Synthesis of tert-butyl 2-(tert-butyldimethylsilyloxy)-3-(3-(l-isopropyl- 4- (pyrimidin-5-ylamino)-lH-pyrazolo[3,4-b]pyridin-6-yl)-5-methoxyphenoxy) propyl(methyl)carbamate. A mixture of tert-butyl 2-(tert-butyldimethylsilyloxy)-3-(3-(7- chloro-3-isopropyl- pyrazolo[l,5-a]pyrimidin-5-yl)-5-methoxyphenoxy)-propyl(methyl)- carbamate (600 mg, 0.97 mmol); pyrimidin-5-amine (139 mg, 1.46 mmol); Pd2(dba)3 (136 mg, 0.194 mmol); BINAP (121 mg, 0.19 mmol) and NaOt-Bu (286 mg, 2.31 mmol) in 15 mL of dioxane was heated at 100 C under N2 for 14h. After cooling down to room temperature, water (30 mL) was added and the mixture was extracted with EtOAc (30 mL X 3). The organic phase was concentrated and the residue was purified by preparative TLC on silica gel developed with DCM/MeOH = 20: 1 to afford 2-(tert-butyldimethylsilyloxy)-3-(3-(l- isopropyl-4-(pyrimidin-5-ylamino)- lH- pyrazolo[3,4-b]pyridin-6-yl)-5- methoxyphenoxy)propyl (methyl)carbamate (190 mg, 29 % yield) as a pale yellow solid. ESI-LCMS (m/z): 678.3 [M+l]+.

The synthetic route of 591-55-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EPIZYME, INC.; CHESWORTH, Richard; MORADEL, Oscar Miguel; SHAPIRO, Gideon; DUNCAN, Kenneth W.; MITCHELL, Lorna Helen; JIN, Lei; BABINE, Robert E.; WO2014/144455; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 2915-16-4, 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.2915-16-4, name is 2-Chloro-4,6-diphenylpyrimidine, molecular formula is C16H11ClN2, molecular weight is 266.73, as common compound, the synthetic route is as follows.

TP2 is further reacted with 2-chloro-4,6-diphenylpyrimidine (1.0 equivalents, CAS: 2915-16-4), tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3 (0.03 equivalents; CAS 51364-51 -3), Tricyclohexylphosphine (PCy3; 0.07 equivalents, CAS 2622-14-2) and potassium phosphate tribasic (K3PO4, 1 .7 equivalents). The reaction mixture is stirred under nitrogen atmosphere in a dioxane/toluen e/water (6/1/1 ) mixture at 100 C overnight. After cooling down to room temperature (RT) the reaction mixture is extracted with DCM/brine. The organic phases are collected, washed with brine and dried over MgS04. The organic solvent is removed, the crude product was washed with cyclohexane and recrystallized from EtOH (Yield: 98%).

Statistics shows that 2915-16-4 is playing an increasingly important role. we look forward to future research findings about 2-Chloro-4,6-diphenylpyrimidine.

Reference:
Patent; CYNORA GMBH; SZAFRANOWSKA, Barbara; PINGEL, Patrick; BERGMANN, Larissa; AMBROSEK, David; KASPAREK, Christian; (0 pag.)WO2019/162332; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 1209459-16-4, Adding some certain compound to certain chemical reactions, such as: 1209459-16-4, name is 2-Bromopyrimidine-4-carbonitrile,molecular formula is C5H2BrN3, 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 1209459-16-4.

Example 11. Preparation of (3S)-tert-butyI 3-((l-(2-chIorophenyl)-2-((3,3- difluorocyclobutyl) amino)-2-oxoethyl)(3,5-difluorophenyl)carbamoyl)-4-(4- cyanopyrimid -2-yl)-5-oxopiperazine-l-carboxylate (racemic) – Compound 98 A mixture of (3S)-tert-butyl3-((l -(2-chlorophenyl)-2-((3,3-difluorocyclobutyl)amino)-2-oxoethyl) (3,5-difluorophenyl)carbamoyl)-5-oxopiperazine-l-carboxylate (200 mg, 0.326 mmol), 2- bromopyrimidine-4-carbonitrile (0.489 mmol), Pd2(dba)3 (30.2 mg, 0.0323 mmol), XantPhos (19.1 mg, 0.03 mmol) and Cs2C03 (148.7 mg, 0.46 mmol) in 1,4-dioxane (10 mL) was stirred at 80 C for 3 hr under N2. The reaction mixture was cooled to room temperature and filtered. The filtrate was concentrated and the residue was purified by a standard method to afford the desired product. NMR (400 MHz, CDC13): delta 8.97 (d, J= 4.3 Hz, 1H), 7.85-7.55 (d, 1H), 7.51-7.39 (m, 2H), 7.25 (t, J= 7.6 Hz, 1H), 7.13-6.26 (m, 6H), 5.91 (d, J= 7.6 Hz, 1H), 4.92-4.08 (m, 5H), 3.38 (t,J= 14.9 Hz, 1H), 3.02 (s, 2H), 2.83-2.22 (d, 2H), 1.61 (s, 9H). MS : 716.1 (M+l)+.

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. 1209459-16-4, 2-Bromopyrimidine-4-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AGIOS PHARMACEUTICALS, INC.; LEMIEUX, Rene M.; POPOVICI-MULLER, Janeta; TRAVINS, Jeremy M.; CAI, Zhenwei; CUI, Dawei; ZHOU, Ding; WO2015/10297; (2015); A1;,
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. 6299-25-8, name is 4,6-Dichloro-2-(methylthio)pyrimidine, the common compound, a new synthetic route is introduced below. Recommanded Product: 6299-25-8

Example 2C4,6-dichloro-2-(methylthio)pyrimidine-5-carboxylic acid; To a solution of diisopropylamine (20 mL, 142 mmol) in tetrahydrofuran (170 mL) at -78C was added n-butyl lithium (55.4 mL, 2.5M solution in hexane, 138 mmol). The mixture was stirred at -78C for 1 hour and was charged with a solution of the product of Example 2B (18 g, 92.3 mmol) in tetrahydrofuran (40 mL). After stirring at -78C for 3 hours, dry carbon dioxide was bubbled into the mixture for 30 minutes, followed by the addition of water at low temperature. The mixture was allowed to warm to ambient temperature and the mixture was adjusted to pH = 1 by addition of 2M hydrochloric acid. The mixture was extracted with ethyl acetate (3 x 300 mL) and the combined organic layers were dried over sodium sulfate, filtered and concentrated. The residue was washed with toluene to obtain the title compound. MS: 239 (M+H+).

The synthetic route of 6299-25-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBOTT LABORATORIES; VASUDEVAN, Anil; PENNING, Thomas; CHEN, Huanming; LIANG, Bo; WANG, Shaohui; WU, Fengchun; SHEN, Yan; LIU, Cuihua; ZOU, Zhenguang; WO2012/97478; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 938443-20-0, 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.938443-20-0, name is 2,4,7-Trichloropyrido[2,3-d]pyrimidine, molecular formula is C7H2Cl3N3, molecular weight is 234.4699, as common compound, the synthetic route is as follows.

The 2,4,7-trichloro-pyrido [2,3-d] pyrimidine (1g, 4.29mmol), and 8-oxa-3-azabicyclo [3.2.1] nonane hydrochloride (640mg, 4.29 mmol) were dissolved 20mLDCM added dropwise DIEA (0.9mL, 5.15mmol) under ice-cooling.After the reaction was stirred at room temperature for 18H, reaction mixture was washed, the organic layer was dried and concentrated to give a solid, which was used without purification was used directly in the next reaction.

The chemical industry reduces the impact on the environment during synthesis 938443-20-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Shandong Xuanzhu Pharmaceutical Technology co., LTD; WU, YONG QIAN; WANG, AI CHEN; (35 pag.)CN102887895; (2016); B;,
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.635698-56-5, name is tert-Butyl 2,4-dichloro-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate, molecular formula is C12H15Cl2N3O2, molecular weight is 304.17, as common compound, the synthetic route is as follows.name: tert-Butyl 2,4-dichloro-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate

To the mixture of tert-butyl 2,4-dichloro-7, 8-dihydropyrido[4,3 -d]pyrimidine6(5H)-carboxylate (4.00 g, 13.15 mmol) in CH2C12 (15.00 mL) was added HC1/dioxane (4 N,15.00 mL). The mixture was stirred at 15 C for 15 h. LCMS showed one main peak of desired product and about 5% of starting material. The mixture was stirred at 30 C for 1 h. LCMS showed desired product was major. The mixture was concentrated under reduced pressure to afford the title compound (3.07 g, crude, HC1 salt) as a white solid which was used in the next step without further purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,635698-56-5, tert-Butyl 2,4-dichloro-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; KADMON CORPORATION, LLC; OLSZEWSKI, Kellen; POYUROVSKY, Masha; BARSOTTI, Anthony; KIM, Ji-In; LIU, Kevin; MORRIS, Koi; (143 pag.)WO2016/210331; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 23631-02-9, 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. 23631-02-9, name is 4-Chloro-N,N-dimethylpyrimidin-2-amine. A new synthetic method of this compound is introduced below.

A mixture of N-(cis-4-bromo-2-trifluoromethoxy-benzyl)-cyclohexane-1, 4- diamine obtained in step B of example 1 (466 mg), (4-chloro-pyrimidin-2-yl)-dimethyl- amine (200 mg), and BuOH (1 mL) was stirred at reflux for 13 hr. The mixture was poured into saturated aqueous NaHC03 and the aqueous) layer was extracted with CHC13 (three times). The combined organic layer was dried over MgS04, filtered, concentrated under reduced pressure, and purified by flash chromttography (NH-silica gel, 20% EtOAc in) to give N4-(cis-4-{[4-bromo-2-(trifluoromethoxy) benzyl] arnino}-cyclohexyl)-Na, N2- dimethylpyrimidine-2, 4-diamine. To a solution of the above material in EtOAc (2 mL) was added 4 M hydrogen chloride in EtOAc (10 mL). The mixture was stirred at ambient temperature for 1 hr and concentrated under reduced pressure The residue was suspended in Et20 (20 mL) and the suspension was stirred at ambient temperature for 4 hr. The precipitate was collected by filtration, washed with Et2O, and dried under reduced pressure to give N4-(cis-4-{ [4-bromo-2-(trifluoromethoxy) benzyl]-amino} cyclohexyl)-N2, N2- dimethylpyrimidine-2, 4-diamine dihydrochloride (294 mg). ESI MS m/e 488, M (free) + H+ ;’H NMR (300 MHz, CDCI3) 8 1.42-1. 67 (m, 2 H), 2.03- 2.39 (m, 6 H), 2. 79-3.38 (m, 7 H), 4.13-4. 36 (m, 3 H), 6.89-7. 00 (m, 1 H), 7.42-7. 46 (m, 1 H), 7.50-7. 57 (m, 1 H), 7. 90-8. 01 (m, 1 H), 8.12 (d, J= 8.4 Hz, 1 H), 8.90-9. 00 (m, 1 H), 9.98-10. 18 (m, 2 H), 12.21-12. 37 (m, 1 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,23631-02-9, 4-Chloro-N,N-dimethylpyrimidin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; TAISHO PHARMACEUTICAL CO., LTD.; Arena Pharmaceuticals, Inc; WO2005/95357; (2005); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 1722-12-9 ,Some common heterocyclic compound, 1722-12-9, molecular formula is C4H3ClN2, 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 5 Synthesis of HK-9, HK-11, HK-13 and HK-15 The following describes the general synthesis of 2-(pyrrolidine-1-yl)pyrimidine (HK-9), 4,6-dimethoxy-2-(pyrrolidine-1-yl)pyrimidine, HK-11, 2-(piperidine-1-yl)pyrimidine (HK-13), 4,6-dimethoxy-2-(piperidine-1-yl)pyrimidine (HK-15), 5-benzyloxy-2-(pyrrolidine-1-yl)pyrimidine (Compound 35), 5-benzyloxy-2-(piperidine-1-yl)pyrimidine (Compound 36), 5-benzyloxy-4,6-dimethoxy-2-(pyrrolidine-1-yl)pyrimidine (Compound 37), and 5-benzyloxy-4,6-dimethoxy-2-(piperidine-1-yl)pyrimidine (Compound 38). Referring to the reaction scheme of , to 9.53 mL (116 mmol) pyrrolidine (29) in 400 mL of anhydrous THF was added 2.78 g of sodium hydride (116 mmol) and the mixture was refluxed for 0.5 hr. After cooling to r.t., 12 g (105 mmol) of 2-chloropyrimidine (33) was added dropwise and the mixture was refluxed for 2 days and then cooled in an ice bath. Water (200 mL) was then added to the cooled reaction mixture and the THF was removed in vacuo. The aqueous residue was extracted with CHCl3 and the combined CHCl3 extracts were washed with brine, dried over magnesium sulfate, and filtered. After removal of solvent in vacuo, the residue was purified by silica gel column chromatography using 20:1 hexanes:EtOAc as eluent. The product was then recrystallized from diethyl ether (Et2O) to give a 12.0 g (76%) of HK-9 as a yellow solid, mp 39.0-39.6 C. 1H NMR (CDCl3) delta 8.31 (d, J=4.88 Hz, 2H), 6.45 (t, J=4.88 Hz, 1H), 3.57 (t, J=4.4 Hz, 4H), 2.01-1.98 (m, 4H). Anal. Calcd for C8H11N3; C, 64.40; H, 7.43; N, 28.16. Found: C, 64.42; H, 7.53; N, 27.97.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1722-12-9, its application will become more common.

Reference:
Patent; KADOR, PETER F.; US2014/235858; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 5018-41-7, name is 4-Amino-6-chloro-5-methoxypyrimidine. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 5018-41-7

6-(4-(1 -(2-(azetidin-1 -yl)ethyl)-4-(2-(thfluoromethyl)Dvhdin-4-yl)-1 H-imidazol-2- yl)piperidin-1 -yl)-5-methoxypyrimidin-4-amine (“1 15”) A reaction mixture of 6-Chloro-5-methoxy-pyrimidin-4-ylamine (45.00 mg; 0.28 mmol; 1 .00 eq.), 4-[1 -(2-Azetidin-1 -yl-ethyl)-2-piperidin-4-yl-1 H-imidazol-4-yl]-2- trifluoromethyl-pyridine hydrochloride (4) (148.13 mg; 0.28 mmol; 1 .00 eq.), and Cs2C03 (367.53 mg; 1 .13 mmol; 4.00 eq.) in DMSO 1 .0ml was stirred at 120C for 2days, purified by HPLC collected title compound 17mg. LC-MS: (M+1 = 503, obsd. = 503).

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, 5018-41-7, 4-Amino-6-chloro-5-methoxypyrimidine.

Reference:
Patent; MERCK PATENT GMBH; LAN, Ruoxi; HUCK, Bayard R.; CHEN, Xiaoling; XIAO, Yufang; DESELM, Lizbeth Celeste; QIU, Hui; NEAGU, Constantin; BANKSTON, Donald; JONES, Christopher Charles Victor; WO2013/40059; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia