Month: August 2021

Electric Literature of 939986-65-9, 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.939986-65-9, name is 6-Chloropyrimidine-4-carbonitrile, molecular formula is C5H2ClN3, molecular weight is 139.5425, as common compound, the synthetic route is as follows.

A mixture of 6-chloropyrimidine-4-carbonitrile (153 mg, 1.10 mmol), Nphenylpiperidine-4-carboxamide hydrochloride 1 (221 mg, 0.914 mmol), K2C03 (253 mg, 1.83 mmol), THF (5 mL), and DMF (4 mL) was stirred at RT for 16 h. The mixture was concentrated under reduced pressure. The residue was partitioned between water, brine, and EtOAc. The organic layer was separated and the aqueous layer re-extracted with EtOAc. The combined organic layers were washed with brine, dried (Na2SO4), filtered, and the filtrate concentrated under reduced pressure to afford compound 2 (274 mg, 81%) as a white solid. LCMS Mass:308.0 (M+1).

Statistics shows that 939986-65-9 is playing an increasingly important role. we look forward to future research findings about 6-Chloropyrimidine-4-carbonitrile.

Reference:
Patent; PHARMAKEA, INC.; ROWBOTTOM, Martin, W.; HUTCHINSON, John, Howard; (185 pag.)WO2017/3862; (2017); 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. 105742-66-3, name is 4,5-Dichloro-2,6-dimethylpyrimidine, the common compound, a new synthetic route is introduced below. Recommanded Product: 4,5-Dichloro-2,6-dimethylpyrimidine

General procedure: Compound 5 was synthesized as described.33 Compounds 6 and 7were synthesized in our previous work.34 Compounds 4 (5 mmol), 7(5 mmol) and anhydrous potassium carbonate (5 mmol, 0.69 g) wereadded to a mixed solvent of dimethyl formamide (20 mL) and water(10 mL), and then refluxed for 2-4 h. The progress was monitored byTLC. After the reaction was complete, the reaction solution was pouredinto saturated saline and extracted with ethyl acetate (3×80 mL). Theextract was dried, filtered, and the solvent was removed under reducedpressure to give a crude product. Recrystallization from the mixedsolvent of petroleum ether and ethyl acetate gave pure target compoundsO1-17 (Scheme 2).

The synthetic route of 105742-66-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yan, Zhongzhong; Liu, Aiping; Ou, Yingcan; Li, Jianming; Yi; Zhang, Ning; Liu, Minhua; Huang, Lu; Ren, Jianwei; Liu, Weidong; Hu, Aixi; Bioorganic and Medicinal Chemistry; vol. 27; 15; (2019); p. 3218 – 3228;,
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.153435-63-3, name is 2-(Tributylstannyl)pyrimidine, molecular formula is C16H30N2Sn, molecular weight is 369.1328, as common compound, the synthetic route is as follows.Formula: C16H30N2Sn

A mixture of compound from step 20d (500 mg, 1.033 mmol), 2-(tri-n-butylstannyl)pyrimidine (395 mg,1.03 mmol), CsF (313 mg, 2.06 mmol) and Pd(PPh3)4 (115.5 mg,0.10 mmol), Cul (38 mg, 0.20 mmol) in DMF (7 mL) was stirred for 48 hours at 40 C. After being cooled to rt, it was concentrated and the residue was partitioned (EtOAc/brine). The organic was dried (Na2SO4), filtered and concentrated. The residue was chromatographed (silica, ethyl acetate/petroleum ether) to give the desired compound as a yellow solid (300 mg, 60%). ESIMS m/z = 486.25, 488.25 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,153435-63-3, 2-(Tributylstannyl)pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; ENANTA PHARMACEUTICALS, INC.; QIU, Yao-Ling; CAO, Hui; LI, Wei; PENG, Xiaowen; JIN, Meizhong; KASS, Jorden; GAO, Xuri; OR, Yat, Sun; (99 pag.)WO2017/11552; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 10397-13-4 ,Some common heterocyclic compound, 10397-13-4, molecular formula is C8H9Cl2N3O, 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 2 6-(4-Methanesulfonyl-piperazin-l-vI)-2-morphoHn-4-yl-[4,5’lbipyriinidinyl-2′-ylamine (4) A mixture of Intermediate Al (198mg), Intermediate G (230mg) and potassium carbonate (293mg) was stirred in acetonitrile (10ml) at room temperature. After 24 hours the reaction mixture was diluted with ethyl acetate, washed with water, dried (MgSO4) and the solvent removed in vacuo. The residue was recrystallised from ethyl acetate/hexane to yield 4-[4-chloro-6-(4-methanesulfonyl-piperazin-l-yl)-yrimidin-2- yl]-morpholine (206mg). Reaction of 4-[4-chloro-6-(4-methanesulfonyl-piperazin- 1 -yl)-yrimidin-2-yl]- morpholine with 2-aminopyrimidine-5-boronic acid, pinacol ester using standard Suzuki conditions yielded the desired title compound. IH NMR (400MHz, CDCl3) 2.80 (3H,s), 3.28-3.24 (4H,m), 3.82-3.75 (12H,m), 5.20 (2H,s,br.), 6.16 (lH,s), 8.91 (2H,s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,10397-13-4, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; WO2009/66084; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 90349-23-8, 5,7-Dimethylpyrazolo[1,5-a]pyrimidine-3-carboxylic 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, 90349-23-8, blongs to pyrimidines compound. Formula: C9H9N3O2

A solution of 5,7-dimethylpyrazolo[l,5-a]pyrimidine-3-carboxylic acid 2 (200 mg, 1.04 mmol) in DMF (5 mL) was charged with EDC.HC1 (240 mg, 1.25 mmol), HOBT (170 mg, 1.25 mmol), triethyl amine (0.43 mL, 3.14 mmol) and stirred at room temperature for 30 mins. To the resulting solution was added methyl 4-(4-aminophenyl)butanoate (240 mg, 1.25 mmol) and the mixture was stirred at room temperature for 16h. Then, the reaction mixture was quenched with ice-cooled water (50 mL) and stirred for another 30 mins. The solid was collected by filtration and washed with water followed by w-hexane and dried to afford the corresponding ester as a light brown solid (240 mg) which was used in the next step without further purification. ES-MS m/z 367.40 (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,90349-23-8, its application will become more common.

Reference:
Patent; LYSOSOMAL THERAPEUTICS INC.; SKERLJ, Renato, T.; LANSBURY, Peter, T.; GOOD, Andrew, C.; BOURQUE, Elyse, Marie Josee; (139 pag.)WO2016/73895; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 932-52-5, Adding some certain compound to certain chemical reactions, such as: 932-52-5, name is 5-Aminopyrimidine-2,4(1H,3H)-dione,molecular formula is C4H5N3O2, 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 932-52-5.

General procedure: A solution of 1.0 mmol of N-heterocyclic aldehyde in 10 mL of ethanol was added to a hot solution of 1.0 mmol of 5- or 6-aminouracil in 10 mL of DMSO. A few drops of glacial acetic acid were then added, and the mixture was refluxed for 6-8 h. The solution was cooled to room temperature, filtered, and evaporated to dryness using a rotary evaporator. The resulting solid was washed with cold ethanol followed by anhydrous diethyl ether.

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. 932-52-5, 5-Aminopyrimidine-2,4(1H,3H)-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Nair; Robinson; Trujillo; Russian Journal of Organic Chemistry; vol. 52; 3; (2016); p. 437 – 440; Zh. Org. Khim.; vol. 52; 3; (2016); p. 437 – 440,4;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 3680-69-1 ,Some common heterocyclic compound, 3680-69-1, 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.

Step 1: Synthesis of 4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidineTo a mixture of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (5 g, 32.6 mmol) in DMF (60 mL) under argon was added NIS (7.33 g, 32.6 mmol) at 0 C. The resulting mixture was stirred for 15 hours at 25 C under a atmosphere of argon in the darkness. The reaction mixture was poured into cold water and the mixture was filtered, the solid was washing with cold water (3 x 50 mL) and dried at 25 C to give 4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine as a solid. LC-MS: (ES, /// r): 279.9 [M+H]+ 1. H- MR: (400MHz, CD3SOCD3, pprn): 12.96 (brs, 1H), 8.62 (s, 1H), 7.95 (d, J= 1.8 Hz, 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. 3680-69-1, 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; GIRIJAVALLABHAN, Vinay M.; OLSEN, David B.; ZHANG, Zhibo; FU, Jianmin; TANG, Bing-Yu; WO2015/143712; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 58536-46-2, name is 4-(4-Bromophenyl)-2,6-diphenylpyrimidine, molecular formula is C22H15BrN2, 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. Formula: C22H15BrN2

F-4 8.0g (23.23mmol), 4- (4- bromophenyl) pyridine-2,6-diphenyl (4- (4-bromophenyl) -2,6-diphenylpyrimidine), 9.9g (25.55mmol), Pd2 (dba) 3 2.1g (2.323mmol), P (t-Bu) 3 0.22g (2.323mmol), sodium tert-butoxide 14.1g (69.69mmol) and stirred for 6 hours under the reflux of toluene in 120C 150mL. After cooled back to room temperature after completion of the reaction the solid is created filter was washed with ethyl acetate (EA), methanol (MeOH). Then after the solid boiled with excess Toluene filter to obtain the title compound 1-482 10.8g (71%).

With the rapid development of chemical substances, we look forward to future research findings about 58536-46-2.

Reference:
Patent; HEESUNG MATERIAL LTD.; LEE, JEONG HYEON; JONG, SOO JIN; KIM, KI YOUNG; KIM, DONG JOON; PARK, CHAN JOON; CHOI, JIN SEOK; CHOI, DAE HYEOK; EUM, SONG JIN; LEE, JOO DONG; (164 pag.)KR101579289; (2015); B1;,
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. 42754-96-1, name is 4,6-Dichloro-1H-pyrazolo[3,4-d]pyrimidine. A new synthetic method of this compound is introduced below., name: 4,6-Dichloro-1H-pyrazolo[3,4-d]pyrimidine

Compound 183a was prepared from tert-butyl 2,4-dichloro-5,6-dihydropyrido[3,4- d]pyrimidine-7(8H)-carboxylate (182a) (1.0 g, 3.29 mmol) in 2-Propanol (15 mL) using DIPEA (2.3 mL, 13.15 mmol) and 1-(3,4,5-trimethoxyphenyl)-1H-imidazol-4-amine (57a) (0.98 g, 3.95 mmol). This gave after workup and purification by flash column chromatography [silica gel, (12 g) eluting with DMA-80 in DCM (0 to 80%)] fert-butyl 2-chloro-4-((l-(3,4,5- trimethoxyphenyl)-lH-imidazol-4-yl)amino)-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)- carboxylate (183a) (0.87 g, 51 % yield) as a buff solid; NMR (300 MHz, DMSO-^e) delta 9.65 (s, 1H, D20 exchangeable), 8.16 (d, J = 1.5 Hz, 1H), 7.78 (d, J = 1.6 Hz, 1H), 6.90 (s, 2H), 4.35 (s, 2H), 3.87 (s, 6H), 3.69 (s, 3H), 3.61 (t, J = 5.8 Hz, 2H), 2.69 – 2.60 (m, 2H), 1.43 (s, 9H).

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, 42754-96-1, 4,6-Dichloro-1H-pyrazolo[3,4-d]pyrimidine.

Reference:
Patent; BIOCRYST PHARMACEUTICALS, INC.; KOTIAN, Pravin, L.; BABU, Yarlagadda, S.; KUMAR, V., Satish; ZHANG, Weihe; LU, Peng-Cheng; RAMAN, Krishnan; (747 pag.)WO2018/232094; (2018); 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. 5413-85-4, name is 5-Amino-4,6-dichloropyrimidine. A new synthetic method of this compound is introduced below., Safety of 5-Amino-4,6-dichloropyrimidine

General procedure: [00532] The mixture of 4,6-dichloropyrimidine-5-amine (A-2) (16.0 g, 98.2 mmol) and sodium hydrosulphide (7.15 g, 128 mmol) in MeOH (320 mL) is stirred at reflux for 3 h. The reaction is complete based on TLC analysis. The reaction mixture is allowed to cool to RT and then concentrated in vacuo. The residue is poured into aqueous NaOH solution (1M, 200 mL) and then neutralized with acetic acid to adjust the pH to 5-6. The resulting mixture is stirred at RT for 30 min. The solid is collected by filtration, rinsed with water (2 x 50 mL) and dried in vacuo to afford the product, 5-amino-6-chloropyrimidine-4-thiol (A-3).

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, 5413-85-4, 5-Amino-4,6-dichloropyrimidine.

Reference:
Patent; INFINITY PHARMACEUTICALS INC.; INTELLIKINE, LLC; CASTRO, Alfredo, C.; EVANS, Catherine, A.; LESCARBEAU, Andre; LIU, Tao; SNYDER, Daniel, A.; TREMBLAY, Martin, R.; REN, Pingda; LIU, Yi; LI, Liansheng; CHAN, Katrina; WO2013/12918; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia