Day: June 23, 2021

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.1753-50-0, name is 2-Chloropyrimidine-5-carbonitrile, molecular formula is C5H2ClN3, molecular weight is 139.54, as common compound, the synthetic route is as follows.Quality Control of 2-Chloropyrimidine-5-carbonitrile

To a stirred solution of compound GV (0.5 g, 1.78 mmol) and 2-chloropyrimidine-5-carbonitrile (AF, 0.37 g, 2.67 mmol) in EtOH (20 mL) was added DIPEA (0.96 mL, 5.35 mmol) and the reaction mixture was stirred at 90C for 14 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was concentrated under reduced pressure. The crude product was purified by silica gel column chromatography using 2% MeOH/DCM to afford compound GW (0.35 g, 51.0%) as an off white solid. 1H NMR (400 MHz, DMSO-d6): _ 8.80 (d, = 8.4 Hz , 1H), 8.69 (s, 2H), 7.46 – 7.39 (m, 2H), 7.38-7.14 (m, 4H), 5.23-5.18 (m, 1H), 3.41-3.37 (m, 1H), 3.30-3.25 (m, 1H), 2.83 (s, 3H); LC-MS: m/z 384.05 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1753-50-0, 2-Chloropyrimidine-5-carbonitrile, and friends who are interested can also refer to it.

Reference:
Patent; VPS-3, INC.; YATES, Christopher, M.; (397 pag.)WO2018/165520; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 3177-24-0, 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. 3177-24-0, name is 2,4-Dichloropyrimidine-5-carbonitrile, molecular formula is C5HCl2N3, 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: DIPEA (0.86mmol) was added to the solution of 2,4-dichloropyrimidine-5-carnonitrile (0.57mmol) in DMF (0.5ml) and stirred at room temperature for 10min. A solution of aminobenzene reagent corresponding to desired product (0.57mmol) in DMF (0.5ml) was added dropwise to the reaction mixture and stirred for 1h. The resultant was evaporated under vacuum and extracted with EtOAc. The organic layer was collected, washed with brine, dried over MgSO4, filtered, and dried under reduced pressure. 4c was obtained from the reaction of 4b, whereby substitution at the 2-position occurred.

According to the analysis of related databases, 3177-24-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Phuangsawai, Oraphan; Beswick, Paul; Ratanabunyong, Siriluk; Tabtimmai, Lueacha; Suphakun, Praphasri; Obounchoey, Phongphat; Srisook, Pimonwan; Horata, Natharinee; Chuckowree, Irina; Hannongbua, Supa; Ward, Simon E.; Choowongkomon, Kiattawee; Gleeson, M. Paul; European Journal of Medicinal Chemistry; vol. 124; (2016); p. 896 – 905;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 56-09-7, 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. 56-09-7, name is 2-Amino-6-hydroxypyrimidin-4(3H)-one. A new synthetic method of this compound is introduced below.

Phosphorus oxychloride (58.7mL, 630mmol) was added to a 500mL single-necked round bottom flask, N, N-dimethylformamide (12.1mL, 157mmol) was added dropwise at a low temperature bath of 5 C, and then transferred to 25 C , 2-Amino-4,6-dihydroxypyrimidine (10g, 78.7mmol) was added in portions, and the temperature was raised to 100 C to react for 5 hours. The reaction was stopped, most of the phosphorus oxychloride was removed by rotary evaporation under reduced pressure, water (900 mL) was added, and the mixture was stirred at 25 C for 32 hours, filtered, and the resulting solid was added to ethyl acetate (50 mL). After stirring for 30 minutes, Filter and dry the filter cake to give the title compound as a yellow solid (12.2 g, 80.8%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,56-09-7, 2-Amino-6-hydroxypyrimidin-4(3H)-one, and friends who are interested can also refer to it.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Shenzhen Dongyangguang Pharmaceutical Co., Ltd.; Jin Chuanfei; Zhong Wenhe; Deng Kang; (40 pag.)CN111072675; (2020); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 3438-46-8 ,Some common heterocyclic compound, 3438-46-8, molecular formula is C5H6N2, 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 A-Preparation of pyrimidine-4-yl formaldehyde Pyrimidine-4-yl formaldehyde was prepared from 4-methyl pyrimidine through a reference described in M. C. Liu et al., J Med Chem., 1995, 38 (21), 4234-4243.

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. 3438-46-8, 4-Methylpyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Amgen Inc.; US6878714; (2005); B2;,
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. 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. Computed Properties of C13H13Cl2N3O2S

2,5-dichloro-N-(2-(isopropylsulfonyl)phenyl)py-rimidine-4-amine (472 mg, i.36 mmol) was dissolved in0.08 M HC1-ethoxyethanol (i .0 mE), to which the compound (200 mg, i . i3 mmol) prepared in preparative example 20 was added, followed by stirring at 80 C. for i2 hours. The reaction mixture was cooled to room temperature, neutralized with sodium hydrogen carbonate aqueous solution, and extracted twice with ethylacetate. The extracted organic layer was dried over sodium sulfate and then filtered. The solvent was eliminated by distillation under reduced pressure. Then, purification was performed by silica gel colunm chromatography (eluent: methanol/ dichioromethane, i/9) to give the target compound 2-(4-((5- chioro-4-((2-(isopropylsulfonyl)phenyl)amino)pyrimidine- 2-yl)amino)-5-methoxy-2-methylphenyl)acetonitrile as a white solid (450 mg, 0.926 mmol, yield: 8i%).10581] ?H-NMR (300 MHz, CDC13) oe 9.53 (s, br, iH),8.53 (d, J=8.3 Hz, iH), 8.i8 (s, iH), 8.i3 (s, iH), 7.94 (d, J=7.9 Hz, iH), 7.64 (t, J=8.4 Hz, iH), 7.55 (s, br, iH), 7.28 (t, J=7.8 Hz, iH), 6.86 (s, iH), 3.9i (s, 3H), 3.63 (s, 2H), 3.26 (sept, J=6.9 Hz, iH), 2.i7 (s, 3H), i.3i (d, J=6.9 Hz, 6H); EC/MS 485.9 [M+H].

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, 761440-16-8, 2,5-Dichloro-N-(2-(isopropylsulfonyl)phenyl)pyrimidin-4-amine.

Reference:
Patent; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; Kim, Pilho; Kim, Hyoung Rae; Cho, Sung Yun; Ha, Jae Du; Jung, Hee Jung; Yun, Chang Soo; Hwang, Jong Yeon; Park, Chi Hoon; Lee, Chong Ock; Ahn, Sunjoo; Chae, Chong Hak; (97 pag.)US2018/111905; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 13036-57-2, 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. 13036-57-2, name is 2-Chloro-4-methylpyrimidine, molecular formula is C5H5ClN2, 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.

Example 1, Step E1e 1f[0067] A mixture of compound 1e (68 mg, 0.2 mmol), 2-chloro-4-methylpyrimidine (31 mg, 0.24 mmol), Pd2(dba)3 (22.85 mg, 0.025 mmol), Xant-phos (28.9 mg, 0.05 mmol) and Cs2C03 (98 mg, 0.3 mmol) in dioxane (3 mL) was heated to reflux under N2 for 4 hrs. After cooling to r.t., the mixture was diluted with H20 (10 mL) and extracted with EtOAc (10 ml_x2), the combined organic layers were dried over Na2S04, concentrated in vacuo and purified by preparative TLC (EtOAc: PE = 2:1 ) to give product 1f (62.4 mg, 75%).[0068] This compound was characterized by mass spectroscopy (MS) in accordance with the procedure described herein. Results of MS indicated MS (ESI): m/z 433(M+H)+

According to the analysis of related databases, 13036-57-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ADDEX PHARMA SA; LIVERTON, Nigel, J.; BOLEA, Christelle; CELANIRE, Sylvain; LUO, Yunfu; WO2012/6760; (2012); 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. 115581-36-7, name is 2-Chloro-5-(methylthio)pyrimidine, the common compound, a new synthetic route is introduced below. SDS of cas: 115581-36-7

m-CPBA (545 mg, 3.15 mmol) was added to a stirred mixture of 2-chloro-5- (methylthio)pyrimidine (340 mg, 2.1 mmol) in DCM (20 mL). The resulting mixture was stirred for 10 minutes at rt, quenched by the addition of aqueous NaHCCh (10%, 40 mL), and extracted with DCM (3 x 50 mL). The combined organic layers was washed with brine (50 mL), dried over anhydrous NaiSCL, filtered, and concentrated under vacuum. The residue was purified by column chromatograph (EA in PE from 0% to 30%) to afford 2-chloro-5- (methylsulfonyl)pyrimidine (120 mg, 30% yield) as a white solid. LCMS (m/z) 193 (M+H)+, retention time: 0.56 min, LC/MS Method 9

The synthetic route of 115581-36-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; FOX, Ryan Michael; HARRIS, Philip Anthony; HOLENZ, Joerg; SEEFELD, Mark Andrew; ZHOU, Ding; (119 pag.)WO2019/130230; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 90905-33-2, Adding some certain compound to certain chemical reactions, such as: 90905-33-2, name is 2-Methylpyrimidine-5-carbaldehyde,molecular formula is C6H6N2O, 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 90905-33-2.

2-Methylpyrimidine-5-carbaldehyde (0.27 g, 2.21 mmol) was dissolved in EtOH (40 mL), and 4-acetylpyridine (0.57 mL, 0.62 g, 5 mmol) was added followed by crushed solid KOH (0.33 g, 5.90 mmol) after which the solution turned red. Aqueous NH3 (25percent in water, 13.9 mL, 90 mmol) was added dropwise and the mixture stirred overnight at ambient temperature. A yellow precipitate formed which was separated by filtration, washed with water (3 * 7 mL) and ethanol (3 * 7 mL) and recrystallized from chloroform/methanol. Compound 4 was obtained as a white solid (0.26 g, 0.78 mmol, 32percent). Decomposition > 260 °C. 1H NMR (500 MHz, CDCl3) ?/ppm 9.02 (s, 2H, HC4), 8.83 (m, 4H, HA2), 8.09 (m, 4H, HA3), 8.01 (s, 2H, HB3), 2.87 (s, 3H, HMe); 13C{1H} NMR (126 MHz, CDCl3) ?/ppm 169.3 (CC2), 155.9 (CA4), 155.14 (CC4), 150.8 (CB4) 150.7 (CA2), 145.3 (CB2), 128.5 (CC5), 121.1 (CA3), 118.3 (CB3), 25.9 (CMe); IR (solid, nu/cm-1) 3077 (w), 3033 (w), 1609 (m), 1594 (s), 1569 (m), 1549 (m), 1544 (m), 1539 (m), 1531 (m), 1464 (s), 1461 (s), 1456 (s), 1447 (m), 1432 (m), 1429 (m), 1423 (m), 1404 (m), 1377 (m), 1373 (m), 1368 (m), 1247 (m), 1064 (m), 1028 (m), 999 (m), 995 (m), 895 (m), 851 (m), 844 (m), 835 (s), 791 (m), 739 (m), 731 (m), 670 (m), 664 (m), 649 (m), 637 (s), 629 (s), 619 (m), 616 (m), 604 (m), 597 (m), 582 (m), 570 (m), 564 (m), 543 (m), 541 (m), 535 (m), 528 (m), 523 (m), 519 (m), 513 (s), 506 (s), 502 (s). UV-Vis (MeCN, 2.5 * 10-5 M) lambda/nm (epsilon/dm3 mol-1 cm-1) 247 (44 458), 312 (7856). ESI-MS m/z 326.3 [M+H]+ (calc. 326.1). Found: C, 69.04; H, 4.75; N, 20.22; required for C20H15N5.H2O C, 69.96; H, 4.99; N, 20.40.

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. 90905-33-2, 2-Methylpyrimidine-5-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Maximilian Klein; Constable, Edwin C.; Housecroft, Catherine E.; Zampese, Jennifer A.; Polyhedron; vol. 81; (2014); p. 98 – 104;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 32779-38-7, 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. 32779-38-7, name is 2-Chloro-5-iodopyrimidine. A new synthetic method of this compound is introduced below.

To a mixture of compound 1 (5 g, 20.80 mmol, 1 eq) and ethynyl(trimethyl)silane (4.09 g, 41.59 mmol, 5.76 mL, 2 eq) in THF (50 mL) was added CuI (118.82 mg, 623.88 umol, 0.03 eq) , Pd(PPh3)2Cl2 (437.90 mg, 623.88 umol, 0.03 eq) and Et3N (4.21 g, 41.59 mmol, 5.79 mL, 2 eq) under N2. The mixture was purged with N2 for three times and stirred at 50C for 12 hrs under N2. TLC showed it was finished (Petroleum ether: Ethyl acetate = 5: 1 Rf = 0.24). It was concentrated directly. The residue was purified by column chromatography (SiO2, Petroleum ether/Ethyl acetate = 8: 1, Petroleum ether: Ethyl acetate = 5: 1, Rf = 0.43) to give [00544] Compound 2 (2 g, 9.49 mmol, 45.64% yield) was obtained as a brown solid

At the same time, in my other blogs, there are other synthetic methods of this type of compound,32779-38-7, 2-Chloro-5-iodopyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; KLEO PHARMACEUTICALS, INC.; BUNIN, Anna; IBEN, Lawrence G.; MANION, Douglas; SPIEGEL, David Adam; WELSCH, Matthew Ernest; (397 pag.)WO2019/136442; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 932-52-5 ,Some common heterocyclic compound, 932-52-5, molecular formula is C4H5N3O2, 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.

General procedure: To a mixture of 5-aminouracil (127 mg, 1 mmol) with an appropriate aldehyde (241 mg, 1.2 mmol) in methanol (15 mL) were added few drops of glacial acetic acid. The reaction mixture was stirred at room temperature until 5-aminouracil was completely consumed (TLC). The precipitate was filtered off, washed with methanol and air dried to give the corresponding product 1-10 as a yellow solid.

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; Koz; Russian Journal of General Chemistry; vol. 89; 1; (2019); p. 122 – 127; Zh. Obshch. Khim.; vol. 89; 1; (2019); p. 122 – 127,6;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia