Day: March 23, 2022

Application of 53557-69-0 , The common heterocyclic compound, 53557-69-0, name is 6-Iodopyrimidin-4-amine, molecular formula is C4H4IN3, 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: A flask containing a solution of 55-iodide (4.09g, 18.5mmol) in NMP (75ml) was purged with argon for 5min. Zinc cyanide (2.28g, 19.4mmol) and tetrakis(triphenylphosphine)palladium (0) (1.71g, 1.48mmol) were added and the mixture was stirred at 80C for 2h. The mixture was cooled to room temperature, EtOAc (200ml) and 30% aqueous NH4OH (200ml) was added, and stirring was continued for 1h. The layers were separated, the aqueous layer was extracted with EtOAc (4×200ml), and the combined organic layers were concentrated under reduced pressure. Et2O (30ml) was added and the precipitate was collected by filtration and washed with Et2O to deliver 2-aminopyrimidine-4-carbonitrile (1.66g, 13.8mmol, 75% yield) as a white solid.

The synthetic route of 53557-69-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Reichelt, Andreas; Bailis, Julie M.; Bartberger, Michael D.; Yao, Guomin; Shu, Hong; Kaller, Matthew R.; Allen, John G.; Weidner, Margaret F.; Keegan, Kathleen S.; Dao, Jennifer H.; European Journal of Medicinal Chemistry; vol. 80; (2014); p. 364 – 382;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 29274-18-8, 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. 29274-18-8, name is Ethyl 7-oxo-4,7-dihydropyrazolo[1,5-a]pyrimidine-6-carboxylate. A new synthetic method of this compound is introduced below.

A suspension of ethyl 7-oxo-4,7-dihydropyrazolo[l,5-a]pyrimidine-6- carboxylate (1.9 g, 9.2 mmol) in 10% aq. NaOH (12 mL, 30.0 mmol) was refluxed for 2 hours. The reaction mixture was allowed to cool to room temperature; the solution was acidified to pH 3-4 with 6 M HCl. The forming precipitate was filtered, washed with water and dried to afford 7-oxo-4,7-dihydropyrazolo[l,5-a]pyrimidine-6-carboxylic acid; 1.6 g (97%). 1H NMR (300 MHz, DMSO) delta 8.53 (s, 1 H), 7.94 (d, J= 1.8 Hz, 1 H), 6.32 (d, J= 1.8 Hz, 1 H). MS (ESI) m/z: 177.9 [M-H]”.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,29274-18-8, Ethyl 7-oxo-4,7-dihydropyrazolo[1,5-a]pyrimidine-6-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2009/76593; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 23945-50-8 ,Some common heterocyclic compound, 23945-50-8, molecular formula is C5H4N2O3S, 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 Under an atmosphere of nitrogen, an acetonitrile solution (30 ml) of methacryloyl chloride (20.9 g, 0.2 mol) was slowly added dropwise at room temperature, using a dropping funnel, to 1,6-hexanediol (47.3 g, 0.40 mol), molecular sieve 3A powder (40 g) and acetonitrile (470 ml) in a 1-L three-necked flask. After the completion of the dropwise addition, the mixture was refluxed with heating for 5 hours. The mixture was then left alone to cool to room temperature, the molecular sieve 3A powder was filtered out from the reaction mixture, and acetonitrile was distilled off under reduced pressure from the filtrate. Methylene chloride (300 ml) was added to the residue, and the resultant methylene chloride solution was washed with water. The methylene chloride layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. 6-Hydroxyhexyl methacrylate (33.3 g) was separated and purified as a colorless transparent liquid from this residue by silica gel column chromatography. 6-Hydroxyhexyl methacrylate (5.59 g, 30 mmol), N,N’-di cyclohexylca rbodii mide (2.27 g, 11 mmol), 5-carboxy-2-thiouracil (1.72 g, 10 mmol) and tetrahydrofuran (50 ml) were put in a 200-ml three-necked flask to make a solution, and the solution was continuously stirred at room temperature for 3 days. A white precipitate was formed as the reaction progressed, and after the completion of the reaction, the white precipitate was filtered out. Then the same separation and purification operations were carried out as in Example 1 to give 6-methacryloyloxyhexyl 2-thiouracil-5-carboxylate [B] (1.13 g, 3.3 mmol) repre- sented by the following formula. The results of NMR (d6DMSO), MASS and elementary analysis are shown below. MASS (M+1)+=341

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. 23945-50-8, 4-Oxo-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TOKUYAMA CORPORATION; EP802194; (1997); A3;,
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. 17326-27-1, name is 2-Chloro-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carbaldehyde, the common compound, a new synthetic route is introduced below. Recommanded Product: 17326-27-1

G2 (0.5 mmol) was dissolved in 10.4 mL of tert-butyl alcohol and 2.5 mL of 2-methyl-2- butene. A solution of sodium chlorite (4.59 mmol) and sodium dihydrogenphosphate (3.46 mmol) in 4.2 mL of water was added dropwise. The reaction mixture was stirred at room temperature overnight. Volatile components were then removed under vacuum, and the residue was dissolved in 10 ml of water and extracted with two 10 ml portions of hexane. The aqueous layer was acidified to pH=3 with HCl(aq) and extracted with 10 mL portions of methylene chloride. The combined organic layers were washed with 20 mL of cold water, dried and concentrated to give G4.; 2-Chloro-9-methyl-4-oxo-4H-pyrido Gamma 1.2-a1pyrimidine-3 -carboxylic acid ( 144) NMR (400 MHz, OMSO-d6) delta 2.58 (s, 3H), 7.53 (t, J = 7.0 Hz, 1H), 8.14 (d, J = 7.2 Hz, 1H), 8.97 (d. J= 6.8 Hz, 1H), 13.53 (brs, 1H); 13C NMR (100 MHz, DMSO-i/6) delta 16.7, 108.1, 1 17.1, 125.6, 133.3, 138.7, 148.2, 152.0, 154.6, 163.9.

The synthetic route of 17326-27-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; INSTITUT PASTEUR KOREA; INSTITUT NATIONAL DE LA SANTE ET DE LA RECHERCHE MEDICALE (INSERM) (EPST); NO, Zaesung; KIM, Jaeseung; BRODIN, Priscille; SEO, Min Jung; PARK, Eunjung; CECHETTO, Jonathan; JEON, Heekyoung; GENOVESIO, Auguste; LEE, Saeyeon; KANG, Sunhee; EWANN, Fanny, Anne; NAM, Ji, Youn; FENISTEIN, Denis, Philippe, Cedric; CHRISTOPHE, Thierry; CONTRERAS DOMINGUEZ, Monica; KIM, EunHye; HEO, Jamung; WO2011/85990; (2011); 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.71149-52-5, name is 4-Chloro-2-methyl-7H-pyrrolo[2,3-d]pyrimidine, molecular formula is C7H6ClN3, molecular weight is 167.6, as common compound, the synthetic route is as follows.Recommanded Product: 71149-52-5

To a solution of 4-chloro-2-methyl-7H-pyrrolo[2,3-d]pyrimidine (400 mg, 2.4 mmol) in dichloromethane (10 mL) was added N-iodosuccinimide (537 mg, 2.39 mmol).The mixture was stirred at room temperature for 2 hours, then washed with aqueous sodium sulfite solution, dried over sodium sulfate, filtered, and concentrated in vacuo to provide the product as a brown solid. Yield: 330 mg, 1.12 mmol, 47%. LCMS m/z 293.8 [M+H].

At the same time, in my other blogs, there are other synthetic methods of this type of compound,71149-52-5, 4-Chloro-2-methyl-7H-pyrrolo[2,3-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; PFIZER INC.; GALATSIS, Paul; HAYWARD, Matthew Merrill; HENDERSON, Jaclyn; KORMOS, Bethany Lyn; KURUMBAIL, Ravi G; STEPAN, Antonia Friederike; VERHOEST, Patrick Robert; WAGER, Travis T.; ZHANG, Lei; WO2014/1973; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 890094-38-9, 2-Chloro-N-isopropyl-5-nitropyrimidin-4-amine, 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, Product Details of 890094-38-9, blongs to pyrimidines compound. Product Details of 890094-38-9

4-amino-N-(4-methylpiperidin-1-yl)benzamide(4.6g) was added to a solution of Compound 2-3(4.3g) in n-butanol(150ml). The mixture was reacted at 90C for 4.5 hours, cooled to room temperature, filtered, washed and dried to obtain a yellow solid(5.7g) in a yield of 70.0%. 1H NMR(400 MHz, DMSO-d6): delta 10.58(s, 1H), 9.02(s, 1H), 8.48(d, J=5.6Hz, 1H), 8.20(d, J=6.8Hz, 1H), 7.86(m, 4H), 4.45(m, 1H), 3.80(m,1H), 2.94(br, 4H), 2.32(s, 3H), 1.62-1.83(m, 4H), 1.33(d, J=6.4Hz, 6H)ppm.

The synthetic route of 890094-38-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Si Chuan University; CSPC Zhongqi Pharmaceutical Technology (Shijiazhuang) Co., Ltd.; YANG, Shengyong; WEI, Yuquan; EP2578584; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 216309-28-3, 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. 216309-28-3, name is 5-((Trimethylsilyl)ethynyl)pyrimidine, molecular formula is C9H12N2Si, 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.

S8b) 3,-Dideoxy-3-i4-(l,3-pyrimidin-5-yl)-lH-l,2,3-triazol-l-yll-3,-i4-(3,4,5- trifluorophenyl)-lH-l,2,3-triazol-l-yll-l.,l ‘-sulfanediyl-di-B-D-galactopyranosideIntermediate 1 (92 mg) and 5-[2-(trimethylsilyl)ethynyl]-pyridine (65 mg) was dissolved in MeCN (5 mL, dry) and stirred at r.t. Copper(I) iodide (24 mg) was added followed by Hunig’s base (65 mu) and the mixture was heated to 50 C. After 18 h cesium fluoride (5 mg) was added and the temperature increased to 70 C. After 24 h the mixture was filtered and concentrated. The residue was purified by HPLC (Xterra/MeCN:H20:25 mM NH3). Freezedrying afforded the title compound as a white solid (73 mg). H NMR (400 MHz, Methanol-i4) delta 9.24 (s, 2H), 9.13 (s, 1H), 8.76 (s, 1H), 8.58 (s, 1H), 7.65 – 7.56 (m, 2H), 5.01 – 4.88 (m, 4H), 4.75 (q, J= 10.3 Hz, 2H), 4.17 (dd, J = 8.7, 2.4 Hz, 2H), 3.95 – 3.78 (m, 4H), 3.73 (dd, J= 11.3, 3.5 Hz, 2H). ESI-MS m/z calcd for [C26H28F3N808S]+(M+H)+: 669.16; found: 669.15.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 216309-28-3, 5-((Trimethylsilyl)ethynyl)pyrimidine.

Reference:
Patent; GALECTO BIOTECH AB; ZETTERBERG, Fredrik; NILSSON, Ulf; LEFFLER, Hakon; BRIMERT, Thomas; JOHNSSON, Richard; VERMA, Priya; (71 pag.)WO2016/113335; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 199678-12-1, 4-Pyrimidin-2-yl-benzoic 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, 199678-12-1, blongs to pyrimidines compound. COA of Formula: C11H8N2O2

Into a 250-mL round-bottom flask, was placed (2S)-2-amino-5-[[(1R,2S)-2-(4-fluorophenyl)cyclopropyl](prop-2-en-1-yl)amino]-1-(4-methylpiperazin-1-yl)pentan-1-one (1.04 g, 2.68 mmol, 1.00 equiv), dichloromethane (50 mL), HATU (1.71 g, 4.50 mmol, 1.68 equiv), DIEA (1.16 g, 8.98 mmol, 3.35 equiv). This was followed by the addition of a solution of 4-(pyrimidin-2-yl)benzoic acid (450 mg, 2.25 mmol, 0.84 equiv) in CH2Cl2 (5 mL) dropwise with stirring at 0 C. The resulting solution was stirred overnight at room temperature. The resulting mixture was concentrated under vacuum. The resulting solution was extracted with 3×50 mL of EtOAc and the organic layers combined. This resulted in 0.52 g (34%) of N-[(2S)-5-[[(1R,2S)-2-(4-fluorophenyl)cyclopropyl](prop-2-en-1-yl)amino]-1-(4-methylpiperazin-1-yl)-1-oxopentan-2-yl]-4-(pyrimidin-2-yl)benzamide as a red solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,199678-12-1, its application will become more common.

Reference:
Patent; Imago Biosciences, Inc.; Rienhoff, JR., Hugh Y.; McCall, John M.; Clare, Michael; Celatka, Cassandra; Tapper, Amy E.; (226 pag.)US2016/237043; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 914916-98-6, 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 914916-98-6, name is 6-Amino-5-chloro-4-pyrimidinecarboxylic acid. This compound has unique chemical properties. The synthetic route is as follows.

In a 100 mL round-bottom flask, 23.2 (1.21 g, 0.00697 mole), methyl 2-(1-aminoethyl)thiazole-5-carboxylate (1.30 g, 0.00697 mole), and TBTU (2.69 g, 0.00837 mole) were dissolved in N,N-dimethylformamide (25.0 mL, 0.323 mole) to which was added N,N-diisopropylethylamine (3.64 mL, 0.0209 mole). The resulting yellow brown solution was allowed to stir at RT for 3 hr. The reaction mixture was diluted with 250 mL EtOAc, washed with 75 mL satd. NaHCO3 (2×), 75 mL of water, and 50 mL brine. The organic layer was dried over Na2SO4 and concentrated to a brown oil. The residue was purified by flash column chromatography (50% EtOAc/Hexanes gradient to 100% EtOAc) to yield 1.12 g (0.0070 47%) of desired product 23.3. LCMS m/z 342 [M+1]+.

According to the analysis of related databases, 914916-98-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sunesis Pharmaceuticals, Inc.; US2009/36419; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 34415-10-6, 2-Methyl-6-oxo-1,6-dihydropyrimidine-4-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, Quality Control of 2-Methyl-6-oxo-1,6-dihydropyrimidine-4-carboxylic acid, blongs to pyrimidines compound. Quality Control of 2-Methyl-6-oxo-1,6-dihydropyrimidine-4-carboxylic acid

Preparation of 6-chloro-2-methylpyrimidine-4-carbonyl chloride:To 920 mg (5.97 mmol) of 6-hydroxy-2-methylpyrimidine-4-carboxylic acid was added 13 mL of POCl3. The mixture was heated at reflux for 1 h, then concentrated in vacuo to a brown oil. This was suspended in 25 mL of pentane and extracted with water (2 x 10 mL). The combined water layers were back extracted with pentane (1 x 25 mL), then the combined pentane layers were washed again with water (2 x 10 mL), dried over MgSO4, filtered, and concentrated to 494 mg (43%) of a colorless oil.

The synthetic route of 34415-10-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SIRTRIS PHARMACEUTICALS, INC.; WO2009/61453; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia