Day: March 18, 2022

Reference of 14631-08-4 , The common heterocyclic compound, 14631-08-4, name is 2-Chloropyrimidine-4,5-diamine, molecular formula is C4H5ClN4, 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.

Compound 21-3 (4 g, 27.6 mmol) and compound 21-3-1 (5.2 g, 31.2 mmol) were dissolved in HCl/i-PrOH (2 mL/40 mL), and the mixture was heated to 100 C. and stirred for 14 h, followed by adjusted to pH 9 with Na2CO3 (aq.) and extracted with DCM (50 mL×4). The organic phase was dried over anhydrous Na2SO4, filtered and concentrated to give a crude product which was purified by column chromatography to afford compound 21-4 (1.1 g, Yield 14.7%) as black solid.

The synthetic route of 14631-08-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hubei Bio-Pharmaceutical Industrial Technological Institute Inc.; Humanwell Healthcare (Group) Co., Ltd.; Wang, Xuehai; Wu, Chengde; Xu, Yong; Shen, Chunli; Li, Li’e; Hu, Guoping; Yue, Yang; Li, Jian; Guo, Diliang; Shi, Nengyang; Huang, Lu; Chen, Shuhui; Tu, Ronghua; Yang, Zhongwen; Zhang, Xuwen; Xiao, Qiang; Tian, Hua; Yu, Yanping; Chen, Hailiang; Sun, Wenjie; He, Zhenyu; Shen, Jie; Yang, Jing; Tang, Jing; Zhou, Wen; Yu, Jing; Zhang, Yi; Liu, Quan; (251 pag.)US2017/313683; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 17180-94-8, Adding some certain compound to certain chemical reactions, such as: 17180-94-8, name is 5-Chloropyrimidine,molecular formula is C4H3ClN2, 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 17180-94-8.

A 100 mL round-bottom flask was charged with 5-chloropyrimidine (5 mmol), phenylboronic acid (1.22 g, 10 mmol), PPh3 (265 mg, 1 mmol) and Pd(OAc)2 (224 mg, 1 mmol) in dioxide (50 mL) under nitrogen at room temperature. After stirring for 30 minutes, Na2C03 (159 mg, 7.5 mmol) and H20 (10 mL) were added and the resulting mixture was heated at reflux for 3 h. After cooling to rt, the reaction mixture was poured into water and extracted with EtOAc (3 x 50 mL). The combined organic layers were washed with brine (3 x 50 mL) and dried over anhydrous Na2S04. After filtration and concentration, the crude product was purified by column chromatography to give the title compound.

According to the analysis of related databases, 17180-94-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SUNOVION PHARMACEUTICALS INC.; CAMPBELL, John, Emmerson; CAMPBELL, Una; HANANIA, Taleen, G.; SHAO, Liming; WO2013/119895; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 53135-24-3 ,Some common heterocyclic compound, 53135-24-3, molecular formula is C8H10N2O3, 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: Compound 17 c (2.90 g, 21 mmol) and diethyl (ethoxymethylidene)propanedioate (4.25 mL, 21 mmol) were dissolved in EtOH (30 mL). A solution of sodium ethoxide (20% in EtOH; 14.3 g, 42 mmol) was added to the solution dropwise at 0 C. After stirring at 80 C for 15 h, the reaction mixture was concentrated in vacuo. The residue was acidified with 1M HCl to pH 3. The precipitate was collected by filtration and washed with small amount of water. The product obtained (2.90 g, 13 mmol) was dissolved in POCl3 (9.6 g). After stirring at 100 C for 2 h, the reaction mixture was concentrated in vacuo. The residue was cooled to 0 C, neutralized with a saturated aqueous NaHCO3 solution to pH 7, and extracted with EtOAc. The extract was washed with brine, dried over Na2SO4, and concentrated in vacuo. A solution of the product obtained, furfurylamine (1.20 mL, 12.9 mmol), and diisopropylethylamine (2.26 mL, 12.9 mmol) in 2-propanol (10 mL) was stirred under reflux for 15 h. The reaction mixture was cooled to room temperature and concentrated in vacuo. The residue was diluted with a saturated aqueous NaHCO3 solution and extracted with EtOAc. The extract was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane/EtOAc=9:1 to 5:1). The product obtained was dissolved in 2M NaOH (15mL, 30mmol), EtOH (15mL), and THF (5mL). After stirring at room temperature for 15h, the mixture was acidified with 1M HCl to pH 3.0. The precipitate was collected by filtration and washed with water to give 18c as a colorless powder (3.30g, 57%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,53135-24-3, its application will become more common.

Reference:
Article; Imaeda, Yasuhiro; Tawada, Michiko; Suzuki, Shinkichi; Tomimoto, Masaki; Kondo, Mitsuyo; Tarui, Naoki; Sanada, Tsukasa; Kanagawa, Ray; Snell, Gyorgy; Behnke, Craig A.; Kubo, Keiji; Kuroita, Takanobu; Bioorganic and Medicinal Chemistry; vol. 24; 22; (2016); p. 5771 – 5780;,
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.74647-39-5, name is 4-Phenylpyrimidine-2-carboxylic acid, molecular formula is C11H8N2O2, molecular weight is 200.19, as common compound, the synthetic route is as follows.name: 4-Phenylpyrimidine-2-carboxylic acid

To a solution of 5-((6-methoxy-7-(3-morpholinopropoxy)quinolin-4-yl)oxy)pyridin- 2-amine (S?, 50 mg, 0.12 mmol), 4-phenylpyrimidine-2-carboxylic acid (19?, 35 mg, 0.17 mmol) in DMF (1 mL), DIEA (100 pL, 74 mg, 0.57 mmol) and HATU (140 mg, 0.37 mmol) were added. The reaction mixture was then allowed to stir at room temperature overnight, but a significant amount of the starting material 2-aminopyridine 5? was detected. Additional equivalents of reagents wre added and the reaction mixture was allowed to stir at room temperature until most of the starting 2-aminopyridine 5? was consumed. The reaction mixture was then diluted with water (20 ml) and extracted with DCM (3 x 10 mL) and the combined organic layer was dried (MgS()4) and concentrated to give a brown residue. Reverse phase chromatography provided 26 mg (36%) ofAr-(5-((6-methoxy-7-(3-morpholinopropoxy)quinolin- 4-yl)oxy)pyridin-2-yl)-4-phenylpyrimidine-2-carboxamide (4) as a white solid. NMR (CDJOD, 300 MHz) d 9.03 (d, J= 5.4 Hz, 1H), 8.72 (d, J = 6.7 Hz, 1H), 8.67 (dd, J= 9.1, 0.7 Hz, 1H), 8.52 (dd, J= 2.9, 0.7 Hz, 1H), 8.40 – 8.30 (m, 2H), 8.20 (d, J= 5.4 Hz, 1H), 7.99 (dd, J = 9.1, 2.9 Hz, i l l). 7.86 (s, 1H), 7.66 – 7.52 (m, 4H), 7.06 (d, J = 6.7 Hz, 1H), 4.43 (t, J= 5.5 Hz, 2H), 4.19 – 4 03 (br s, 21 1). 4.09 (s, 3H), 3.93 – 3.75 (m, 2H), 3.67 (d, J= 12.5 Hz, 2H), 3 49 (t, ./= 7 4 Hz, 2H), 3.28 – 3.13 (m, 2H), 2 45 (p, ,/= 6.4 Hz, 2H) MS m/e: 593 (M+H)7

At the same time, in my other blogs, there are other synthetic methods of this type of compound,74647-39-5, 4-Phenylpyrimidine-2-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; RIGEL PHARMACEUTICALS, INC.; DARWISH, Ihab; YU, Jiaxin; KOLLURI, Rao; HOLLAND, Sacha; (0 pag.)WO2019/231942; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 876-21-1, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 876-21-1 as follows.

(3) Synthesis of 4-amino-5-chloromethyl-2-ethylpyrimidine hydrochloride 4.59 g (0.03 mol) of 4-amino-2-ethyl-5-(hydroxymethyl)-pyrimidine was charged into a 100 ml flask, followed by 20 ml of dichloromethane, 20 ml of toluene and 0.1 ml of pyridine. 6.5 ml of thionyl chloride (0.28 mol) was dropped in slowly with cooling by ice bath. Then the reaction was stirred overnight. Solvent was removed and the residue was used for next step directly. 1H-NMR (400M, d-DMSO): 8.45 (s, 1H), 4.80 (s, 2H), 3.64 (s, 2H), 2.80 (dd, 2H, J=7.6, 14.8), 1.24 (t, 3H, J=7.6).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,876-21-1, its application will become more common.

Reference:
Patent; GUANGZHOU ORIGMOL FEED-ADDITIVE CO., LTD; Peng, Xianfeng; Qin, Zonghua; Liu, Qijun; US9096581; (2015); B2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 1480-66-6, 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 1480-66-6, name is 6-Chloro-2-(trifluoromethyl)pyrimidin-4-amine. This compound has unique chemical properties. The synthetic route is as follows.

Key Intermediate 5 (Int-5): (6-Chloro-2-trifluoromethyl-pyrimidin-4-yl)-[5-(3-ethoxy-benzenesulfonyl)-thiazol-2-yl]-amine; A mixture of 4-amino-6-chloro-2-trifluoromethyl-pyrimidine [(Inoue, S. et al, J. Org. Chem., 1961, 26, 4504) 185 mg, 0.94 mol] and NaH (60% dispersion in mineral oil, 40 mg, 1.0 mmol) in DMF (4.0 mL) was stirred, under Ar, at RT for 30 min. A solution of Intl-A (326 mg, 0.94 mmol) in DMF (2.0 mL) was added. The reaction mixture was stirred at RT for 30 min and was heated at 55 C. for 1 h. Additional NaH (60% dispersion in mineral oil, 20 mg, 0.05 mmol) was added, and the reaction mixture was heated at 55 C. overnight. Additional NaH (60% dispersion in mineral oil, 20 mg, 0.05 mmol) was added, and the reaction mixture was heated at 55 C. for 1 h. The reaction mixture was cooled to RT and partitioned between EtOAc (ca. 100 mL) and water (ca. 25 mL). The layers were separated and the organic phase was washed with saturated aqueous NaCl (1×100 mL), dried (Na2SO4), and concentrated under reduced pressure to give an oil. This oil was purified by flash chromatography, elution with 25-75% EtOAc in hexanes, to give Int-5 (182 mg, 42%) as a foam. LCMS (m/z): 465, 467 (M+H)+

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 1480-66-6, 6-Chloro-2-(trifluoromethyl)pyrimidin-4-amine.

Reference:
Patent; ICAGEN, INC.; US2007/197523; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 87253-62-1, 5,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-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, Computed Properties of C8H8N4O2, blongs to pyrimidines compound. Computed Properties of C8H8N4O2

General procedure: In 25ml RB flask to a solution of Compound 9 (200 mg) in dry DMF (5ml), EDCI (250 mg, 1.25eq) and DMAP (130 mg,1eq) were added followed by addition of Sulfonamide (1eq). RM was stirred at RT for 4hrs. Solvent from the reaction mixture was evaporated. To the residue water was added and acidified with 6N HCl, solid precipitated out. Solid was filtered and dried. Crude solid was purified by flash chromatography eluating with 4-8% MeOH/DCM as solvent system to give pure product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,87253-62-1, 5,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Article; Patil, Vikas; Kale, Manoj; Raichurkar, Anandkumar; Bhaskar, Brahatheeswaran; Prahlad, Dwarakanath; Balganesh, Meenakshi; Nandan, Santosh; Shahul Hameed; Bioorganic and Medicinal Chemistry Letters; vol. 24; 9; (2014); p. 2222 – 2225;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 14001-64-0, 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 14001-64-0, name is 4,6-Dimethyl-2-methylmercapyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

15.9 g (103 mmol) of 4,6-dimethyl-1-methylthiopyrimidine were introduced into 120 ml of dichloromethane and 110 ml of water.. chlorine gas was passed into saturation (yellow coloration) at 0 C. After the conversion was complete, excess chlorine was driven out with nitrogen, the aqueous phase was extracted with dichloromethane, and the collected organic phases were dried over magnesium sulfate.. The solution was concentrated, and the product (14 g, 73%) was crystallized by adding ether. Melting point: 79-80 C. 1H-NMR (270 MHz): 7.2 ppm (1H, s), 3.4 (3H, s), 2.6 (6H, s).

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 14001-64-0, 4,6-Dimethyl-2-methylmercapyrimidine.

Reference:
Patent; Abbott GmbH & Co., KG; US6670367; (2003); B1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 14001-69-5, 2-Methoxy-5-nitropyrimidine, 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

Example 40Synthesis of 4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-N-(2-methoxy-5-pyrimidinyl)-6-(4-morpholinyl)-1,3,5-triazin-2-amineThe compound was synthesized according to Method A.To a solution of sodium methoxide (0.090 g of sodium) in MeOH (12 mL) was added 0.486 g (3.03 mmol) of 2-chloro-5-nitropyrimidine, and the mixture was heated under reflux for 1 hr. After cooling, the mixture was concentrated in vacuo, extracted with EtOAc, and washed with water. The aqueous layer was extracted with CHCl3 and the combined organic layers were dried (Na2SO4), and concentrated, to give 0.347 g (75% yield) of 2-methoxy-5-nitropyrimidine as a yellow powder: 1H NMR (CDCl3) delta9.31 (s, 2H), 4.17 (s, 3H); LCMS (APCI+) m/z: 156 (MH+, 100%).To 0.342 g (2.20 mmol) of the above nitro compound in MeOH (20 mL) was added 0.30 g of 10% Pd/C and the mixture was stirred under hydrogen (25 in/Hg) for 18 hrs. The reaction mixture was filtered through celite, and concentrated, to give 0.274 g (100% yield) of 5-amino-2-methoxypyrimidine as a colorless oil: 1H NMR (DMSO-d6) delta 8.05 (s, 2H), 3.94 (s, 3H); LCMS (APCI+) m/z: 126 (MH+, 100%).To 0.274 g (2.19 mmol) of the above amino compound in THF (3 mL) was added 1.25 mL of NaHMDS (2 M solution in THF) and the mixture was stirred for 10 min. A solution of 0.31 g (0.78 mmol) of 1-[4-chloro-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-2-(difluoromethyl)-4-methoxy-1H-benzimidazole in THF (5 mL) was added and the resulting mixture was stirred for 90 min. The reaction mixture was neutralized with acetic acid, diluted with water, and extracted with EtOAc. The organic layer was washed with water and aq. NH3, dried, and concentrated. Recrystallization from EtOH/CH2Cl2 gave 0.098 g (26% yield) of 4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-N-(2-methoxy-5-pyrimidinyl)-6-(4-morpholinyl)-1,3,5-triazin-2-amine: mp 255-258 C.; 1H NMR (DMSO-d6) 810.07 (s, 1H), 8.88-8.74 (m, 2H), 8.15-7.42 (m, 3H), 6.97 (d, J=8.0 Hz, 1H), 3.98 (s, 3H), 3.93 (s, 3H), 3.82-3.72 (m, 8H); Anal. Calcd. for C21H21F2N6O3: C, 52.0; H, 4.4; N, 26.0. Found: C, 52.1; H, 4.5; N, 26.0%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,14001-69-5, 2-Methoxy-5-nitropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Pathway Therapeutics Limited; US2011/9405; (2011); 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. 206564-00-3, name is 4-(2-Furyl)pyrimidin-2-amine, the common compound, a new synthetic route is introduced below. COA of Formula: C8H7N3O

To a solution of 4-(2-furyl)-2-pyrimidinylamine (4.10 g, 25.4 mmol) in N,N-dimethylformamide (40 ml) was added N-bromosuccinimide (4.53 g, 25.5 mmol) at 2C, followed by stirring as it was. After 6 hours, the reaction mixture was diluted with an aqueous saturated sodium bicarbonate solution (240 ml). The mixture was ice-cooled, and then the crystals were collected by filtration and washed with water, to give the title compound (5.10 g, 84%) as a pale brown solid.1H NMR (400 MHz, DMSO-d6) delta ppm; 6.73 (1H, dd, J = 1.6, 3.6 Hz), 6.96 (2H, br s), 7.50 (1H, dd, J = 0.8, 3.6 Hz), 7.97 (1H, dd, J = 0.8, 1.6 Hz), 8.41 (1H, s).

The synthetic route of 206564-00-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Eisai Co., Ltd.; EP1439175; (2004); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia