Category: pyrimidines

Synthetic Route of 66522-06-3, Adding some certain compound to certain chemical reactions, such as: 66522-06-3, name is 4-(tert-Butyl)-2-chloropyrimidine,molecular formula is C8H11ClN2, 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 66522-06-3.

A mixture of 4-tert-butyl-2-chloropyrimidine (1.1 g, 6.4 mmol), 33% methylamine in ethanol (1 mL) in ethanol (4 mL) was placed in a sealed tube and heated to 60 C. for 3 h. The mixture was concentrated and the solid dissolved in chloroform. The organic layer was washed with water, dried over sodium sulfate, concentrated and chromatographed on silica gel with 30% EtOAc/Hexane. MS m/z 165 (MH)+.

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. 66522-06-3, 4-(tert-Butyl)-2-chloropyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Andersen, Denise Lyn; Chang, Catherine H.; Falsey, James R.; Frohn, Michael J.; Hong, Fang-Tsao; Liao, Hongyu; Liu, Longbin; Lopez, Patricia; Retz, Daniel Martin; Rishton, Gilbert M.; Rzasa, Robert M.; Siegmund, Aaron; Tadesse, Seifu; Tamayo, Nuria; Tegley, Christopher M.; US2006/69110; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 1250967-81-7, 2-Chloro-4-isopropoxypyrimidine, 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, 1250967-81-7, blongs to pyrimidines compound. HPLC of Formula: C7H9ClN2O

To a RT solution of Intermediate 2 (5 mg, 0.01 mmol) in n-BuOH (0.7 mL) were added 2-chloro-4-isopropoxypyrimidine (4 mg, 0.02 mmol) and iPr2NEt (9 pL, 0.05 mmol). The reaction was stirred at 180 C for 80 min, then was cooled to RT. THF (0.8 mL)/MeOH (0.4 mL)/H20 (0.4 mL) were added to the reaction mixture, followed by LiOH.H20 (3 mg, 0.07 mmol) at RT. The reaction was stirred at RT overnight, then was concentrated in vacuo and the residue was diluted with H20 (5 mL). The pH of the mixture was adjusted with aq. IN HC1 to ~5 and it was extracted with EtOAc (3 x 5 mL). The combined organic extracts were washed with brine (2 mL), dried (MgS04) and concentrated in vacuo. The crude product was purified by preparative LC/MS: Column: Waters XBridge C18, 19 x 200 mm, 5-mha particles; Guard Column: Waters XBridge C18, 19 x 10 mm, 5-pm particles; Mobile Phase A: 5:95 MeCN:H20 with 0.1% TFA; Mobile Phase B: 95:5 MeCN:H20 with 0.1% TFA; Gradient: 15-55% B over 20 min, then a 4-min hold at 100% B; Flow rate: 20 mL/min. Fractions containing the desired product were combined and concentrated via centrifugal evaporation to provide the title compound (6.5 mg, 8.7 pmol, 67 % yield). LCMS, [M+H]+ = 482.3. NMR (500 MHz, DMSO-de) d 8.42 (s, 1H), 8.06 (br s, 1H), 7.93 (s, 1H), 6.23 (br d, J=6.l Hz, 1H), 5.26 – 5.16 (m, 1H), 5.06 (br s, 2H), 4.84 – 4.77 (m, 1H), 3.92 (s, 3H), 2.68 – 2.60 (m, 1H), 2.42 (s, 3H), 2.06 – 1.44 (m, 8H), 1.22 (d, J=6.l Hz, 6H). hLPAi IC50 = 29 nM.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1250967-81-7, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; SHI, Yan; WANG, Ying; CHENG, Peter Tai Wah; LI, Jun; WALKER, Steven J.; (147 pag.)WO2019/126089; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 3270-97-1, Adding some certain compound to certain chemical reactions, such as: 3270-97-1, name is 2,4-Diamino-6-methoxypyrimidine,molecular formula is C5H8N4O, 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 3270-97-1.

EXAMPLE 3 Preparation of diethyl 6-methoxypyrimidine-2,4-dioxamate monohydrate: 2,4-Diamino-6-methoxypyrimidine (3.78 g) is dissolved in anhydrous pyridine (20 ml) and thereto is added dropwise ethyloxalyl chloride (9.83 g) under ice cooling, and the mixture is stirred at room temperature for one hour. To the reaction mixture is added water, and the mixture is extracted with ethyl acetate. The organic layer is washed with water and saturated aqueous sodium chloride, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting solid is recrystallized from water-ethanol to give title compound (8.8 g) having the following physical properties. m.p. 132-134 C. IR (KBr) nu: 3625, 3530, 3420, 3010, 1740, 1610, 1530, 1475, 1400, 1305, 1210, 1170, 1100, 1050, 1015, 970, 840 cm-1. NMR (DMSO-d6) delta: 11.30 (1H, s), 10.60 (1H, s), 7.03 (1H, s), 4.29 (4H, q), 3,87 (3H, s), 1.30 (3H, t), 1.25 (3H, t). Elementary analysis: Calcd.: C, 43.58; H, 5.06; N, 15.64 (%). Found: C, 43.75; H, 4.85; N, 15.89 (%).

According to the analysis of related databases, 3270-97-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Toyo Boseki Kabushiki Kaisha; US4729995; (1988); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 87253-62-1, 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. 87253-62-1, name is 5,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-carboxylic acid. A new synthetic method of this compound is introduced below.

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

Application of 69696-37-3 ,Some common heterocyclic compound, 69696-37-3, molecular formula is C6H7BrN2, 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.

A mixture of B16.5 (12 g, 64 mmol), bis(pinacolato)diboron (22.8 g, 89.6 mmol, 1.4 eq), KOAc (18.8 g, 192 mmol, 3.0 eq), and Pd(dppf)Cl2 (2.34 g, 3.2 mmol) in 200 mL of anhydrous dioxane was heated at 90 C and stirred for 4 h under N2. The solvent was removed under reduced pressure, the residue was diluted with 300 mL mixed solvent (PE:EtOAc = 4:1), filtered and concentrated. The crude product was purified by flash column chromatography (PE:EtOAc = 2:1 to 1:1) to give the title compound (10 g, 66%) as a yellow oil. LC-MS: [MH]+ = 235.

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. 69696-37-3, 5-Bromo-2,4-dimethylpyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; CHAN, Ho Man; FU, Xingnian; GU, Xiang-Ju Justin; HUANG, Ying; LI, Ling; MI, Yuan; QI, Wei; SENDZIK, Martin; SUN, Yongfeng; WANG, Long; YU, Zhengtian; ZHANG, Hailong; ZHANG, Ji Yue; ZHANG, Man; ZHANG, Qiong; ZHAO, Kehao; (193 pag.)WO2017/221092; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 206564-00-3 , The common heterocyclic compound, 206564-00-3, name is 4-(2-Furyl)pyrimidin-2-amine, molecular formula is C8H7N3O, 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: 4-p-Tolylpyrimidin-2-amine (3a) (1.0 equiv), N-chlorosuccinimide (1.1 equiv) and benzoyl peroxide (0.2 equiv) were dissolved in acetonitrile and stirred at 80 C for 6 h. The reaction mixture was cooled to room temperature, then the solvent was removed in vacuo. The crude product was purified by silica gel column with acetone/petroleum ether (v/v, 1:5) as eluent to obtain 4a. Using the same procedure described above for the other compounds exception of 6a-6c under a lower reaction temperature (40 C).

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

Reference:
Article; Chen, Wei; Li, Yuxin; Zhou, Yunyun; Ma, Yi; Li, Zhengming; Chinese Chemical Letters; vol. 30; 12; (2019); p. 2160 – 2162;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 53135-24-3, 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. 53135-24-3, name is Ethyl 2-methyl-6-oxo-1,6-dihydropyrimidine-5-carboxylate. A new synthetic method of this compound is introduced below.

ethyl 4-chloro-2-methylpyrimidine-5-carboxylate Phosphorus oxychloride (50 mL, 23.33 mmol) was added to ethyl 2-methyl-6-oxo-1,6-dihydropyrimidine-5-carboxylate (Intermediate 174, 4.25 g, 23.33 mmol). The insoluble mixture was refluxed for 30 minutes. The product was soluble in POCl3 where as the starting material was not. The excess POCl3 was removed under vacuum. The mixture was evaporated to dryness and redissolved in EtOAc (100 mL), and washed sequentially with water (75 mL) and saturated brine (75 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 10 to 30% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford ethyl 4-chloro-2-methylpyrimidine-5-carboxylate (2.70 g, 57.7%) as a colourless oil. 1H NMR (400.132 MHz, CDCl3) delta 1.42 (3H, t), 2.78 (3H, s), 4.44 (2H, q), 9.05 (1H, s) m/z (ESI+) (M+H)+=201; HPLC tR=2.17 min.

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:
Patent; AstraZeneca AB; US2009/264401; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 1480-66-6, 6-Chloro-2-(trifluoromethyl)pyrimidin-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 1480-66-6, blongs to pyrimidines compound. Product Details of 1480-66-6

6-Chloro-2-(trifluoromethyl)pyrimidin-4-amine (50 mg, 0.221 mmol) and potassium thioacetate (37.9 mg, 0.331 mmol) in Dioxane (3 ml) were heated in microwave (Temp. l00C, Hold time 10 min., Pressure 300, Power 150). After cooling, excess solvent was evaporated under reduced pressure. The reaction mixture was partitioned between ethyl acetate and water. The aqueous phase was extracted again with ethyl acetate. The organic solvent was then dried over MgS04 and evaporated under reduced pressure. The combined organic layers were dried over anhydrous MgS04 and evaporated under reduced pressure. The obtained residue was taken to the next step without further purification. LC/MS: m/z 196 (M+H)+.

The synthetic route of 1480-66-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HELMHOLTZ-ZENTRUM FUeR INFEKTIONSFORSCHUNG GMBH; AHMED, Ahmed S. A.; EMPTING, Martin; HAMED, Mostafa; HARTMANN, Rolf W.; HAUPENTHAL, Joerg; HASTERKAMP, Thomas; KAMAL, Ahmed A. M.; MAURER, Christine K.; ROeHRIG, Teresa; SCHUeTZ, Christian; YAHIAOUI, Samir; ZENDER, Michael; (128 pag.)WO2020/7938; (2020); 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. 1208087-83-5, name is 1-(2-Chloropyrimidin-4-yl)piperidine-4-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 1208087-83-5

To a suspension of the compound obtained in the previous step (8.87 g, 36.7 mmol) in dichloromethane (300 ml) were added Nu,Nu-diisopropylethyl amine (14.23 g, 1 10.1 mmol), 3,5- dimethoxyaniline (16.87 g, 1 10.1 mmol) and TBTU (17.68 g, 55.1 mmol). After stirring for 17h at room temperature the reaction mixture quenched by the addition of a saturated aqueous solution of sodiumbicarbonate and extracted with dicloromethane. The combined organic layers were dried over Na2S04 and evaporated under reduced pressure. The crude product was purified by normal phase chromatography, eluting with Heptane with 50% ethyl acetate to give 1 -(2-chloropyrimidin-4-yl)-N-(3,5-dimethoxyphenyl)piperidine-4-carboxamide (6.99 g) as a white solid

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, 1208087-83-5, 1-(2-Chloropyrimidin-4-yl)piperidine-4-carboxylic acid.

Reference:
Patent; MSD OSS B.V.; HUISMAN, Ines; VAN DER STELT, Marcelis; WIEDENHOF, Wouter; BAKER-GLENN, Charles, Anthony, Graham; BLACKABY, Wesley, Peter; TRIVEDI, Naimisha; WO2013/41457; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 392326-81-7, Adding some certain compound to certain chemical reactions, such as: 392326-81-7, name is 4-(4-Bromophenyl)pyrimidin-2-amine,molecular formula is C10H8BrN3, 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 392326-81-7.

To a slurry of 4-(4-bromo-phenyl)-pyrimidin-2-ylamine (300 mg, 1 mmol), bis(pinacolato)diborane (400 mg, 1.6 mmol), KOAc (330 mg, 3.3 mmol) in dioxane (7 mL) was added Pd(dppf)Cl2 (60 mg). The reaction mixture was heated to 100 C. for 2 h then cooled to RT. The solvent was removed. The residue was dissolved in DCM, washed with H2O, and dried (Na2SO4). Upon concentration, some of the product precipitated out and was collected to afford 90 mg of a mixture of 4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-pyrimidin-2-ylamine (70) and the corresponding boronic acid.

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. 392326-81-7, 4-(4-Bromophenyl)pyrimidin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Roche Palo Alto LLC; US2011/70190; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia