Day: April 28, 2021

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. 1005-38-5, name is 4-Amino-6-chloro-2-(methylthio)pyrimidine, the common compound, a new synthetic route is introduced below. COA of Formula: C5H6ClN3S

[00549] To a stirred solution of 6-chloro-2-(methylsulfanyL)pyrimidin-4-amine (1.5 g, 8.54 mmol) in dioxane (4 mL) was added chloroacetaldehyde (50%, 1.63 mL, 12.8 mmol) and stirred at 95 C overnight. The reaction mixture was cooled in an ice bath and the resulting precipitate filtered and washed with dioxane to afford the title compound (1.41 g, 70%) as a colourless powder. [00550] Method A: LC-MS m/z = 199.8 [M + H]+; RT = 0.93 min

The synthetic route of 1005-38-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; QUARTET MEDICINE, INC.; ECOLE POLYTECHNIQUE FEDERALE DE LAUSANNE (EPFL); TEBBE, Mark, Joseph; ATTON, Holly, Victoria; AVERY, Craig; BROMIDGE, Steven, Mark; KERRY, Mark; KOTEY, Adrian, Kotei; MONCK, Nathaniel, J.; MENICONI, Mirco; RIDGILL, Mark, Peter; TYE, Heather; SAIAH, Eddine; JOHNSSON, Kai, Peter; GORSKA, Katarzyna, Irena; PENG, Hairuo; MCCALL, John, Michael; (356 pag.)WO2017/59191; (2017); 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. 5734-66-7, name is 2-Amino-6-ethylpyrimidin-4-ol. This compound has unique chemical properties. The synthetic route is as follows. category: pyrimidines

A. 2-Amino-5-bromo-6-ethyl-4-pyrimidinol By bromination of 6-ethyl-isocytosine with N-bromosuccinimide To a faintly warm solution of 1.112 g. (8.0 millimoles) of 6-ethyl-isocytosine in 16 ml. of glacial acetic acid is added 1.424 g. (8.0 millimoles) of N-bromosuccinimide. The reaction flask is closed with a drying tube, and the mixture heated briefly on a steam bath, with occasional swirling, until solution is complete. The solution is heated on a steam bath for 1 hour, then allowed to cool spontaneously. The cooled solution is seeded with crystals from an earlier run and kept at ambient temperature for several days. The resulting crystals are collected, washed first with cool glacial acetic acid then with anhydrous ether. The material is dried, first in air then in vacuo at 76C. for several hours. The crude material, 960 mg., is crystallized from about 20 ml. of 50% aqueous acetic acid, using decolorizing charcoal. The product is collected, washed successively with cold 50% aqueous acetic acid, cold 95% ethanol and anhydrous ether. The pure material, after brief airdrying, is dried in vacuo at ca. 80C. There is thus obtained 660 mg. of 2-amino-5-bromo-6-ethyl-4-pyrimidinol which melts at 225 to 225.5 centigrade, has a lambdamax0.1N NaOH 230.5 nm. (epsilon8,200); 283 nm. (epsilon7,200) and the infrared absorption below. Nh/oh, 3380, 3320, 3130, 2720; c=o/c=n/c=c, 1675, 1640, 1610, 1565; c–o/c–n other, 1340, 1310, 1215, 1060, 1005 cm-1. Analysis Calcd. for: C6 H8 BrN3 O: C, 33.05; H, 3.17; Br, 36.65; N, 19.27.Found: C, 32.98; H, 3.63; Br, 36.75; N, 18.81.

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, 5734-66-7, 2-Amino-6-ethylpyrimidin-4-ol.

Reference:
Patent; The Upjohn Company; US3956302; (1976); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 14160-93-1, 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. 14160-93-1, name is 4-Amino-6-chloropyrimidine-5-carbaldehyde. A new synthetic method of this compound is introduced below.

To a mixture of trimethoxybenzylamine (469 mg, 2.38 mmol, 1.0 equiv., HCl salt free based prior to use), 4 angstrom molecular sieves (290 mg), and aldehyde 15.2 (375 mg, 2.38 mmol, 1.0 equiv.) in dichloromethane (5 mL) was added acetic acid (0.14 mL, 2.43 mmol, 1.02 equiv.). After stirring for 3 hr at RT, sodium triacetoxyborohydride (757 mg, 3.57 mmol, 1.5 equiv.) was added and the reaction mixture was stirred at RT for 21.5 hr. The reaction mixture was diluted with dichloromethane (20 mL) and aqueous saturated NaHCO3 (20 mL). The aqueous layer was extracted with dichloromethane (4¡Á20 mL), and the combined organic extracts were washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The resultant crude residue and Boc2O (524 mg, 2.38 mmol, 1 equiv.) were dissolved in THF (10 mL), and pyridine (0.59 mL, 5.95 mmol, 2.5 equiv.) was added. After stirring at RT for 16.5 hr, the reaction mixture was diluted with water (25 mL), EtOAc (25 mL), and 1 N aqueous HCl (25 mL). The aqueous layer was extracted with EtOAc (4¡Á30 mL). The combined organic extracts were washed with water (50 mL), 1 N aqueous HCl (50 mL), and brine (50 mL), dried over anhydrous sodium sulfate, and concentrated. Purification by flash column chromatography (50-60-66% EtOAc/hexanes) afforded compound 15.3 (403 mg, 39% over 2 steps) as a beige foam. LCMS: m/z: 439 [M+1]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,14160-93-1, 4-Amino-6-chloropyrimidine-5-carbaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; Sunesis Pharmaceuticals, Inc.; US2009/36419; (2009); 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.22536-66-9, name is 2-Chloropyrimidine-4-carboxamide, molecular formula is C5H4ClN3O, molecular weight is 157.5578, as common compound, the synthetic route is as follows.HPLC of Formula: C5H4ClN3O

To a 5 mL vial containing a stir bar, 3-(2-aminopyrimidin-5-yl)-6-cyclobutyl-2-fluorophenol (80 mg, 0.31 mmol) and 2-chloropyrimidine (41 mg, 0.34 mmol) were added Cs2CO3 (203 mg, 0.62 mmol) and DMSO (0.8 mL). The resultant mixture was stirred at 120 Celsius for approximately 1 hour via microwave irradiation. The reaction mixture was cooled to room temperature before passing the mixture through a syringe filter and subjecting the filtrate to FCC to afford the title compound (81 mg, 78%). The title compound was prepared using conditions similar to those described in Example 160 heating at 80 Celsius via microwave radiation for 2 hours and using 2-chloropyrimidine-4-carboxamide. MS (ESI): mass calcd. for C19H17FN6O2, 380.14; m/z found, 381.0 [M+H]+. 1H NMR (400 MHz, DMSO-d6) delta 8.81 (d, J=4.9, 1H), 8.44 (s, 2H), 8.21 (s, 1H), 7.98 (s, 1H), 7.77 (d, J=4.9, 1H), 7.52-7.42 (m, 1H), 7.30 (d, J=8.2, 1H), 6.89 (s, 2H), 3.63-3.51 (m, 1H), 2.15-2.00 (m, 4H), 1.99-1.84 (m, 1H), 1.81-1.68 (m, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,22536-66-9, 2-Chloropyrimidine-4-carboxamide, and friends who are interested can also refer to it.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; Eccles, Wendy; Fitzgerald, Anne E.; Hack, Michael D.; Hawryluk, Natalie A.; Jones, William M.; Keith, John M.; Krawczuk, Paul; Lebsack, Alec D.; Liu, Jing; Mani, Neelakandha S.; McClure, Kelly J.; Meduna, Steven P.; Rosen, Mark D.; US2014/221310; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 5399-92-8, 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. 5399-92-8, name is 4-Chloro-1H-pyrazolo[3,4-d]pyrimidine. A new synthetic method of this compound is introduced below.

Slowly add a solution of DIPEA (63g, 0.488mol, Chinese name: N, N-diisopropylethylamine) in THF (50mL) at -20 C to SM (50g, 0.324mol) and 2- (trimethyl In a mixed solution of silyl) ethoxymethyl chloride (62 g, 0.39 mol, SEMCl) in DMF (50 mL) and THF (200 mL), after stirring at -20 C for 3 hours, water was added to quench it, and ethyl acetate Ester extraction, drying the organic phase, filtering, and concentrating to obtain the crude product, which was purified by flash column using petroleum ether and ethyl acetate (v / v = 1/1) as eluent to obtain pale yellow oil A-1 (45g, 0.158 mol, yield: 32.6%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,5399-92-8, 4-Chloro-1H-pyrazolo[3,4-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Hangzhou Ao Jin Bio-pharmaceutical Co., Ltd.; Yin Jianming; (18 pag.)CN110446713; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 130049-82-0, 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 130049-82-0, name is 3-(2-Chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidine-4-one. This compound has unique chemical properties. The synthetic route is as follows.

Example 36 3-(2-(4-(benzo[b]thiophen-4-yl)piperidin-1-yl)ethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one 3-(2-chloroethyl)-9-hydroxy-2-methyl-6,7, 8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-on e 10-a (133 mg, 0.55 mmol), the product of Reference Example 31 (120 mg, 0.55 mmol), potassium carbonate (229 mg, 1.65 mmol), potassium iodide (92 mg, 0.55 mmol) and acetonitrile (5 ml) were added to the flask. The mixture was stirred at reflux for 12 hours, concentrated, and the residue was purified by column chromatography to obtain a white solid (115 mg, yield: 49%). 1H-NMR (400 Hz, DMSO-d6): delta ppm 7.84 (d, 1H), 7.76 (d, 1H), 7.62 (d, 1H), 7.33 (t, 1H), 7.26 (d, 1H), 5.71 (d, 1H), 4.45 (q, 1H), 3.91 (m, 1H), 3.68 (m, 1H), 3.08 (m, 3H), 2.65 (m, 2H), 2.41 (t, 2H), 2.28 (s, 3H), 2.21 (t, 2H), 2.06-1.70 (m, 8H). ESI-MS (m/z): 424.4 [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 130049-82-0, 3-(2-Chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidine-4-one.

Reference:
Patent; SHANGHAI INSTITUTE OF MATERIA MEDICA, CHINESE ACADEMY OF SCIENCES; SUZHOU VIGONVITA LIFE SCIENCES CO., LTD.; TOPHARMAN SHANDONG CO., LTD.; JIANG, Hualiang; WANG, Zhen; LI, Jianfeng; ZHANG, Rongxia; HE, Yang; LIU, Yongjian; BI, Minghao; LIU, Zheng; TIAN, Guanghui; CHEN, Weiming; YANG, Feipu; WU, Chunhui; WANG, Yu; JIANG, Xiangrui; YIN, Jingjing; WANG, Guan; SHEN, Jingshan; (70 pag.)US2017/158680; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 304693-64-9, Ethyl 2-(trifluoromethyl)pyrimidine-5-carboxylate, 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, Application In Synthesis of Ethyl 2-(trifluoromethyl)pyrimidine-5-carboxylate, blongs to pyrimidines compound. Application In Synthesis of Ethyl 2-(trifluoromethyl)pyrimidine-5-carboxylate

To a solution of ethyl 2-(trifluoromethyl)pyrimidine-5-carboxylate (56.8 g, 252.8 mmol) dissolved in THF (500 mL) was added 1M aq. LiCH (380 mL, 379.3 mmol). The reaction mixture was stirred at RT for 16 h, concentrated under vacuum toremove the organic solvent and the remaining aqueous acidified to pH 1 with conc.HCI. The resultant precipitate was collected by vacuum filtration to afford 44.4(91 % yield) of the title compound as off-white powder.1H NMR (500 MHz, DMSO-d6): 6 [ppm] 9.44 (5, 2H).LCMS (Analytical Method A) Rt = 0.81 mm, MS (ESineg): m/z = 190.9 (M)-.

The synthetic route of 304693-64-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EVOTEC AG; DAVENPORT, Adam James; BRAEUER, Nico; FISCHER, Oliver Martin; ROTGERI, Andrea; ROTTMANN, Antje; NEAGOE, Ioana; NAGEL, Jens; GODINHO-COELHO, Anne-Marie; (703 pag.)WO2016/91776; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 24415-66-5, 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine, 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, Safety of 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine, blongs to pyrimidines compound. Safety of 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine

Take about 1 mmol of 7-chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine and about 3 mmol1-(4-fluorobenzyl)-1H-indole-5-carbonitrile and added to a 10 mL microwave reaction tube.Adding 2 mL of hexafluoroisopropanol solvent and about 0.1 mmol of bistrifluoromethanesulfonimide catalyst, sealing and stirring to 100 C and reacting for about 6 h;Then, the reaction system was monitored by TLC. After the reaction system was cooled to room temperature, it was separated and purified by column chromatography to obtain pure compound e1.The compound e1 is a yellow solid, and the yield is about 86% by detection.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,24415-66-5, 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Zhengzhou University; Liu Hongmin; Yu Bin; Zheng Yichao; Yuan Shuo; Shen Dandan; (27 pag.)CN109020976; (2018); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 20090-58-8, 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.20090-58-8, name is 4-Chloro-5-methylpyrimidin-2-amine, molecular formula is C5H6ClN3, molecular weight is 143.5742, as common compound, the synthetic route is as follows.

To a solution of 4-chloro-5-methylpyrimidin-2-amine (25 mg, 0.17 mmol) in Dioxane (0.5 ml) were added 2,2-dimethylpropane-l,3-diol (19.95 mg, 0.19 mmol) and NaH 60% dispersion in mineral oil (13.93 mg, 0.34 mmol) and the resulting mixture was stirred at 60 C overnight. The mixture was quenched with 6N HCl (0.058 ml, 0.34 mmol) and the volatiles were removed under reduced pressure. The residue was purified by mass-triggered preparative HPLC (Mobile phase: A = 0.1% TFA/H2O, B = 0.1% TFA/MeCN; Gradient: B = 10 – 50%; 12 min; Column: C18) to give 3-((2-amino-5-methylpyrimidin-4-yl)oxy)-2,2-dimethylpropan-l-ol (5.2 mg, 0.025 mmol, 14% yield) as a white solid. MS (ES+) C10H17N3O2 requires: 211, found: 212 [M+H]+. NMR (600 MHz, de-DMSO) delta: 8.04 (brs, 2H), 7.95 (s, 1H), 4.68 (brs, 1H), 4.13 (brs, 2H), 3.26 (s, 2H), 1.97 (s, 3H), 0.92 (s, 6H).

Statistics shows that 20090-58-8 is playing an increasingly important role. we look forward to future research findings about 4-Chloro-5-methylpyrimidin-2-amine.

Reference:
Patent; BOARD OF REGENTS, UNIVERSITY OF TEXAS SYSTEM; LEWIS, Richard, Thomas; JONES, Philip; PETROCCHI, Alessia; REYNA, Naphtali; HAMILTON, Matthew, Michael; LEO, Elisabetta; (74 pag.)WO2016/145383; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 5466-43-3, 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 5466-43-3, name is 2,4-Dichloro-6,7-dihydro-5H-cyclopenta[d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a solution of 2,4-dichlorofuro[3,2-d]pyrimidine (la) (0.71 g, 3.74 mmol; CAS 956034- 07-4) in 2-Propanol (20 mL) was added DIPEA (1.63 mL, 9.36 mmol), 1-methyl-1H-imidazol-4-amine hydrochloride (0.5 g, 3.74 mmol) and heated at reflux for 24 h. The reaction mixture was concentrated in vacuum to dryness and the residue obtained was triturated with water. The solid obtained was collected by filtration and dried in vacuum to afford 2-chloro-N-(l-methyl-lH-imidazol-4-yl)furo[3,2-d]pyrimidin-4-amine (lb) (550 mg,59 % yield) as brown solid; NMR (300 MHz, DMSO-^) delta 10.89 (s, 1H, D20exchangeable), 8.35 (d, J = 2.1 Hz, 1H), 7.52 (d, J = 1.6 Hz, 1H), 7.39 (d, J = 1.3 Hz, 1H), 7.03 (d, J = 2.1 Hz, 1H), 3.71 (s, 3H); MS (ES+): 250.3 (M+l), 272.3, 274.3 (M+Na), (ES-): 248.2 (M-l).

According to the analysis of related databases, 5466-43-3, the application of this compound in the production field has become more and more popular.

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