Tag: M.W:100-200

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

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

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

Electric Literature of 17321-93-6 ,Some common heterocyclic compound, 17321-93-6, molecular formula is C5H6BrN3, 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: The halo aryl (1.0 equiv) was dissolved in a mixture of water:dioxane (1:1). The boronic acid or ester(1.5 equiv) and potassium phosphate (5.0 equiv) were added. The solution was degassed byvacuum/argon cycles (10 times) before addition of PdCl2(PPh3)2 (10 molpercent) and further degassed (5times). The resulting mixture was stirred at 95 ¡ãC under argon atmosphere for 16-20 hours. Thereaction mixture was filtered through Celite and diluted with water (approx. 30 mL) before washingwith chloroform (3 x 30 mL). If not stated otherwise, the aqueous phase was concentrated underreduced pressure and applied to a C18 precolumn before purification on a 10g or 60 g C18 column witha gradient of acetonitrile in water (10-100percent) to yield the desired product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,17321-93-6, its application will become more common.

Reference:
Article; Akhter, Sundus; Lund, Bjarte Aarmo; Ismael, Aya; Langer, Manuel; Isaksson, Johan; Christopeit, Tony; Leiros, Hanna-Kirsti S.; Bayer, Annette; European Journal of Medicinal Chemistry; vol. 145; (2018); p. 634 – 648;,
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. 582313-57-3, name is 4-Chloro-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine, the common compound, a new synthetic route is introduced below. Recommanded Product: 582313-57-3

Into a 100-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 4-chloro-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine (700 mg, 4.08 mmol, 1.00 equiv) in tetrahydrofuran (40 mL), then compound 24a (1.528 g, 4.08 mmol, 1.00 equiv, J. Org. Chem. 2009, 74, 6819-6824) and triphenylphosphine (3.208 g, 12.24 mmol, 3.00 equiv) was added sequentially. This was followed by the addition of a solution of DEAD (2.131 g, 12.25 mmol, 3.00 equiv) in tetrahydrofuran (20 mL) dropwise with stirring at room temperature. The resulting solution was allowed to stir for 3 hours at room temperature,and then it was concentrated in vacuo. The resulting residue was purified using flash column chromatography on silica gel, eluting with ethyl acetate/petroleum ether (1:8) to provide 300 mg (14percent) of compound 24b as a white solid.

The synthetic route of 582313-57-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; VERMA, Vishal; ARASAPPAN, Ashok; NJOROGE, F. George; GIRIJAVALLABHAN, Vinay; BOGEN, Stephane, L.; DANG, Qun; OLSEN, David, B.; WO2013/9735; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 1780-26-3, 2-Methyl-4,6-dichloropyrimidine, 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-4,6-dichloropyrimidine, blongs to pyrimidines compound. Quality Control of 2-Methyl-4,6-dichloropyrimidine

The crude 2-methyl-4,6-dichloropyrimidine (41.8 g.; 256 mmol) was dissolved in dichloromethane (200 mL) and chilled to -78C in an inert atmosphere. Morpholine (48 g.; 550 mol) dissolved in dichloromethane (100 mL) was added slowly. The reaction was allowed to warm to room temperature while stirring overnight. The organic layer was washed with saturated ammonium chloride (2×100 mL), dried with sodium sulfate, and evaporated to give 2-methyl-4-chloro-6-morpholino-pyrimidine (48.5 g.; 227 mmol).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1780-26-3, 2-Methyl-4,6-dichloropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; SYNTA PHARMACEUTICALS CORP.; WO2006/124662; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 461-98-3 ,Some common heterocyclic compound, 461-98-3, molecular formula is C6H9N3, 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.

To a microwave tube was added 4-bromo-2-(2,6-dichlorophenyl)thiazolo[5,4-c]pyridine (60 mg, 0.17 mmol), 2,6-dimethylpyrimidin-4-amine (0.027 g, 0.22 mmol), Pd2(dba)3 (0.013 g, 0.017 mmol), XantPhos ((0.017 g, 0.034 mmol) and Cs2C03 (0.111 g, 0.34 mmol) in dioxane (3.0 mL). The mixture was degassed with N2 for 10 minutes and then irradiated in a microwave reactor at 160 C for 2 hours. After cooling to room temperature the solid was removed via filtration. The filtrate was concentrated under reduced pressure and the residue was purified with reverse phase column chromatography eluting with a 0-60% gradient of CH3CN in 0.5% NH4HC03 to give the desired product as a white solid (14 mg, 21% yield). ? NMR (500 MHz, CH3OH-??: delta 8.44 (d, J = 5.5 Hz, 1H), 7.71 (d, J = 5.5 Hz, 1H), 7.56-7.51 (m, 4H), 7.31 (s, 1H), 2.44 (s, 3H), 2.35 (s, 3H). LCMS (Method A): RT = 5.75 min, m/z: 402.0 [M+H+].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,461-98-3, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BLENCH, Toby; ELLWOOD, Charles; GOODACRE, Simon; LAI, Yingjie; LIANG, Jun; MACLEOD, Calum; MAGNUSON, Steven; TSUI, Vickie; WILLIAMS, Karen; ZHANG, Birong; WO2012/35039; (2012); 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.23906-13-0, name is 2-Hydrazinyl-4,6-dimethylpyrimidine, molecular formula is C6H10N4, molecular weight is 138.17, as common compound, the synthetic route is as follows.COA of Formula: C6H10N4

General procedure: To a solution of 0.2 g (3.6 mmol) of potassium hydroxide in 20 mL of ethanol was added successively 0.5 g (3.6 mmol) of hydrazine 5 and 3.6 mmol of an appropriate 3-aryl-1-phenyl-2-propen-1-one 4a-4d. The mixture was boiled for 2 h and cooled to room temperature. The separated precipitate was filtered off, washed with a minimal quantity of ethanol cooled to 5C, recrystallized from an appropriate solvent or mixture of solvents, and dried to a constant weight. Further physicochemical and spectral characteristics are listed for the products purified by crystallization.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,23906-13-0, 2-Hydrazinyl-4,6-dimethylpyrimidine, and friends who are interested can also refer to it.

Reference:
Article; Erkin; Yuzikhin; Krutikov; Russian Journal of Organic Chemistry; vol. 52; 8; (2016); p. 1173 – 1178; Zh. Org. Khim.; vol. 52; 8; (2016); p. 1181 – 1185;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 23945-44-0, 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. 23945-44-0, name is 2,4-Dihydroxypyrimidine-5-carboxylic acid. A new synthetic method of this compound is introduced below.

Example 16 2,4-DICHLOROPYRIMIDINE-5-CARBONYL CHLORIDE The title compound was prepared as described in the literature (Smith and Christensen, J. Org. Chem. 20:829, 1955) starting from 2,4-dihydroxypyrimidine-5-carboxylic acid. The compound was obtained by distillation; b.p. 90-100 C. (1.5 mm/Hg) in a yield of 46%; 1 H-NMR (CDCl3) delta 9.29.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,23945-44-0, 2,4-Dihydroxypyrimidine-5-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; Signal Pharmaceuticals, Inc.; US5811428; (1998); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 1005-38-5, Adding some certain compound to certain chemical reactions, such as: 1005-38-5, name is 4-Amino-6-chloro-2-(methylthio)pyrimidine,molecular formula is C5H6ClN3S, 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 1005-38-5.

Example 9A; 7-Chloro-5-(methylthio)imidazo[1,2-c]pyrimidine 75 g (427 mmol) of 4-amino-6-chloro-2-(methylthio)pyrimidine are dissolved in 3000 ml of dioxane and 750 ml of water. 101.05 g (597.81 mmol) of bromoacetaldehyde dimethyl acetal are added, and the mixture is heated under reflux for 24 h. After the reaction is complete, the dioxane is removed in vacuo and the aqueous suspension is suspended in THF, filtered with suction and washed with some THF. Drying of the solid at 40 C. under high vacuum results in 56.5 g (66% of theory) of the product.MS (ES+): m/z=200 (M+H)+.1H-NMR (400 MHz, DMSO-d6): delta=8.12 (s, 1H), 7.97 (s, 1H), 7.77 (s, 1H), 2.80 (s, 3H).

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. 1005-38-5, 4-Amino-6-chloro-2-(methylthio)pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; US2010/113441; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia