Pyrimidines

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.504-17-6, name is 4,6-Dihydroxy-2-mercaptopyrimidine, molecular formula is C4H4N2O2S, molecular weight is 144.1518, as common compound, the synthetic route is as follows.COA of Formula: C4H4N2O2S

General procedure: A mixture of an isatin (1mmol), molononitrile (1mmol), CH activatedacid (1mmol), and [C4(DABCO)2]·2OH(2mol%) inwater (3mL)was stirred at 80 C. The reaction progress was monitored by TLC [eluent:n-hexane:EtOAc (9:2)] (It is important to that by beginning of thereaction the products were precipitated in the reaction medium).After completion of the reaction, the mixture was cooled to room temperature and the solid product was filtered, washed with cold distilledwater (2 mL) to obtain essentially pure products. The solid productswere recrystallized from ethanol if necessary.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,504-17-6, 4,6-Dihydroxy-2-mercaptopyrimidine, and friends who are interested can also refer to it.

Reference:
Article; Goli-Jolodar, Omid; Shirini, Farhad; Seddighi, Mohadeseh; Journal of Molecular Liquids; vol. 224; (2016); p. 1092 – 1101;,
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Adding a certain compound to certain chemical reactions, such as: 19178-25-7, Pyrido[3,4-d]pyrimidin-4(3H)-one, 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, 19178-25-7, blongs to pyrimidines compound. SDS of cas: 19178-25-7

A suspension of pyrido[3,4-d]pyrimidin-4-ol (33)(1.47 g, 10 mmol) in thionylchloride (30 ml) and dimethylformamide (50 mul, cat.) was heated to reflx (90 C.) for 1 hour. The mixture was then cooled and concentrated in vacuo and then diluted with CH2Cl2 (50 ml) which caused a suspension to form. The solid was removed by filtration, washed with cold CH2Cl2 (10 ml) to give the title compound (1.65 g, 99.4%) in sufficiently pure form to be used without any further purification. m/z (LC-MS, ESP): 166 [M+H]+, R/T=2.82 mins.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,19178-25-7, its application will become more common.

Reference:
Patent; Kudos Pharmaceuticals Ltd; US2006/199804; (2006); A1;,
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Related Products of 1032452-86-0, 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 1032452-86-0, name is 3-(2-Chloropyrimidin-4-yl)-1-methyl-1H-indole. This compound has unique chemical properties. The synthetic route is as follows.

4-Methylbenzenesulfonic acid hydrate (8.7 g) was added in one portion to 3-(2-chloropyrimidin-4-yl)-1-methylthdole (9.3 g) and 4-fluoro-2-methoxy-5-nitroaniline (7.1 g) in n-butanol (200 mL). The resulting mixture was stirred at reflux for 1 h. The mixture was cooled to room temperature. The precipitate was collected by filtration, washed with n-butanol (50 mL), and dried under vacuum to afford N-(4-fluoro-2-methoxy-5-nitrophenyl)-4-(1-methylindol-3-yl)pyrimidin-2-amine as a yellow solid (Compound 5, 15.5 g).

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 1032452-86-0, 3-(2-Chloropyrimidin-4-yl)-1-methyl-1H-indole.

Reference:
Patent; X-Cutag Therapeutics, Inc.; CHENG, Changfu; WEN, Shuhao; LI, Hui Joyce; (30 pag.)US2019/169171; (2019); A1;,
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Pyrimidine – Wikipedia

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. 5305-45-3, name is 4,6-Dichloropyrimidine-5-carbonitrile. A new synthetic method of this compound is introduced below., category: pyrimidines

A mixture of (S)-1-(7-fluoro-2-(pyridin-2-yl)quinolin-3-yl)ethanamine (85 mg, 0.32 mmol), 4,6-dichloro-5-cyanopyrimidine (55 mg, 0.32 mmol, 1.0 eq) and N,N-diisopropylethylamine (68 mul, 0.38 mmol, 1.2 eq) in THF (3 mL) was stirred at rt for 30 min before heating to 50 C. After 4 h, the mixture was concentrated and purified by column chromatography (EtOAc/1/1) to give a white solid, which was treated with saturated NH3 in dioxane (3 mL) in sealed tube at 110 C. overnight. The reaction mixture was concentrated and purified by reverse phase HPLC (MeCN/H2O/0.1% TFA) and lyophilized to give a white powder 4-amino-6-((S)-1-(7-fluoro-2-(pyridin-2-yl)quinolin-3-yl)ethylamino)pyrimidine-5-carbonitrile (19 mg, 15%). 1H NMR (500 MHz, CD3OD) delta ppm 1.78 (d, J=6.85 Hz, 3H) 5.82 (q, J=6.85 Hz, 1H) 7.71 (td, J=8.80, 2.45 Hz, 1H) 7.89 (dd, J=9.66, 2.32 Hz, 1H) 8.10 (ddd, J=7.83, 5.62, 0.98 Hz, 1H) 8.19 (s, 1H) 8.27 (dd, J=9.05, 5.87 Hz, 1H) 8.45 (d, J=7.83 Hz, 1H) 8.63 (td, J=7.95, 1.47 Hz, 1H) 8.94 (s, 1H) 9.03-9.09 (m, 1H). Mass Spectrum (ESI) m/e=386 (M+1).

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, 5305-45-3, 4,6-Dichloropyrimidine-5-carbonitrile.

Reference:
Patent; Amgen Inc.; Bui, Minna; Cushing, Timothy David; Gonzalez Lopez De Turiso, Felix; Hao, Xiaolin; Lucas, Brian; US2013/267524; (2013); A1;,
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Pyrimidine – Wikipedia

Reference of 26830-94-4, 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. 26830-94-4, name is 2,6-Dichloropyrimidine-4-carbonyl chloride, molecular formula is C5HCl3N2O, 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.

To a solution of Compound 2 (26.13 g, 123.6 mmol) in Et20 (500 mL) was added a mixture of 0.5M NH3 in dioxane (250 mL, 125 mmol) and DIPEA (22 mL, 126 mmol) dropwise over 50 mm. After stirring at RT overnight the reaction mixture was concentrated in vacuo to give a residue that was purified by flash chromatography (5i02, 10-50% EtOAc/hexanes). The product obtained was triturated with 10 mL 10% EtOAc/hexanes andfiltered to give Compound 3 as an orange crystalline solid (9.74 g). Yield 41%1H NMR (400 MHz, DMSO-d6): oe 8.40 (br s, 1H), 8.16 (br s, 1H), 8.10 (s, 1H); LC/MS: nz/z= 192.2 [M+Hf (Calc: 191.4).

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 26830-94-4, 2,6-Dichloropyrimidine-4-carbonyl chloride.

Reference:
Patent; PURDUE PHARMA L.P.; TAFESSE, Laykea; PARK, Jae, Hyun; WO2015/123398; (2015); A1;,
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Pyrimidine – Wikipedia

Synthetic Route of 1088994-22-2 ,Some common heterocyclic compound, 1088994-22-2, molecular formula is C12H10N2O2, 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: To a solution of 5-methyl-2-(pyrimidin-2-yl)benzoic acid(0.040 g, 0.19 mmol) in CHCl3 (1.5 mL) were added DIPEA(0.092 ml, 0.53 mmol), 43d (0.037 g, 0.15 mmol) and a solution of1-propanephosphonic acid cyclic anhydride (T3P, 1.7 mol/L inEtOAc, 0.30 ml, 0.52 mmol) at room temperature. After this mixturewas stirred at 60 C for 5 h, water was added, and the mixturewas extracted with CHCl3. The organic layer was washed withbrine, dried over Na2SO4, filtered, and concentrated under reducedpressure. The resulting residue was purified by preparative HPLC toobtain the titled compound 12 as a colorless amorphous (0.024 g,36% yield). HRMS (ESI/APCI dual) for C24H24FN6O2 [M+H]+, calcd:447.1939, found: 447.1923; LC-MS t = 0.87 min, [M+H]+ = 447.Please see the Supplementary data for pictures of 500 MHz 1Hand 125 MHz 13C NMR spectra in CDCl3 at 25 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1088994-22-2, its application will become more common.

Reference:
Article; Futamura, Aya; Nozawa, Dai; Araki, Yuko; Tamura, Yunoshin; Tokura, Seiken; Kawamoto, Hiroshi; Tokumaru, Yuichi; Kakihara, Sora; Aoki, Takeshi; Ohtake, Norikazu; Bioorganic and Medicinal Chemistry; vol. 25; 20; (2017); p. 5203 – 5215;,
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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 7752-78-5, name is 5-Bromo-2-methylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 7752-78-5

c) 1-Isopropyl-3,3-dimethyl-6-(2-methylpyrimidin-5-yl)indolin-2-one Through a suspension of 1 -isopropyl-3 ,3 -dimethyl-6-(4,4,5 ,5 -tetramethyl- 1,3 ,2-dioxaborolan-2-yl)indolin-2-one (220 mg, 668 imol), 5-bromo-2-methylpyrimidine (139 mg, 802 imol) and 2Maqueous Na2CO3 solution (668 tl, 1.34 mmol) in dioxane (3.0 ml) was bubbled argon for 5 minutes. [1,1 ?-Bis(diphenylphosphino)ferroceneldichloropalladium(II), complex with dichloromethane (1:1) (27.3 mg, 33.4 imol) was added and argon was bubbled through again for 5 minutes. The reaction mixture was heated to 110 °C for 20 hous. The solvent was evaporated and the residue was purified by silica gel chromatography using EtOAc/ heptane as eluentfollowed by amino silica gel chromatography using EtOAc/ heptane as eluent. The titlecompound was obtained as off-white solid (115 mg).MS ESI (m/z): 296.3 [(M+H)j.1H NMR (CDC13, 300 MHz): oe = 8.83 (s, 2H), 7.32 (d, J=7.7 Hz, 1H), 7.23 – 7.15 (m, 1H), 7.12(d, J=1.4 Hz, 1H), 4.69 (spt, J=7.1 Hz, 1H), 2.81 (s, 3H), 1.52 (d, J=7.1 Hz, 6H), 1.39 (s, 6H).

With the rapid development of chemical substances, we look forward to future research findings about 7752-78-5.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BRUNNER, Daniela; HILPERT, Hans; KOLCZEWSKI, Sabine; LIMBERG, Anja; MALBERG, Jessica; PRINSSEN, Eric; RIEMER, Claus; SHANKAR, Bavani G.; STOLL, Theodor; WO2014/202493; (2014); A1;,
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Pyrimidine – Wikipedia

Reference of 5604-46-6 ,Some common heterocyclic compound, 5604-46-6, molecular formula is C5H3Cl2N3O, 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.

PRODUCTION EXAMPLE 5, METHOD A-5 2-Amino-6-chloro-4-[[(3-(2-phenylethyl)-1-hydroxymethyl-1-cyclobutyl)methyl]amino]-5-formylpyrimidine (compound No. 71) 1-Hydroxymethyl-3-(2-phenylethyl)-1-cyclobutylmethylamine (3.51 g, 0.016 mol) was dissolved in ethanol (60 ml), and 2-amino-4,6-dichloro-5-formylpyrimidine (3.07 g, 0.016 mol) and triethylamine (6 ml) were added, which was followed by reflux for 2 hours. The solvent was distilled away under reduced pressure and chloroform was added to the residue. The mixture was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled away under reduced pressure and the residue was purified by silica gel column chromatography (chloroform, later chloroform_methanol=100:1) to give pale-yellow crystals (2.4 g, 40.0%), m.p. 130-137 C. (ether).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5604-46-6, its application will become more common.

Reference:
Patent; Nippon Shoji Kaisha Ltd.; US6080750; (2000); A;,
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Pyrimidine – Wikipedia

Application of 95928-49-7, 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. 95928-49-7, name is Ethyl 2-hydroxypyrimidine-5-carboxylate, molecular formula is C7H8N2O3, 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.

Step 4:Ethyl 2-chloropyrimidine-5-carboxylateEthyl 2-oxo-1,2-dihydropyrimidine-5-carboxylate (100 g, 0.59 mol) was slurried in POCl3 (600 mL) and cooled in an ice/water bath.The reaction mixture was heated to reflux temperature (oil-bath, T=117° C.) for 2 h.The light-brown colored homogeneous reaction mixture was cooled and the excess of POCl3 was removed by vacuum distillation.The semisolid brown residue was cooled (ice-water bath), toluene (400 mL) and a mixture of water (400 mL) and ice (200 g) were added.The mixture was stirred for 2 h and filtered.The organic phase was separated, dried and concentrated to dryness on a rotary evaporator.The dark yellow residue was purified by flash chromatography (SiO2, heptane/ethyl acetate 9/1) to afford the title compound.1H NMR (500 MHz, DMSO-d6): delta 9.18 (s, 2H); 4.38 (q, 2H); 1.34 (t, 3H).

According to the analysis of related databases, 95928-49-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Leclerc, Jean-Philippe; Li, Chun Sing; Ramtohul, Yeeman K.; US2011/152295; (2011); A1;,
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Pyrimidine – Wikipedia

Related Products of 13627-49-1, 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 13627-49-1, name is 2-Methylpyrimidine-4-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows.

2-methylpyrimidine-4-carboxylic acid (250 mg, 1.810 mmol) was slurried in N,N,Dimethylformamide (dry) (3 ml). DIPEA (0.378 ml, 2.172 mmol) was added followed by HATU (757 mg, 1.991 mmol). After 15 mins 2-chloroaniline (0.191 ml, 1.810 mmol) was added to the brown suspension and the resulting reaction mixture stirred further at room temperature overnight. The reaction mixture was evaporated (55C to half volume (~4ml). This mixture was added to a cold water/ sat. sodium bicarbonate mixture (2:1, 20 ml). The solvents were filtered and the residue was taken in DCM. The organic layer was dried with Na2SO4, filtered and the filtrate was evaporated to dryness to give the product as a beige solid. Used as such.

According to the analysis of related databases, 13627-49-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; OSLO UNIVERSITY HOSPITAL HF; FORSCHUNGSVERBUND BERLIN E.V.; UNIVERSITY OF OULU; KRAUSS, Stefan; NAZARE, Marc; ANUMALA, Upendra Rao; LEHTIO, Lari; WAALER, Jo; HOLSWORTH, Dan; WEGERT, Anita; LEENDERS, Ruben Gerardus George; (99 pag.)WO2018/118868; (2018); A1;,
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