Month: March 2021

Related Products of 1780-36-5, 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. 1780-36-5, name is 2,4,6-Trichloro-5-methylpyrimidine. A new synthetic method of this compound is introduced below.

(c) Production of 4-amino-2,6-dichloro-5-methylpyrimidine 39.5 g (0.2 mol) of 5-methyl-2,4,6-trichloropyrimidine are dissolved in 250 ml of dimethoxyethane, and ammonia gas is then introduced at room temperature until the solution is saturated. A white suspension is formed, which is stirred for 12 hours at room temperature; it is subsequently concentrated in a rotary evaporator, and 200 ml of water are added to the residue. The formed suspension is filtered and the precipitate is dried. The mother liquor is concentrated to half the volume, filtered, and the precipitate is dried. There are thus obtained 26.4 g of crude product, which is recrystallized from acetonitrile/water (5:1); m.p. 193-194 C. (yield=75% of theory). Analysis: calculated: C 33.74%, H 2.83%, N 23.61%, Cl 39.83%, found: C 33.80%, H 2.87%, N 23.44%, Cl 39.51%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1780-36-5, 2,4,6-Trichloro-5-methylpyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Ciba-Geigy Corporation; US4741760; (1988); A;,
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.4316-93-2, name is 4,6-Dichloro-5-nitropyrimidine, molecular formula is C4HCl2N3O2, molecular weight is 193.9756, as common compound, the synthetic route is as follows.Product Details of 4316-93-2

General procedure: To a stirred solution of 4,6-dichloro-5-nitropyrimidine (1.5mmol), amine (0.5mmol), Pd2(dba)3 (0.01mmol), R-BINAP (0.03mmol) and potassium carbonate (0.7mmol) in toluene (5mL) at room temperature and the mixture was under an argon atmosphere for 3.5h. The resulting reaction mixture was filtered and evaporated. The residue was purified by column chromatography on silica gel.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,4316-93-2, 4,6-Dichloro-5-nitropyrimidine, and friends who are interested can also refer to it.

Reference:
Article; Liu, Meng-Meng; Mei, Qiong; Zhang, Yi-Xiao; Bai, Peng; Guo, Xiang-Hai; Chinese Chemical Letters; vol. 28; 3; (2017); p. 583 – 587;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 4316-93-2 ,Some common heterocyclic compound, 4316-93-2, molecular formula is C4HCl2N3O2, 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 solution of 2′,3′-O-Isopropylidene-beta-D-ribofuranosylamine p-toluenesulfonate salt (2.65 g, 7.34 mmol) in 30 mL of N,N-dimethylformamide at room temperature was treated first with triethylamine (2.3 mL, 16.7 mmol) followed by the slow addition of 4,6-dichloro-5-nitropyrimidine (1.30 g, 6.68 mmol). After stirring for 3 h, the yellow solution was diluted with ethyl acetate (50 mL) and washed with water (50 mL). The aqueous phase was further extracted with 2*20 mL of ethyl acetate and the combined organic extracts were washed with 2*50 mL of brine, dried over MgSO4, filtered and concentrated in vacuo. The resulting crude product was purified by silica gel chromatography (3:1 hexane/ethyl acetate) to afford 6-chloro-5-nitro-4-(2,3-O-isopropylidene-beta-D-ribofuranosylamino)pyrimidine (1.37 g, 59%) as a white powder (m.p. 117-119 C.). TLC Rf 0.3 (3:1 hexane/ethyl acetate). 1H NMR (CDCl3, 300 MHz): delta 8.71 (1H, d, J=8.7 Hz), 8.43 (1H, s), 6.35 (1H, d, J=8.7 Hz), 4.93 (1H, J=6.0 Hz), 4.69 (1H, d, J=6.0 Hz), 4.44 (1H, s), 3.88 (2H, dd, J=3.6 Hz, 1.8 Hz), 2.81 (1H, dd, J=2.4 Hz, 2.1 Hz), 1.57 (3H, s), 1.36 (3H, s). MS (ES+): 347.

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. 4316-93-2, 4,6-Dichloro-5-nitropyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Wilde, Richard G.; Almstead, Neil G.; Welch, Ellen M.; Beckmann, Holger; US2006/166926; (2006); 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. 5305-40-8, name is 4,6-Dichloropyrimidine-5-carbaldehyde. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 5305-40-8

The compound 4,6-dichloropyrimidine-5-carbaldehyde (5 g, 28.25 mmol) was suspended in dry MeOH (100 mL)After K2CO3 (7.8 g, 56.5 mmol) was added thereto, the reaction mixture was stirred at 90 C for 1 hour and then concentrated under reduced pressure to giveThe residue was dissolved in a mixed solvent of water (100 mL) and DCM (100 mL), separated on a liquid phase, the aqueous phase was extracted with DCM (50 mL ¡Á 3)The combined organic phases were concentrated under reduced pressure, the residue was diluted in DCM / PE (1 mL / 20 mL) and the resulting mixture stirred at room temperatureThe mixture was stirred for 3 hours and then filtered off with suction to give a yellow solid which was purified by silica gel column chromatography (PE / EtOAc (v / v) = 5/1)Purification gave the title compound as a white solid (2.2 g, 46.3%).

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, 5305-40-8, 4,6-Dichloropyrimidine-5-carbaldehyde.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jiatuo Sciences Corporation; Xi Ning; Wang Liang; Wu Zuping; Feng Xuejin; Wu Yanjun; (154 pag.)CN104513235; (2017); B;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 50593-91-4, 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. 50593-91-4, name is Methyl 5-bromo-2-(methylthio)pyrimidine-4-carboxylate. A new synthetic method of this compound is introduced below.

Preparation 31 : (¡ê)-methyl 5-(2-ethoxyvinyl)-2-(methylthio)pyrimidine-4-carboxylate A solution of (¡ê)-2-(2-ethoxyvinyl)-4,4,5,5-tetramethyl-1 ,3,2-dioxaborolane (Preparation 29, 4.34 g, 21 .91 mmol), methyl 5-bromo-2-(methylthio)pyrimidine-4-carboxylate (Preparation 30, 3.81 g, 14.48 mmol) and Pd(dppf)CI2 DCM (505 mg, 0.618 mmol) was dissolved in THF (45 mL) and 2M sodium carbonate in water (15 mL) and heated to 65 C for 18 hours. The mixture was diluted with EtOAc and quenched with brine. The aqueous layer was extracted with EtOAc three times. The combined organic layers were washed with water and brine, dried and concentrated. The residue was purified by silica gel column chromatography eluting with 0 to 10% EtOAc in cyclohexane to give the title compound (2.30 g, 63%). 1 H NMR (500 MHz, CDCI3) : delta 8.67 (s, 1 H), 6.96 (d, J = 13.1 Hz, 1 H), 6.26 (d, J = 13.1 Hz, 1 H), 4.13 – 3.81 (m, 5H), 2.60 (s, 3H), 1 .37 (t, J = 7.0 Hz, 3H). LCMS (ESI) Rt = 2.49 minutes MS m/z 255 [M+H]+

At the same time, in my other blogs, there are other synthetic methods of this type of compound,50593-91-4, Methyl 5-bromo-2-(methylthio)pyrimidine-4-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; HOELDER, Swen; BLAGG, Julian; SOLANKI, Savade; WOODWARD, Hannah; NAUD, Sebastian; BAVETSIAS, Vassilios; SHELDRAKE, Peter; INNOCENTI, Paolo; CHEUNG, Jack; ATRASH, Butrus; WO2014/37750; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 13223-25-1 ,Some common heterocyclic compound, 13223-25-1, molecular formula is C6H7ClN2O2, 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 suspended tetramethyl-ammonium nitrate (11.2 g, 39.5 mmol) in methylene chloride (100 mL) was added triflic anhydride (5.4 g, 39.5 mmol), and stirred at room temperature for 2 hour. After the resultant was cooled to -78 C., a solution of 2-chloro-4,6-dimethoxypyrimidine (5.0 g, 36.0 mmol) in methylene chloride (50 mL) was added at -78 C., and continued to stirred at room temperature for 24 hours. The reaction was diluted with brine, extracted with ethyl acetate, washed with brine, dried over Na2SO4, concentrated to yield 2-chloro-4,6-dimethoxy-5-nitro-pyrimidine (25) (6.0 g, 76%). 1HNMR (DMSO-d6)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,13223-25-1, its application will become more common.

Reference:
Patent; DECODE GENETICS EHF; US2009/130076; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 183438-24-6, 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. 183438-24-6, name is 5-Bromo-2-iodopyrimidine, molecular formula is C4H2BrIN2, 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.

5-bromo-2-iodopyrimidine (16.7 g, 58.8 mmol) was dissolved in DCM (200 mL) with stirring and cooled to -78 C under N2. 2.5 M n-BuLi in hexane in hexane (23.5 mL) was added dropwise and stirred for 20 minutes at – 78 C. Intermediate 74 (10 g, 58.8 mmol) in DCM (50 mL) was cooled in a dry ice bath and added in one portion. The reaction wasstirred at -78C for 10 minutes. The reaction was quenched by addition of saturated aqueous NH4C1 solution (20 mL) and allowed to warm to r.t, saturated aqueous NH4C1 solution (50 mL) was added and the mixture was extracted with DCM (2 x 100 mL). The combined organic extracts were dried over sodium sulfate and concentrated under vacuum. The crude product was purified by column chromatography using 0 – 30 %EtOAc in heptane to afford the title compound (7.6 g, 35 %) as a yellow solid.OH (500 MHz, CDC13) 8.78 (s, 2H), 5.22 – 5.14 (m, 1H), 3.03 -2.93 (m, 2H), 2.67 – 2.58 (m, 2H), 1.22 (s, 9H).

According to the analysis of related databases, 183438-24-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UCB BIOPHARMA SPRL; SANOFI; DE HARO GARCIA, Teresa; DELIGNY, Michael; HEER, Jag Paul; QUINCEY, Joanna Rachel; XUAN, Mengyang; ZHU, Zhaoning; BROOKINGS, Daniel Christopher; CALMIANO, Mark Daniel; EVRARD, Yves; HUTCHINGS, Martin Clive; JOHNSON, James Andrew; JADOT, Sophie; KEYAERTS, Jean; MAC COSS, Malcolm; SELBY, Matthew Duncan; SHAW, Michael Alan; SWINNEN, Dominique Louis Leon; SCHIO, Laurent; FORICHER, Yann; FILOCHE-ROMME, Bruno; (365 pag.)WO2016/50975; (2016); 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. 14001-67-3, name is 5-Bromo-2-methylthiopyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of 5-Bromo-2-methylthiopyrimidine

A mixture of azetidine (0.03 mL, 0.5 mmol), 5-bromo-2-(methylthio)pyrimidine (100 mg, 0.49 mmol),Xantphos (4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene) (9.9 mg, 0.02 mmol), Pd(OAc)2 (2 mg, 0.01 mmol) and NaOt-Bu (140 mg, 1 .5 mmol) in toluene (1 .7 mL) was heated at 110C. After 3h, the reaction mixture was cooled to room temperature and concentrated under vacuum. Purification (FCC, 5i02, 0-99% EtOAc in hexanes) afforded the title compound (39 mg,44%). MS(ESl): mass calcd. forC8H11N3S, 181.1; m/zfound, 182.1 [M+H]. 1H NMR (400 MHz, DMSO-d5) O 7.96 (s, 2H), 3.87 (t, J = 7.3 Hz, 4H), 2.45 (s, 3H), 2.40 -2.32 (m, 2H).

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, 14001-67-3, 5-Bromo-2-methylthiopyrimidine.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; CHEN, Gang; CHROVIAN, Christa C.; COATE, Heather R.; DVORAK, Curt A.; GELIN, Christine F.; HISCOX, Afton; LETAVIC, Michael A.; RECH, Jason C.; SOYODE-JOHNSON, Akinola; STENNE, Brice; WALL, Jessica L.; ZHANG, Wei; (583 pag.)WO2017/139428; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 22536-61-4, 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 22536-61-4, name is 2-Chloro-5-methylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

(E)-5-Methyl-2-(prop-1-en-1-yl)pyrimidine, Example 11.01 To a 500 mL round bottomed flask was added 2-chloro-5-methylpyrimidine (12 g, 93 mmol), potassium (E)-trifluoro(prop-1-en-1-yl)borate (17.27 g, 117 mmol), and potassium phosphate (59.4 g, 280 mmol). The flask was purged with N2 (5*) and then 1,4-dioxane (200 mL) and water (20 mL) were added. The resulting yellow suspension was bubbled with Ar for 15 min and then 1,1-bis[(di-t-butyl-p-methylaminophenyl]palladium (II) chloride (Amphos, commercially available from Strem, 2.64 g, 3.73 mmol) was added, a reflux condenser was attached, and the reaction was warmed to 90 C. in an oil bath and stirred under N2 for 16.5 h. The reaction was then cooled to RT. The reaction was diluted with water (250 mL), and extracted with EtOAc (2*250 mL). The organic layers were combined, dried (MgSO4), and concentrated. The residue was purified by flash chromatography on silica gel eluting with 0-20% EtOAc/hexanes) to afford (E)-5-methyl-2-(prop-1-en-1-yl)pyrimidine 11.01 (12.96 g, 97 mmol, 100% yield) as a yellow/orange oily solid. 1H NMR (300 MHz, CDCl3) delta=8.49 (s, 2H), 7.01-7.20 (m, 1H), 6.57 (dd, J=15.6, 1.7 Hz, 1H), 2.29 (s, 3H), 1.97 (dd, J=6.8, 1.6 Hz, 3H). LCMS (ESI pos ion) m/z: 135.2 (M+H)+.

According to the analysis of related databases, 22536-61-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AMGEN INC.; CHEN, Xiaoqi; CHEN, Yinhong; CHENG, Alan C.; CONNORS, Richard V.; DEBENEDETTO, Mikkel V.; DRANSFIELD, Paul John; FU, Zice; HARVEY, James S.; HEATH, Julie Anne; HEDLEY, Simon J.; HOUZE, Jonathan; JUDD, Ted C.; KHAKOO, Aarif Yusuf; KOPECKY, David John; LAI, Su-Jen; MA, Zhihua; NISHIMURA, Nobuko; OLSON, Steven H.; PATTAROPONG, Vatee; SWAMINATH, Gayathri; WANG, Xiaodong; YEH, Wen-Chen; (415 pag.)US2017/320860; (2017); 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. 31519-62-7, name is 2-Pyrimidinecarboxylic acid, the common compound, a new synthetic route is introduced below. Computed Properties of C5H4N2O2

Preparation of Intermediate 25 2211 Intermediate 25 2212 [0255] Oxalyl chloride (2.36 mL, 24.2 mmol, 1.5 eq) and a catalytic quantity of DMF were 2213 added to a solution of pyrimidine-2-carboxylic acid (2 g, 16.1 mmol) in dry DCM (30 mL) at 2214 0 C. The resulting mixture was allowed to warm to RT and stir for 3 h. The volatiles were 2215 removed in vacuo and the residue was thoroughly dried to afford pyrimidine-2-carboxylic 2216 acid chloride (2.1 g, 14.8 mmol) as a black solid. The crude material was added portion- wise 2217 to a solution of aminogaunidine sulfate (5.5 g, 22.2 mmol, 1.5 eq) in pyridine (20 mL) at 2218 0 C. The resulting mixture was allowed to warm to RT and stir for 14 h. The mixture was 2219 then neutralized with saturated aqueous NaHCOs, extracted with t-BuOH (5 x 50 mL), dried 2220 over Na2S04, filtered and concentrated in vacuo. The crude material was dissolved in water 2221 (45 mL) and the resulting solution was heated to 100 C for 24 h. The reaction mixture was 2222 then cooled to RT, extracted with t-BuOH (5 x 30 mL), dried over Na2S04, filtered and 2223 concentrated in vacuo to afford Intermediate 25 (650 mg, 25 %) as off-white solid. TLC: 30% 2224 MeOH in CHC13: Rf: 0.20.

The synthetic route of 31519-62-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERSEON, INC.; SHORT, Kevin, Michael; PHAM, Son, Minh; WILLIAMS, David, Charles; KITA, David, Ben; WO2014/145986; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia