Day: November 5, 2020

720-01-4, 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. 720-01-4, name is Ethyl 4-chloro-2-trifluoromethylpyrimidine-5-carboxylate, molecular formula is C8H6ClF3N2O2, 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 ethyl-4-chloro-2-(trifluoromethyl)pyrimidin-5-carboxylate (24) (510 mg, 2.0 mmol) in DCM (10 ml_) at 0C was added diisobutylaluminum hydride (1 M solution in toluene) (6.0 ml_, 6.0 mmol). The mixture was slowly allowed to warm to room temperature and was stirred overnight. The reaction mixture was quenched with sat. aq. Rochelle’s salt and stirred for 30 min before concentrating down the solution. The product was then extracted into EtOAc (3 x 30 ml_) and the combined organic layers were washed with brine (50 ml_), dried (MgS04) and solvent evaporated to leave a clear oil. The crude was purified by column chromatography (S1O2, 10 g, gradient elution 10% EtOAc in petrol to 50% EtOAc in petrol). The desired fractions were concentrated under reduced pressure to afford the title compound as a yellow oil (96 mg, 23%); 1H NMR (500 MHz, Chloroform- d) d 9.01 (s, 1 H), 4.92 (s, 2H); LCMS (4 minute method) product at Rt = 0.44 min and ES+ m/z the desired mass ion was not observed.

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. 720-01-4, Ethyl 4-chloro-2-trifluoromethylpyrimidine-5-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE UNIVERSITY OF SUSSEX; CARDIFF UNIVERSITY; UNIVERSITY COLLEGE CARDIFF CONSULTANTS LIMITED; WARD, Simon; BESWICK, Paul; PENNICOTT, Lewis; REUILLON, Tristan; CHUCKOWREE, Irina; VILLALONGA-BARBER, Carolina; PORTER, Roderick, Alan; (120 pag.)WO2019/166822; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

65-71-4, 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 65-71-4, name is 5-Methylpyrimidine-2,4(1H,3H)-dione. This compound has unique chemical properties. The synthetic route is as follows.

Was added to the reactor5-methylthymidine20-2 (0.530 g, 4.2 mmol),Compound 21-1 (0.328 g, 1.4 mmol) and40 ml of anhydrous acetonitrile, argon was added dropwise to the solution at room temperatureBis (trimethylsilyl) acetamide(2.2 mL, 8.7 mmol),After stirring for 3 hours, the temperature was lowered to -30 C,To the system was added trimethylsilyl trifluoromethanesulfonate (1 mL, 5.6 mmol)Stir at room temperature, TLC followed the reaction.The reaction product was added with dichloromethane,The organic layers were washed with saturated sodium bicarbonate solution, water and saturated brine, respectively,Dried, concentrated, column chromatography (MeOH: CHCl3 = 3: 100)And purified to give the title product 21-2 (yield 70%).

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 65-71-4, 5-Methylpyrimidine-2,4(1H,3H)-dione.

Reference:
Patent; Soochow University (Suzhou); Zou Jianping; Zhang Peizhi; Li Jianan; (13 pag.)CN106496130; (2017); A;,
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. 1193-24-4, name is 4,6-Dihydroxypyrimidine. This compound has unique chemical properties. The synthetic route is as follows. 1193-24-4

Example 15A 5-(4-Methoxyphenyl)furo[2,3-d]pyrimidin-4(3H)-one Analogously to a literature procedure [D. Dauzonne, Tetrahedron, 1992, 3069-3080], a suspension of 10.1 g (47.4 mmol) of 1-[(Z)-2-chloro-2-nitrovinyl]-4-methoxybenzene and 5.8 g (52.2 mmol) of 4,6-dihydroxypyrimidine in 200 ml of ethanol is stirred at 85 C. for ten minutes. 15.6 ml (15.9 g, 104.3 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene are then added slowly. The mixture is stirred at this temperature for 15 h and then concentrated under reduced pressure. The residue is taken up in dichloromethane and chromatographed on silica gel (mobile phase: dichloromethane/methanol 95:5). The solid obtained is triturated with acetonitrile and filtered. This gives 2.3 g (20% of theory) of the target product. LC-MS (method 3): Rt=1.57 min.; m/z=290 (M+H)+ 1H-NMR (400 MHz, CDCl3): delta=12.66 (s, NH), 8.15 (s, 1H), 8.14 (s, 1H), 7.92 (d, 2H), 6.98 (d, 2H), 3.79 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1193-24-4, 4,6-Dihydroxypyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; US2011/166163; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
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. 32779-36-5, name is 5-Bromo-2-chloropyrimidine. A new synthetic method of this compound is introduced below., 32779-36-5

To a solution of 5-bromo-2-chloropyrimidine (4 g, 20.68 mmol) in acetonitrile (40 mL) was added 2-methoxyethanamine (5.5 mL, 63 mmol) and potassium carbonate (14 g, 100 mmol) . The mixture was heated at 100 and stirred for 6 h. The reaction mixture was concentrated to remove solvent. The residue was diluted with water (30 mL) . The resulting mixture was extracted with DCM (50 mL ¡Á 3) . The combined organic layers were dried over anhydrous Na2SO4and concentrated in vacuo. The residue was purified by silica gel column chromatography eluted with PE/EtOAc (v/v) 9/1 to give a colorless oily product (4.43 g, 92.3) .[1798]MS (ESI, pos. ion) m/z: 233.2 [M+1]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,32779-36-5, 5-Bromo-2-chloropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; LIU, Bing; ZHANG, Yingjun; CHENG, Changchung; HUANG, Jiuzhong; BAI, Shun; REN, Xingye; LI, Zhi; ZHOU, Youbai; (368 pag.)WO2016/615; (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. 591-55-9, name is 5-Aminopyrimidine. This compound has unique chemical properties. The synthetic route is as follows. 591-55-9

Example 52: (R)-3-(l-Phenyl-cycloheptanecarbonyIoxy)-l-(pyrimidin-5- ylcarbamoylmethyl)-l-azonia-bicyclo[2.2.2]octane chloridea) 2-ChloiO-/V-pyrimidin-5-yl-acetamide 5-Aminopyrimidine (450 mg) was suspended in DCE (2 mL) and acetonitrile (2 mL) : microwave vial. Chloroacetyl chloride (0.377 mL) was added with stirring. The vial sealed and the reaction mixture was heated in the microwave at 800C for 5 minutes. T solid was filtered off, washed with acetonitrile (2 x 5 mL), DCE (2 x 5 mL) and penta x 30 mL) and then partioned between saturated sodium bicabonate and DCE (50 mL/* mL ) ensuring the aqueous layer was still basic. The organic layer was separated and t aqueous layer was extracted with DCE (2 x 75 mL). The combined organic layer was over magnesium sulfate and evaporated to give the sub-titled compound (200 mg) as i yellow solid.1H NMR (400 MHz, DMSO-D6): delta 10.71 (s, IH), 9.00 (s, 2H), 8.93 (s, IH), 4.35 (s, _

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, 591-55-9, 5-Aminopyrimidine.

Reference:
Patent; ASTRAZENECA AB; ARGENTA DISCOVERY LIMITED; WO2009/138707; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

137234-74-3, Adding a certain compound to certain chemical reactions, such as: 137234-74-3, 4-Chloro-6-ethyl-5-fluoropyrimidine, 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, 137234-74-3, blongs to pyrimidines compound.

To the stirred solution of 4-chloro-6-ethyl-5-fluoro pyrimidine 1 (10 gm, 62.50 mmol) in CCl4 (150 mL) was added N-bromosuccinimide (12.7 gm, 71.35 mmol) and AIBnu (511 mg, 3.12 mmol). The reaction mixture was refluxed for 4 hrs at 75 C. The progress of the reaction was monitored by TLC. The reaction mixture then diluted with DCM (500 mL) and washed successively with water, sodium meta bisulphite (100 mL) solution, water and brine solution. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain the bromide 2 as yellowish oily syrup (14 gm, 58.58 mmol, 94%). 1H NMR (CDCl3, 500 MHz): 2.10 (d, 3 H), 5.40 (q, 1 H), 8.80 (s, 1 H). Mass: 241(M++2)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,137234-74-3, its application will become more common.

Reference:
Patent; VIAMET PHARMACEUTICALS, INC.; WO2008/64311; (2008); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

A common compound: 1004-38-2, name is 2,4,6-Triaminopyrimidine,molecular formula is C4H7N5, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below., 1004-38-2

EXAMPLE 1 2,4-Diaminopyrido[2,3-d]pyrimidine-6-carboxaldehyde (III) Phosphorus oxychloride (27.5 ml, 46.0 g, 300 mmol) was added over 15 minutes with stirring to N,N-dimethylformamide (11.0 g, 150 mmol), which was cooled with an ice bath. After stirring at room temperature for 1 hour, the reaction mixture was treated with bromoacetic acid (13.9 g, 100 mmol). The resulting solution, protected by a calcium chloride tube was heated at 92 C. for 10 hours and evaporated to dryness in vacuo. The colored oil (~30 g) was dissolved in water (1000 ml), and the solution was neutralized with 50% sodium hydroxide to pH 7. After addition of 2,4,6-triaminopyrimidine (5.00 g, 40.0 mmol), the solution was refluxed for 3 hours and filtered hot through a fluted filter. The filtrate was cooled and the solid that precipitated was collected by filtration and dried in vacuo over P2 O5: yield, 2.53 g (33%). Mass spectrum, m/e 189 (M+). HPLC [ 0.1 M NH4 OAc (pH 3.6) –CH3 OH (9:1)] indicated that this product was 86% pure. A sample (200 mg) was dissolved in 0.1 N HCl (15 ml) and diluted with acetone (225 ml) to precipitate impure III: yield, 91 mg. The filtrate was evaporated to dryness under reduced pressure and the residue was dried in vacuo over P2 O5 to give compound III:

With the rapid development of chemical substances, we look forward to future research findings about 1004-38-2.

Reference:
Patent; Southern Research Institute; US4431805; (1984); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

A common compound: 1722-12-9, name is 2-Chloropyrimidine,molecular formula is C4H3ClN2, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below., 1722-12-9

General procedure: The Buchwald-Hartwig amination reaction under microwave irradiation was conducted in a CEM Discover apparatus. A 10-mL Teflon vessel was charged with 1.0 mmol of hetero-aryl halide, 3.0 mmol of amine, 2.0 of mmol base, 0.05 mmol of Pd(OAc)2 , 0.10 mmol of LHX, and 2.0 mL of solvent. The mixture was irradiated at 150 W at 100 C for the specified time and then allowed to cool. The reaction mixture was extracted 3 times with diethyl ether, and the combined organic extracts were washed with water, dried (MgSO4) , and evaporated to dryness. Purification of the residue by flash chromatography on silica gel afforded the pure products.

With the rapid development of chemical substances, we look forward to future research findings about 1722-12-9.

Reference:
Article; Yang, Liangru; Bian, Huanyu; Mai, Wenpeng; Mao, Pu; Xiao, Yongmei; Wei, Dong; Qu, Lingbo; Turkish Journal of Chemistry; vol. 39; 1; (2015); p. 121 – 129;,
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. 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, the common compound, a new synthetic route is introduced below. 130049-82-0

Example 4; Preparation of Crude Paliperidone Using N,N-Dimethyl Amino Pyridine (DMAP)A 100 ml Flask equipped with a mechanical stirrer, reflux condenser was charged with CMHTP (7.15 gm), FBIP.HCl (5 gm), diisopropyl ethyl amine (6.5 gm), 4-N,N-dimethyl amino pyridine (0.125 gm) and methanol (50 ml) and stirred at room temperature. The reaction mixture was then refluxed at 60-70 C. for 8 to 10 hr. After completion of the reaction the reaction mixture was cooled to 0 C. and the product obtained was filtered and suck dried. The wet product was dried under vacuum at 50-55 C.Crude Paliperidone: 99.7%N-Oxide Impurity: 0.06%Carboxylate impurity: Not detected

Statistics shows that 130049-82-0 is playing an increasingly important role. we look forward to future research findings about 3-(2-Chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidine-4-one.

Reference:
Patent; ORCHID CHEMICALS & PHARMACEUTICALS LTD.; US2012/165527; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

171887-03-9 , The common heterocyclic compound, 171887-03-9, name is N-(2-Amino-4,6-dichloropyrimidine-5-yl)formamide, molecular formula is C5H4Cl2N4O, 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.

5.7 mmol) and DIPEA (2.6 mL; 15.2 mmol) were added to a solutionof 3-amino-1-trityloxymethylphospholane 1-oxide 15 (1.5 g;3.8 mmol) in n-butanol (50 mL). The reaction mixture was stirredfor 40 h at 130 C and evaporated. 3-(2-Amino-6-chloropurine-9-yl)-1-trityloxymethylphospholane 1-oxide 23 was purified bychromatography on silica gel (first isocraticwash with 50% acetone/toluene, second elution with gradient of 0e10% ethanol in chloroform).ESI-MS calcd for C29H28ClN5O2P (M H) 544.2, 546.2 found544.1, 546.1.

According to the analysis of related databases, 171887-03-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Pav, Ond?ej; Bud??insky, Milo?; Rosenberg, Ivan; Tetrahedron; vol. 73; 34; (2017); p. 5220 – 5228;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia