Category: 10244-24-3

Synthetic Route of 10244-24-3 ,Some common heterocyclic compound, 10244-24-3, molecular formula is C12H17ClN4O2, 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.

4,4 ‘ – (6-chloro-pyrimidine -2,4-diyl) two morpholine (210 mg, 0 . 74mmol), 3 – (2-amino-5-bromo-(trifluoromethyl) pyridin-3-yl) acrylic acid methyl ester (480 mg, 1 . 47mmol),were taken and then palladium acetate (34 mg, 0 . 15mmol), n-butyl, di (1-adamantyl) diphenylphosphinobiphenyl (80 mg, 0 . 22mmol), pinacone esterjoint boric acid (470 mg, 1 . 9mmol) and cesium carbonate (842 mg, 2 . 6mmol) were added to the toluene (10 ml) and methanol (10 ml) under the protection of nitrogen and the temperature was raised to 75 C reaction for 16 hours. adding water (50 ml), dichloromethane (100 ml) extraction, the organic phase with saturated salt water (60 ml) washing, drying by anhydrous sodium sulfate, concentrated, crude product by silica gel column chromatography (dichloromethane: methanol =20:1) purified title compound (320 mg, yield 87.6%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,10244-24-3, its application will become more common.

Reference:
Patent; Shandong Xuan Bamboo Pharmaceutical Technology Co., Ltd.; Wu, Yong qian; (49 pag.)CN105461714; (2016); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 10244-24-3, 4,4′-(6-Chloropyrimidine-2,4-diyl)dimorpholine, 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, SDS of cas: 10244-24-3, blongs to pyrimidines compound. SDS of cas: 10244-24-3

A solution of 40 g of 2,4-[bis-morpholino]-6-chloropyrimidine and 34 g of piperazine in 60 g of pyridine is heated at 100 for 24 h. The mixture is partitioned between methylene chloride and aqueous potassium carbonate. The organic phase is filtered through sodium sulfate and concentrated. The residue is chromatographed (methylene chloride to 4% methanol/1% ammonium hydroxide/methylene chloride) to give the title compound, NMR (CDCl3) 2.90, 3.50, 3.75, 3.80 and 5.10 delta.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,10244-24-3, 4,4′-(6-Chloropyrimidine-2,4-diyl)dimorpholine, and friends who are interested can also refer to it.

Reference:
Patent; Upjohn Company; US5099019; (1992); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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 10244-24-3, name is 4,4′-(6-Chloropyrimidine-2,4-diyl)dimorpholine. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of 4,4′-(6-Chloropyrimidine-2,4-diyl)dimorpholine

The 4,4 ‘ – (6-chloro-pyrimidine -2,4-diyl) two morpholine (301 mg, 1 . 06mmol), 7-bromo-8 – (trifluoromethyl) – 3,4-dihydro -2H-pyrido [3,2-b] [1,4] oxazine (200 mg, 0 . 71mmol),were taken and then duplex pinacone borate (350 mg, 1 . 38mmol), cesium fluoride (500 mg, 3 . 3mmol), palladium acetate (20 mg, 0 . 09mmol) and butyl b (1-adamantyl) diphenylphosphinobiphenyl (64 mg, 0 . 18mmol), were sequentially added to the toluene and methanol (4 ml, 1:1) in the mixed solvent, and added to the above mentioned solution, under nitrogen protection,at 70 C oil bath for 1 hour. After the reaction, concentrating, separating TLC (petroleum ether: ethyl acetate = 1:2), to obtain the title compound (45 mg, yield 14%).

With the rapid development of chemical substances, we look forward to future research findings about 10244-24-3.

Reference:
Patent; Shandong Xuan Bamboo Pharmaceutical Technology Co., Ltd.; Wu, Yong qian; (49 pag.)CN105461714; (2016); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 10244-24-3, 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. 10244-24-3, name is 4,4′-(6-Chloropyrimidine-2,4-diyl)dimorpholine, molecular formula is C12H17ClN4O2, 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.

General procedure: 2,4,6-trichlorotriazine (1.84 g, 0.01 mol)Soluble in anhydrous acetone (10 mL), ice-salt bath cooled to -10 C,Morpholine (1.74 mL, 0.02 mol)And triethylamine (2.02 g, 0.02 mol)Of the mixed liquid droplets added to the reaction system, 0 C reaction 3h, room temperature reaction 3h.The mixture was poured into crushed ice, filtered, washed with water and dried to give 2.70 g of a white solid, 94.4% yield

According to the analysis of related databases, 10244-24-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Xi’an Jiaotong University; YU, YAN; WANG, XIAO MENG; ZHANG, SAN QI; HU, SEN KE; LU, SHE MIN; MEI, QI BING; (10 pag.)CN104151256; (2016); B;,
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. 10244-24-3, name is 4,4′-(6-Chloropyrimidine-2,4-diyl)dimorpholine, the common compound, a new synthetic route is introduced below. Quality Control of 4,4′-(6-Chloropyrimidine-2,4-diyl)dimorpholine

The 4,4 ‘ – (6-chloro-pyrimidine -2,4-diyl) two morpholine (5.0g, 17 . 6mmol), pinacone esterjoint boric acid (5.8g, 22 . 8mmol) and potassium acetate (2.59g, 26 . 4mmol) into acetonitrile (100 ml) in, under the protection of nitrogen by adding three ring hexyl phosphine (395 mg, 1 . 4mmol) and three (dibenzalacetone) palladium II (645 mg, 0 . 7mmol), the temperature is increased to 84 C reaction 3 hours, to take advantage of heat filtering, the filtrate after turns on lathe does adding toluene (30 ml) and petroleum ether (100 ml), stirring, precipitate, filtered, the filter cake is washed with petroleum ether washing, to obtain the title compound (3.8g, yield 57.4%).

The synthetic route of 10244-24-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shandong Xuanzhu Oharma Co., Ltd.; Wu, Yongjian; (47 pag.)CN105541792; (2016); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 10244-24-3, Adding some certain compound to certain chemical reactions, such as: 10244-24-3, name is 4,4′-(6-Chloropyrimidine-2,4-diyl)dimorpholine,molecular formula is C12H17ClN4O2, 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 10244-24-3.

A solution of 40 g of 2,4-[bis-morpholino]-6-chloropyrimidine and 34 g of piperazine in 60 g of pyridine is heated at 100 for 24 h. The mixture is partitioned between methylene chloride and aqueous potassium carbonate. The organic phase is filtered through sodium sulfate and concentrated. The residue is chromatographed (methylene chloride to 4% methanol/1% ammonium hydroxide/methylene chloride) to give the title compound, NMR (CDCl3) 2.90, 3.50, 3.75, 3.80 and 5.10 delta.

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. 10244-24-3, 4,4′-(6-Chloropyrimidine-2,4-diyl)dimorpholine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Upjohn; US5120843; (1992); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 10244-24-3, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 10244-24-3 as follows.

Example 8: Preparation of Trianion of 5-bromo-4-(trifluoromethyl)pyridin-2-amine using 3.5 Equivalents of Isopropylmagnesium chloride, lithium chloride complexA reactor was charged with 5-bromo-4-(trifluoromethyl)pyridin-2-amine (1.000 g, 4.149 mmol) and tetrahydrofuran (7.72 ml). The mixture was sitrred for 10 minutes. The mixture was cooled to 0 C within 30 minutes. lsopropylmagnesiumcloride lithium chloride 1 .3M in THF (6.383 ml,8.298 mmol) was continuously added within a time period of 1.5 hours at 0 C. An additional1.5 equivalents of isopropylmagnesiumcloride lithium chloride 1 .3M in THF (4.788 ml, 6.224 mmol) was continuously added within a time period of 1 .5 hours at 0 C. An additional 0.5 equivalents of isopropylmagnesiumcloride lithium chloride 1 .3M in THF (1 .596 ml, 2.075 mmol) was continuously added within a time period of 1 hour at 0 C. The product was the trianion of 5-bromo-4-(trifluoromethyl)pyridin-2-amine, as determined by HPLC and LCMS.Example 9: Preparation of 5-(2,6-Di-4-morpholinyl-4-pyrimidin-4-yl)-4- (trifluoromethyl)pyridin-2-amine (Compound A)The compound 4,4?-(6-chloropyrimidine-2,4-diyl)dimorpholine (0.40g, 1.405 mmol), 1,1?- Bis(diphenylphosphino)ferrocene (0.040g, 0.070 mmol) and Palladium acetate (0.016g, 0.070 mmol) and 2 mL of tetrahydrofuran were placed in an inertized reactor. The reactor is evacuated to 100 mbar and flushed with nitrogen two times. lsopropylmagnesiumcloride lithium chloride 1 .3M in THF (1.405 mmol) was added at 30 C followed by an equivalent amount of the trianion of 5-bromo-4-(trifluoromethyl)pyridin-2-amine (1.405 mmol). The suspension was stirred for 0.5 hours. The product was 5-(2,6-Di-4-morpholinyl-4-pyrimidin-4-yl)-4- (trifluoromethyl)pyridin-2-amine, as determined by HPLC and LCMS.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,10244-24-3, its application will become more common.

Reference:
Patent; NOVARTIS AG; FLUBACHER, Dietmar; BIERI, Nicole; ACEMOGLU, Murat; MICHEL, Pascal; MOSE, Rasmus; STETTLER, Hans; TESTA, Maria Caterina; BROZIO, Joerg; SCHAEFER, Frank; WO2014/64058; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 10244-24-3, 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.10244-24-3, name is 4,4′-(6-Chloropyrimidine-2,4-diyl)dimorpholine, molecular formula is C12H17ClN4O2, molecular weight is 284.74, as common compound, the synthetic route is as follows.

Step 1. To a solution of 4,4′-(6-chloropyrimidine-2,4-diyl)dimorpholine (1.0 equiv.) and Intermediate A (1.1 equiv.) in DME and 2M sodium carbonate (3:1, 0.2 M) was added PdCl2(dppf)-DCM adduct (0.500 equiv.) in a microwave vial equipped with a stir bar. The reaction was heated to 120 C. for 20 min in the microwave. The organic phase was dried with sodium sulfate, filtered and concentrated. The crude material was purified via preparative reverse phase HPLC. Upon lyophilization of the pure fractions, N-(3-(2,6-dimorpholinopyrimidin-4-yl)-4-methylphenyl)-3-(trifluoromethyl)benzamide was isolated as the TFA salt in 37% yield. LCMS (m/z) (M+H)=528.3, Rt=0.80 min, 1H NMR (400 MHz, ) delta ppm 2.21-2.35 (m, 3H) 3.68 (br. s., 8H) 3.71 (d, J=4.30 Hz, 8H) 6.50 (br. s., 1H) 7.34 (d, J=8.22 Hz, 1H) 7.70-7.89 (m, 3H) 7.97 (d, J=7.83 Hz, 1H) 8.26 (d, J=7.83 Hz, 1H) 8.29 (s, 1H) 10.59 (br. s., 1H).

The chemical industry reduces the impact on the environment during synthesis 10244-24-3, I believe this compound will play a more active role in future production and life.

Reference:
Patent; NOVARTIS AG; Barsanti, Paul A.; Burger, Matthew; Lou, Yan; Nishiguchi, Gisele; Polyakov, Valery; Ramurthy, Savithri; Rico, Alice; Setti, Lina; Smith, Aaron; Taft, Benjamin; Tanner, Huw; DiPesa, Alan; Yusuff, Naeem; US2014/275003; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 10244-24-3, 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. 10244-24-3, name is 4,4′-(6-Chloropyrimidine-2,4-diyl)dimorpholine. A new synthetic method of this compound is introduced below.

A reactor was charged with N-(5-bromo-4-(trifl uoromethyl)pyrid in-2-yl )acetamide (1 .405 m mol)and tetrahydrofuran (2 mL). The mixture was sitrred for 10 minutes. The mixture was cooled to0 C within 30 minutes. lsopropylmagnesiumcloride lithium chloride 1 .3M in THF (ml, 1.405mmol) was continuously added within a time period of 1 hour at 0 C. An additional 1.5 equivalents of isopropylmagnesiumcloride lithium chloride 1 .3M in THF (4.788 ml, 2.107 mmol) was continuously added within a time period of 1 .5 hours at 0 C. The product was the dianion of N-(5-bromo-4-(trifluoromethyl)pyridin-2-yl)acetamide, as determined by HPLC and LCMS.The compound 4,4?-(6-chloropyrimidine-2,4-diyl)dimorpholine (0.40g, 1.405 mmol), 1,1?- Bis(diphenylphosphino)ferrocene (0.040g, 0.070 mmol) and Palladium acetate (0.016g, 0.070 mmol) and 2 mL of tetrahydrofuran were placed in an inertized reactor. The reactor is evacuated to 100 mbar and flushed with nitrogen two times. lsopropylmagnesiumcloride lithium chloride 1 .3M in THF (1.405 mmol) was added at 30 C followed by an equivalent amount of the dianion of N-(5-bromo-4-(trifluoromethyl)pyridin-2-yl)acetamide (1.405 mmol) and 1- iodoadamantane (0.41 3g, 1 .405 mmol). The suspension was stirred for 0.5 hours. The product was N-(5-(2,6-dimorpholinopyrimidin-4-yl)-4-(trifluoromethyl)pyridin-2-yl)acetamide as determined by HPLC and LCMS.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,10244-24-3, 4,4′-(6-Chloropyrimidine-2,4-diyl)dimorpholine, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; FLUBACHER, Dietmar; BIERI, Nicole; ACEMOGLU, Murat; MICHEL, Pascal; MOSE, Rasmus; STETTLER, Hans; TESTA, Maria Caterina; BROZIO, Joerg; SCHAEFER, Frank; WO2014/64058; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 10244-24-3 , The common heterocyclic compound, 10244-24-3, name is 4,4′-(6-Chloropyrimidine-2,4-diyl)dimorpholine, molecular formula is C12H17ClN4O2, 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.

Example 4 Preparation of Buparlisib (0036) Added compound 6 (14.4 g, 0.06 mol), bis(pinacolato)diboron (compound 5) (18.2 g, 0.072 mol), DMSO (200 mL), KOAc (17.64 g, 0.18 mol) and PdCl2(PPh3)2 (4.2 g, 0.006 mol) into a second reactor, then heated the resulting mixture to 5 C. and kept the reaction for 7 hours, and then added compound 4 (17 g, 0.06 mol) into the second reactor, kept the reaction for 16 hours. Put the reaction solution into water after the reaction was finished, and large amount of solid were separated. The resulting mixture was filtered, stirred with methanol/acetone (V:V=1:1) and crystallized for 3 hours. The filter cake was dried in vacuo at 60 C. for 8 hours to obtain the buparlisib product (compound 1) as a white solid (23.15 g, yield 94%), HPLC purity: 99.2%. Mass Spectrum: M+H- 411.

The synthetic route of 10244-24-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; XU, YONG; (6 pag.)US2016/264546; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia