Category: pyrimidines

Electric Literature of 55150-17-9 ,Some common heterocyclic compound, 55150-17-9, molecular formula is C6H9N3O, 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.

(2) 2,2,2-Trichloroethyl (4-ethoxyprimidin-5-yl)carbamate; To a solution of 4-ethoxypyrimidine-5-amine (1.00 g, 7.19 mmol) and pyridine (1.74 ml, 21.6 mmol) in tetrahydrofuran (20 ml) was added 2,2,2-trichloroethyl chloroformate (1.49 ml, 10.8 mmol) with ice-cooling, the mixture was stirred for 30 minutes with ice-cooling, the reaction mixture was poured into ice-water and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was recrystallized from a mixed solvent of ethyl acetate and hexane to obtain the desired product (1.73 g, 76.5%) as a solid. 1H-NMR (CDCl3) delta; 1.48 (3H, t, J = 7.2 Hz), 4.55 (2H, q, J = 7.2 Hz), 4.87 (2H, s), 7.15(1H, br s), 8.51 (1H, s), 9.20 (1H, br s).

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. 55150-17-9, 4-Ethoxypyrimidin-5-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP1813606; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 87026-45-7, 4-Chloro-5-methoxy-2-(methylthio)pyrimidine, 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, 87026-45-7, blongs to pyrimidines compound. Safety of 4-Chloro-5-methoxy-2-(methylthio)pyrimidine

4-Chloro-2-methanesulfonyl-5-methoxy-pyrimidine A solution of 3-chloroperoxybenzoic acid (0.4 g, 2.3 mmol) in DCM (2 ml) was added dropwise to a solution of 4-chloro-5-methoxy-2-methylsulfanyl-pyrimidine (0.15 g, 0.78 mmol) in DCM (10 ml) and the mixture was stirred at room temperature for 12 h. Water (10 ml) was added, the aqueous phase was extracted with DCM and concentrated in vacuo. The crude residue was purified by column chromatography with DCM/1% NH3 in MeOH (98:2) as the eluent to give the title compound (0.18 g, 100%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,87026-45-7, its application will become more common.

Reference:
Patent; VIFOR (INTERNATIONAL) AG; US2012/202806; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 60025-06-1, Adding some certain compound to certain chemical reactions, such as: 60025-06-1, name is 1-(4,6-Dichloropyrimidin-5-yl)ethanone,molecular formula is C6H4Cl2N2O, 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 60025-06-1.

Intermediate 21: 4-(4-Chloro-3-methyl-pyrazolo[3,4-d]pyrimidin-1-yl)-piperidine-1-carboxylic acid isopropyl ester; Triethylamine (0.33 mL, 2.4 mmol) was added to a stirred mixture of 4-hydrazino-piperidine-1-carboxylic acid isopropyl ester hydrochloride (Intermediate 10; 188 mg, 0.8 mmol) and 1-(4,6-dichloro-pyrimidin-5-yl)-ethanone (Intermediate 17; 150 mg, 0.8 mmol) in toluene (5 mL) at room temperature under nitrogen and the resulting mixture was heated to reflux for 8 hours. The solvent was removed in vacuo and the crude reaction mixture was purified on a flash silica column (30 mm×4) eluting with 10-33% ethyl acetate/hexanes to give 4-(4-chloro-3-methyl-pyrazolo[3,4-d]pyrimidin-1-yl)-piperidine-1-carboxylic acid isopropyl ester (90 mg, 33%). 1H NMR (300 MHz, DMSO-d6) delta 1.19 (d, 6H, J=6.3 Hz), 1.86-1.99 (m, 4H), 2.63 (s, 3H), 2.94-3.10 (m, 2H), 4.04-4.15 (m, 1H), 4.74-4.82 (m, 1H), 4.91-4.98 (m, 1H), 8.77 (s, 1H).

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. 60025-06-1, 1-(4,6-Dichloropyrimidin-5-yl)ethanone, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Erickson, Shawn David; Gillespie, Paul; Guertin, Kevin Richard; Karnachi, Prabha Saba; Kim, Kyungjin; Ma, Chun; McComas, Warren William; Pietranico-Cole, Sherrie Lynn; Qi, Lida; Tilley, Jefferson Wright; Zhang, Qiang; US2009/286812; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 103365-69-1, 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 103365-69-1, name is (S)-1-Methyl-2,6-dioxohexahydropyrimidine-4-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows.

The taltirelrin was synthesized by using a core-cell (CS) skillsthat can provide amine function in C-terminal and using CS-Rink Amide MBHA. here using a quantitative method it was measured and 0.8 mmol / g loaded resin was used. The synthesis proceeded on 0.1M scale. Synthesis was performed using the fully automated peptidesynthesizer manufactured by SONATA XT a PTI Company. The removal of Fmoc protector of resin. Fmoc protected core-shell (CS) type Rink Amide MBHA Resin(100mmol, 125g, 0.8 mmol / g, beadTechpvt. ltd.) is inserted in a fully automatic peptide synthesizer SONATA XT 3.2L reaction vessel and thendimethylformamide (DMF ) was added and then inserted into the filtered reactorand and was dilated for 30 minutes.after filtration and removal of DMF, then 20% piperidine (in DMF) was put infiltration reactor and then reacted for 10 minutes and filtered, and again 20%piperidine (in DMF) is put and for reacted for 5 minutes and filtered and Fmocremoved rink Amide MBHA resin was prepared. Filtered and the filtrate discarded and the resin remaining inreactor was washed in the following procedure and then filtered: DMF x 2 times(each 5 min), Dichloromethane x 2 times (each 5 min), DMF x 2 times (each 5min) Fmoc-Pro-OH coupling After the Fmoc-Pro-OH 3equivalents was dissolved in DMF, then matching the amino acid equivalent DIC(N, N’-Diisopropylcarbodiimide) and HOBt Cl- (1-Hydroxy-6-Chlorobenzotriazole)is inserted and for about 5 minutes it is activated and inserted in a Fmocprotector removed CS-Rink Amide MBHA resin inserted filteration reactor andthen reacted for 3 hours. After the reaction was completed the reaction solution wasfiltered and the remaining Fmoc-Pro-CS-Rink Amide MBHA resin in the filtrationreactor was washed in the following order: DMF x 2 times (each 5 min),dichloromethane x 2 times ( each 5 min), DMF x 2 times (each 5 min).The reaction termination was confirmed by the color reaction(Kaiser Test). Removal of the Fmoc protector of Fmoc-Pro-CS-Rink Amide Resin In a washed Fmoc-Pro-Rink Amide MBHA resin inserted reactor 20%piperidine (in DMF) is inserted and reacted for 20 minutes and filtered, andagain 20% piperidine (in DMF) is put and for10 minutes It was reacted and then filtered to prepare Fmoc removed H-Pro-CS-Rink Amide MBHA resin. After filtration H-Pro-CS-Rink Amide MBHA resin remaining in thereactor is then washed in following order and then filtered: DMF x 2 times(each 5 min), Dichloromethane x 2 times (each 5 min), DMF x 2 times (each 5min) Fmoc-His (Trt) -OH coupling Fmoc-His (Trt) -OH 3 equivalent after dissolved in DMF, inquantity equivalent of the amino acid DIC and HOBt-Cl is put in and for about 5minutes it is actively refluxed and, then placed in a H-Pro-Rink Amide resininserted filtration reactor and reaction was carried out for 3 hours. After the reaction was completed the reaction solution wasfiltered and the remaining Fmoc-Pro-CS-Rink Amide MBHA resin in the filtrationreactor was washed in the following order: DMF x 2 times (each 5 min),dichloromethane x 2 times ( each 5 min), DMF x 2 times (each 5 min). The reaction termination was confirmed by the color reaction(Kaiser Test). Separation of the peptides from the resin In a Well-dried 1-methyl-4,5-dihydro-orotic acid -His (Trt)-Pro-CS-Rink Amide Resin inserted filtration reactor 10 times volume of resincutting solution (95% TFA, 2.5% TIS,2.5% H2O) is carefully added and reaction was carried out for 3 hours. After completion ethanol10 times the volume of the reaction filtrate is poured and the peptide isextracted. The peptide extracted to remove ethanol is precipitated using acentrifugal separator, and then using two more times ethanol and from the TFAresidue amino acid side chain protectoron removing of residue matter it is dried to yield 36.5g title compound (90%).

According to the analysis of related databases, 103365-69-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; C-TRI Co. Ltd.; Kim, Seok In; Kim, Do Yeong; Im, Chae Yeong; Jeong, Ki Hoon; Kim, Joo Seong; Ju, So Kyeong; Kim, Wan Ju; (12 pag.)KR101574252; (2015); B1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 87253-62-1, 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.87253-62-1, name is 5,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-carboxylic acid, molecular formula is C8H8N4O2, molecular weight is 192.18, as common compound, the synthetic route is as follows.

General procedure: In 25ml RB flask to a solution of Compound 9 (200 mg) in dry DMF (5ml), EDCI (250 mg, 1.25eq) and DMAP (130 mg,1eq) were added followed by addition of Sulfonamide (1eq). RM was stirred at RT for 4hrs. Solvent from the reaction mixture was evaporated. To the residue water was added and acidified with 6N HCl, solid precipitated out. Solid was filtered and dried. Crude solid was purified by flash chromatography eluating with 4-8% MeOH/DCM as solvent system to give pure product.

Statistics shows that 87253-62-1 is playing an increasingly important role. we look forward to future research findings about 5,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-carboxylic acid.

Reference:
Article; Patil, Vikas; Kale, Manoj; Raichurkar, Anandkumar; Bhaskar, Brahatheeswaran; Prahlad, Dwarakanath; Balganesh, Meenakshi; Nandan, Santosh; Shahul Hameed; Bioorganic and Medicinal Chemistry Letters; vol. 24; 9; (2014); p. 2222 – 2225;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 640769-71-7, 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. 640769-71-7, name is 2-(Pyrimidin-5-yl)benzaldehyde, molecular formula is C11H8N2O, 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.

Tetrabutylammonium fluoride (TBAF, 0.1 ml of 1M in THF) was added to a solution of 2-pyrimidin-5-yl-benzaldehyde (184 mg, 1 mmol) and trifluoromethyl trimethylsilane (TMSCF3, 0.2 ml, 1.2 mmol) in 10 ml THF at 0 C. The mixture was warmed up to room temperature and stirred for 4 hours. The mixture was then treated with 3 ml of 1 M HCl and stirred overnight. The product was extracted with ethyl acetate (3*20 ml). The organic layer was separated and dried over sodium sulfate. The organic solvent was evaporated to give 0.21 g of 2,2,2-trifluoro-1-(2-pyrimidin-5-yl-phenyl)-ethanol (yield: 84%), which was directly used in next step without purification.

According to the analysis of related databases, 640769-71-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Liu, Qingyun; Zambrowicz, Brian; US2009/29993; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 3974-16-1 , The common heterocyclic compound, 3974-16-1, name is 4,6-Dichloro-5-phenylpyrimidine, molecular formula is C10H6Cl2N2, 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.

C. Preparation of 4-chloro-6-(4-chlorophenyl)-5-phenylpyrimidine To a mixture of 4,6-dichloro-5-phenylpyrimidine (675 mg, 3.0 mmol), 4-chlorophenylboronic acid (704 mg, 4.5 mmol) and tetrakis(triphenylphosphine)palladium (173 mg, 0.15 mmol) in toluene (10 mL) at room temperature under argon was added aqueous Na2CO3 solution (2 M, 3 mL, 6 mmol). The resulting reaction mixture was stirred at 100 C. under argon for 5 h, after which time analysis by HPLC/MS indicated that the the reaction was complete. After cooling the reaction mixture to room temperature, water (15 mL) was added. The resulting mixture was extracted with EtOAc (2*25 mL). The combined organic layers were washed with saturated aqueous NaCl, then dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography eluted with ethyl acetate-hexanes to obtain 571 mg of the title compound as a white solid. HPLC/MS: retention time=3.85 min, [M+H]30 =301.

The synthetic route of 3974-16-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wu, Gang; Mikkilineni, Amarendra B.; Sher, Philip M.; Murugesan, Natesan; Gu, Zhengxiang; US2006/287341; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 87253-62-1, Adding some certain compound to certain chemical reactions, such as: 87253-62-1, name is 5,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-carboxylic acid,molecular formula is C8H8N4O2, 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 87253-62-1.

General procedure: In 25ml RB flask to a solution of Compound 9 (200 mg) in dry DMF (5ml), EDCI (250 mg, 1.25eq) and DMAP (130 mg,1eq) were added followed by addition of Sulfonamide (1eq). RM was stirred at RT for 4hrs. Solvent from the reaction mixture was evaporated. To the residue water was added and acidified with 6N HCl, solid precipitated out. Solid was filtered and dried. Crude solid was purified by flash chromatography eluating with 4-8% MeOH/DCM as solvent system to give pure product.

According to the analysis of related databases, 87253-62-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Patil, Vikas; Kale, Manoj; Raichurkar, Anandkumar; Bhaskar, Brahatheeswaran; Prahlad, Dwarakanath; Balganesh, Meenakshi; Nandan, Santosh; Shahul Hameed; Bioorganic and Medicinal Chemistry Letters; vol. 24; 9; (2014); p. 2222 – 2225;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 90856-77-2, 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 90856-77-2 as follows.

3.0 g (7.0 mmol) of Intermediate I-3-2 and 80 ml of toluene were added to a reactor, and then, 0.4 g (3.3 mmol) of 4,6-dimethylpyrimidin-5-amine, 0.1 g (0.5 mmol) of Pd(dba)2, 0.2 g (1.0 mmol) of P(tBu)3, and 0.95 g (9.9 mmol) of sodium butoxide were added thereto. The mixture was then heated and stirred under reflux at a temperature of 120 C. for 36 hours. When the reaction was completed, the resulting mixture was concentrated under reduced pressure, dissolved in dichloromethane, and filtered using diatomite. The organic layer obtained therefrom was dried by using magnesium sulfate to be distilled under reduced pressure, and purified by liquid chromatography to obtain 1.4 g (1.7 mmol, yield: 53%) of Intermediate I-3-1. LC-MS m/z=814 (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,90856-77-2, its application will become more common.

Reference:
Patent; Samsung Electronics Co., Ltd.; CHOI, Jongwon; ARATANI, Sukekazu; LEE, Kum Hee; LEE, Banglin; CHOI, Hyeonho; KWAK, Seungyeon; KWAK, Yoonhyun; KIM, Sangdong; KIM, Jiwhan; BAIK, Chul; CHO, Yongsuk; (115 pag.)US2019/74457; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 98138-75-1, 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 98138-75-1 as follows.

To 6-chloro-4-methoxy-1 H-pyrazolo[3,4-d]pyrimidine (2.45 g) dissolved in dry DMF (60 ml) was added N-iodosuccinimide (3.45 g) and the reaction mixture heated to 80C under stirring. After 3 h the reaction mixture was cooled to RT and the DMF removed by rotary evaporation. Water was added to the residue which was then extracted three times with tert-butyl methyl ether. The combined organic phases were washed with water and brine and dried over sodium sulfate, filtered and evaporated to afford 6-chloro-3-iodo-4-methoxy-1 H-pyrazolo[3,4-d]pyrinnidine as a brown solid. Yield: 4.13 g (100%). MS (ES+): m/e = 310.9 (M+H), chloro pattern

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,98138-75-1, its application will become more common.

Reference:
Patent; SANOFI; NAZARE, Marc; HALLAND, Nis; SCHMIDT, Friedemann; KLEEMANN, Heinz-Werner; WEISS, Tilo; SAAS, Joachim; STRUEBING, Carsten; WO2014/140065; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia