Day: June 1, 2021

Reference of 13479-88-4, 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.13479-88-4, name is 5,7-Dichlorothiazolo[5,4-d]pyrimidine, molecular formula is C5HCl2N3S, molecular weight is 206.0525, as common compound, the synthetic route is as follows.

General procedure: To a solution of 2,4-dichlorofuro[3,2-d]pyrimidine (la) (0.71 g, 3.74 mmol; CAS 956034- 07-4) in 2-Propanol (20 mL) was added DIPEA (1.63 mL, 9.36 mmol), 1-methyl-1H-imidazol-4-amine hydrochloride (0.5 g, 3.74 mmol) and heated at reflux for 24 h. The reaction mixture was concentrated in vacuum to dryness and the residue obtained was triturated with water. The solid obtained was collected by filtration and dried in vacuum to afford 2-chloro-N-(l-methyl-lH-imidazol-4-yl)furo[3,2-d]pyrimidin-4-amine (lb) (550 mg,59 % yield) as brown solid; NMR (300 MHz, DMSO-^) delta 10.89 (s, 1H, D20exchangeable), 8.35 (d, J = 2.1 Hz, 1H), 7.52 (d, J = 1.6 Hz, 1H), 7.39 (d, J = 1.3 Hz, 1H), 7.03 (d, J = 2.1 Hz, 1H), 3.71 (s, 3H); MS (ES+): 250.3 (M+l), 272.3, 274.3 (M+Na), (ES-): 248.2 (M-l).

The chemical industry reduces the impact on the environment during synthesis 13479-88-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; BIOCRYST PHARMACEUTICALS, INC.; KOTIAN, Pravin, L.; BABU, Yarlagadda, S.; KUMAR, V., Satish; ZHANG, Weihe; LU, Peng-Cheng; RAMAN, Krishnan; (747 pag.)WO2018/232094; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 36315-01-2, 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. 36315-01-2, name is 2-Amino-4,6-dimethoxypyrimidine. A new synthetic method of this compound is introduced below.

150 ml round-bottomed Three bottles will amine class Compound (2.0 mmol) and DMAP (2. 5 mmol) was dissolved 10 ml dichloromethane or THF or DMF, at room temperature solution containing 0.43 g 3,4-dichloro-isothiazole carboxylic acid chloride (2.0 mmol) in 2 ml of methylene chloride solution was stirred overnight at room temperature after completion , the reaction mixture was diluted with dichloromethane, washed with water, the organic layer was collected, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give the product after column chromatography, eluted with a volume ratio of 10: 1 petroleum ether: 1-2 : ethyl acetate, with the resulting yield of pure calculation, depending on the yield of the amine range ranging from 16.4% to 88.7%; melting point determination of structural parameters and 1Eta NMR, etc; the chemical structure of the parameters in Table IV

At the same time, in my other blogs, there are other synthetic methods of this type of compound,36315-01-2, 2-Amino-4,6-dimethoxypyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Jiangxi Tianren Ecology Co., Ltd.; Nankai University; Chen, Xiaoyan; Liu, Xiping; Fan, Zhijin; Liang, Xiaowen; Li, Yuedong; Mao, Wutao; Li, Juanjuan; Wang, Dun; Wang, Shuhua; Zhou, Lifeng; Ji, Xiaotian; HUA, XUEWEN; (23 pag.)CN102942565; (2016); B;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 591-55-9, 5-Aminopyrimidine, 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, Recommanded Product: 5-Aminopyrimidine, blongs to pyrimidines compound. Recommanded Product: 5-Aminopyrimidine

A mixture of Pch(dba)3 (7 mg, 0.01 mmol) and BrettPhos (9 mg, 0.02 mmol) in 1,4- dioxane (1 mL) was stirred at 50 C for 10 min. l-(3-chloro-5-methyl-5H-chromeno[4,3- c]pyridin-8-yl)pyrrolidin-2-one (50 mg, 0.16 mmol), pyrimidin-5-amine (18 mg, 0.19 mmol) in dioxane (3 mL) and CS2CO3 (155 mg, 0.476 mmol) were added and the resulting mixture was stirred at 100 C for 16 h. A black brown mixture was formed. LCMS (Rt = 0.605 min; MS Calcd: 373.2; MS Found: 373.9 [M+H]+). The reaction mixture was diluted with DCM (10 mL), filtered and concentrated. The residue was purified by prep-HPLC (0.05% NH32O as an additive) and lyophilized to give l-(5-methyl-3-(pyrimidin-5-ylamino)-5H-chromeno[4,3- c]pyridin-8-yl)pynOlidin-2-one (13.8 mg, yield: 23%) as a white solid. (1160) NMR (400 MHz, DMSO-r/e) d 1.55 (3H, d, J= 6.8 Hz), 2.02-2.09 (2H, m), 2.53 (2H, overlap with DMSO), 3.85 (2H, t , J= 7.6 Hz), 5.31 (1H, q, J= 6.8 Hz), 6.77 (1H, s), 7.33 (1H, dd, J= 8.8, 2.4 Hz), 7.42 (1H, d, J= 2.0 Hz), 7.91 (1H, d, J= 8.4 Hz), 8.72 (1H, s), 8.73 (1H, s), 9.16 (2H, s), 9.64 (1H, brs).

The synthetic route of 591-55-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PETRA PHARMA CORPORATION; KESICKI, Edward A.; LINDSTROeM, Johan; PERSSON, Lars Boukharta; VIKLUND, Jenny; FORSBLOM, Rickard; GINMAN, Tobias; HICKEY, Eugene R.; DAHLGREN, Markus K.; GERASYUTO, Aleksey I.; (391 pag.)WO2019/126730; (2019); 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. 5767-35-1, name is 4-Chloro-6-hydrazinopyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C4H5ClN4

General procedure: To s stirred suspension of the specific 1-(6-chloropyrimidin-4-yl)hydrazine (2) (3.0 mmol) inEtOH (20 mL) was added dropwise an appropriate aldehyde (3.6 mmol, 1.2 equiv) at r. t. over0.5-1 h. The progress of the reaction was monitored by TLC. After completion of the reaction, thesolvent was removed under reduced pressure to afford the crude product. Purification by flashcolumn on silica gel furnished the corresponding pure hydrazone 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, 5767-35-1, 4-Chloro-6-hydrazinopyrimidine.

Reference:
Article; Tang, Caifei; Wang, Chao; Li, Zhiming; Wang, Quanrui; Synthesis; vol. 46; 20; (2014); p. 2734 – 2746;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 425394-89-4, 4,6-Dichloropyrimidin-5-ol, 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, Application In Synthesis of 4,6-Dichloropyrimidin-5-ol, blongs to pyrimidines compound. Application In Synthesis of 4,6-Dichloropyrimidin-5-ol

To a solution of tert-butyl (trans-4-(hydroxymethyl)cyclohexyl)carbamate (0.84 g, 3.65 mmol) in THF (15 mL) was added No.23 triphenylphosphine (1.43 g, 5.45 mmol) and No.23 4,6-dichloropyrimidin-5-ol (0.68 g, 3.65 mmol). To the mixture was added No.23 diisopropylazodicarboxylate (1.47 g, 7.27 mmol) at 0C., the mixture was stirred at room temperature for 18 hr. The reaction mixture was concentrated in vacuo and the residue was purified by column chromatography on silica gel (hexane:ethyl acetate=40:1 as eluent) to afford the tert-butyl (trans-4-(((4,6-dichloropyrimidin-5-yl)oxy)methyl)cyclohexyl)carbamate as colorless oil (0.45 g, 33% yield). LC/MS APCI: Calculated 375.11; Observed m/z [M-99 (boc)]+ 276.1. 1H-NMR 400 MHz, DMSO-d6: delta 8.68 (s, 1H), 6.75 (d, J=7.60 Hz, 1H), 3.94 (d, J=6.00 Hz, 2H), 3.16-3.14 (m, 1H), 1.89-1.79 (m, 4H), 1.73-1.71 (m, 1H), 1.38 (s, 9H), 1.19-1.16 (m, 4H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,425394-89-4, 4,6-Dichloropyrimidin-5-ol, and friends who are interested can also refer to it.

Reference:
Patent; Arrien Pharmaceuticals LLC; Vankayalapati, Hariprasad; US2020/131154; (2020); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 330786-24-8, 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 330786-24-8 as follows.

To 200L reaction kettle adding 124.60 kg tetrahydrofuran, are added under stirring 3 – (4 -)-1H-[34-D]-4-(SM1)(4.00kg1eq)(S)-1-Oxycarbonyl -3 – hydroxy piperidine (SM2) (7.96 kg, 3eq), triphenylphosphine (10.40 kg, 3eq). 25[…] (will be 8.00 kg, 3eq azo-phthalic acid diisopropyl ester soluble in 8.00 kg of in tetrahydrofuran),325(TLCMonitoring: ethyl acetate: methanol=10:1). Stirring under reduced pressure distillation. Temperature control 15 C, dropwise 24.00kg325The reaction is complete (TLC monitoring: dichloromethane: ethyl acetate=5:3). Dichloromethane is used for extraction of the aqueous phase(60.00kg)45.00kgStirring 30 minutes later, the static layering, the minute eliminates upper organic phase. The remaining aqueous phase is added to the 200L anti-1535.00kg 20(9.60Kg sodium hydroxide into 38.40 kg of pure water), the use of pH test paper monitoring reaction solution, pH=5 – 6(2)100LAdding 19.20v ethanol, 0.10 kg of activated carbon, heated to 75 C reflux stirring 2 hours. 1.60kg100LStop heating, water bath cooling, stirring crystallization, when the temperature is reduced to 25 C, thermal crystallization 2 hours. 5.60kg6012Powder 3.75 kg, yield: 85%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,330786-24-8, its application will become more common.

Reference:
Patent; Beijing Rui Chong Kang Tai Pharmaceutical Research Institute Limited; Gu, Huijuan; Chen, Yan; Zhang, Fan; Li, Wei; Liu, Xiangwei; (18 pag.)CN106146512; (2016); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 69034-12-4 ,Some common heterocyclic compound, 69034-12-4, molecular formula is C5H2ClF3N2, 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.

1,1-dimethylethyl(1R,4S,6R)-4-(aminomethyl)-3-azabicyclo[4.1.0]heptane-3-carboxylate D29 (45 mg) was dissolved in DMSO (1 ml) then DIPEA (0.038 ml, 0.219 mmol) and 2-chloro-5-(trifluoromethyl)pyrimidine (36.3 mg, 0.199 mmol) were added and the mixture was stirred at 100 C. for 4 hours. NaHCO3 saturated solution (10 ml) was added and the aqueous layer was extracted with DCM. The combined organic layers were dried over Na2SO4 anhydrous, filtered through a phase separator tube and concentrated under vacuum to give a crude product which was purified by silica gel chromatography (Biotage SP-column size 25 g, using Cy_EtOAc=9:1 to 5:5 as eluent). It was recovered the title compound D32 (45 mg). UPLC: (Acid Final_QC): rt=0.87, peak observed: 373 (M+1). C17H23F3N4O2 requires 372. 1H NMR (400 MHz, CDCl3) delta ppm 8.68-8.28 (m, 2H) 6.23-5.53 (m, 1H) 4.44-3.32 (m, 5H) 1.97-1.73 (m, 2H) 1.52-1.34 (m, 9H) 1.06-0.94 (m, 2H) 0.80-0.64 (m, 1H) 0.27-0.00 (m, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,69034-12-4, its application will become more common.

Reference:
Patent; ALVARO, Giuseppe; Amantini, David; Castiglioni, Emiliano; Di Fabio, Romano; Pavone, Francesca; US2010/144760; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 2915-16-4, 2-Chloro-4,6-diphenylpyrimidine, 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, 2915-16-4, blongs to pyrimidines compound. name: 2-Chloro-4,6-diphenylpyrimidine

A mixture of 2-chloro-4,6-diphenylpryimidine, 0. 79G (2.96 mmol), 4- (HYDROXYLMETHYL) phenylboronic acid, 0.45g (2.96 mmol), Pd (PPh3) 4,342mg (0.296 mmol), in 2 mL of toluene and 1ML of methanol was heated to obtain a clear solution. To the solution was added 2mL of 4. OM aq. NA2CO3. The reaction mixture refluxed for 16h at 70 C. The mixture was cooled to room temperature and diluted with LOOML ethyl acetate. The organic layer was washed with water, sat. aq. NaCl, and dried (MGSO4). After the solution was concentrated, the residue was recrystallized with Et20-Heptane (1 : 1) to afford the desired product in 0.38g (38%) as a yellow SOLID. 1H NMR (DMSO-d6) 8.72 (d, 2H, J = 9. 0HZ), 8.52-8. 47 (m, 4H), 8.45 (s, 1H), 7.64-7. 57 (m, 8H), 4.78 (d, 2H, J = 6.7Hz), 4.37 (t, 1H, J = 6.7Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,2915-16-4, its application will become more common.

Reference:
Patent; THE INSTITUTES FOR PHARMACEUTICAL DISCOVERY, LLC; WO2004/99171; (2004); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 914612-23-0, 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 914612-23-0 as follows.

Alternative synthesis for (S)-3-(6-Benzyl-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-4-yloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester To a solution of (S)-3-hydroxypyrrolidine-1-carboxylic acid tert-butyl ester (6.21 g, 33.16 mmol) and 6-benzyl-4-chloro-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidine (9 g, 34.65 mmol) in 2-Me-THF (100 mL) was added under nitrogen tBuOK (8.17 g, 72.95 mmol). The mixture was stirred at rt for 25 min. The mixture was quenched with H2O. The organic layer was washed with brine. The resulting organic solution was concentrated in vacuo to provide (S)-3-(6-benzyl-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-4-yloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester (12.6 g, 89% yield) as a yellow gum.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,914612-23-0, its application will become more common.

Reference:
Patent; NOVARTIS AG; COOKE, Nigel Graham; FERNANDES GOMES DOS SANTOS, Paulo Antonio; FURET, Pascal; HEBACH, Christina; HOGENAUER, Klemens; HOLLINGWORTH, Gregory; KALIS, Christoph; LEWIS, Ian; SMITH, Alexander Baxter; SOLDERMANN, Nicolas; STAUFFER, Frederic; STRANG, Ross; STOWASSER, Frank; TUFFILLI, Nicola; VON MATT, Anette; WOLF, Romain; ZECRI, Frederic; US2015/342951; (2015); 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. 1197953-49-3, name is (2-((2,5-Dichloropyrimidin-4-yl)amino)phenyl)dimethylphosphine oxide. A new synthetic method of this compound is introduced below., Computed Properties of C12H12Cl2N3OP

Add compound 8a to a 25 mL single-mouth bottle with magnetic stirrer and condenser(760 mg, 3.21 mmol), compound 5a (1.01 g, 3.21 mmol)And ethylene glycol monomethyl ether (10mL), stir and dissolve, add hydrogen chloride isopropanol solution(4.82mmol, 0.96mL, 5M),The temperature was raised to 120 C under a nitrogen atmosphere and stirred to react overnight. Cool to room temperature,Add water (10 mL) and saturated sodium bicarbonate (5 mL) and dichloromethane (15 mL×3)The organic phase was combined, washed with saturated brine and dried over anhydrous sodium sulfate.Filtration, concentration, and residue over silica gel to give a white solid600 mg, the yield was 36.1%.

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, 1197953-49-3, (2-((2,5-Dichloropyrimidin-4-yl)amino)phenyl)dimethylphosphine oxide.

Reference:
Patent; Shenzhen Tajirui Bio-pharmaceutical Co., Ltd.; Wang Yihan; Li Huanyin; (49 pag.)CN109851638; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia