Tag: M.W:100-200

Electric Literature of 31058-83-0 , The common heterocyclic compound, 31058-83-0, name is 6-Chloro-N,N-dimethylpyrimidin-4-amine, molecular formula is C6H8ClN3, 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 mixture ofN-(cis-4-bromo-2-trifluoromethoxy-benzyl)-cyclohexane-1, 4- diamine (466 mg), (6-chloro-pyrimidin-4-yl) -dimethyl-amine (200 mg), and ethylene glycol (0.5 mL) was stirred at reflux for 4 hr in a sealed tube. The mixture was poured into saturated aqueous NaHC03 and the aqueous layer was extracted with CHC13 (three times). The combined organic layer was dried over MgS04, filtered, concentrated under reduced pressure, and purified by flash chromatography (NH-silica gel, 50% EtOAc in hexane and silica gel, 501-‘o MeOH in CHCl3) to give N’- (cis-4- { [4-bromo-2- (trifluoromethoxy) benzyl] amino} cyclohexyl)-N, N-dimethylpyrimidine-4, 6-diamine. To a solution of the above material in EtOAc (2 mL) was added 4 M hydrogen chloride in EtOAc (10 mL). The mixture was stirred at ambient temperature for 1 hr and concentrated under reduced pressure. The residue was suspended in Et2O (20 mL) and the suspension was stirred at ambient temperature for 4 hr. The precipitate was collected by filtration, washed with Et2O, and dried under reduced pressure to give N’-(cis-4-{[4-bromo-2- (trifluoromethoxy) benzyl] amino} cyclohexyl)-N,N-dimethylpyrimidine-4, 6-diamine dihydrochloride (67 mg). ESI MS m/e 488, M (free) + H+ ;’H NMR (300 MHz, CDC13) 8 1.64-1. 86 (m, 2 H), 1.96- 2.34 (m, 8 H), 2. 98-3.44 (m, 8 H), 4.27 (s, 2 H), 7.40-7. 59 (m, 3 H), 8.06-8. 24 (m, 2 H).

The synthetic route of 31058-83-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAISHO PHARMACEUTICAL CO., LTD.; Arena Pharmaceuticals, Inc; WO2005/95357; (2005); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 1004-39-3 ,Some common heterocyclic compound, 1004-39-3, molecular formula is C4H6N4S, 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.

EB1 Schiff base was synthesized by reaction of 30mL of ethanol hot solution (60 C) of bisaldehyde (2,2?-(ethane-1,2-diylbis(oxy))dibenzaldehyde) (1 g, 3.7¡Á10-3mole) and 30 mL hot ethanol solution (60 C) of (hydrazine carbothioamide) (0.674 g, 7.4¡Á10-3mole) in ratio (1:2). In preparation of L1 Schiff base 30 mL of ethanol hot solution (60 C) of bisaldehyde (2,2?-(ethane-1,2-diylbis(oxy))dibenzaldehyde) (1 g, 3.7¡Á10-3mole) was mixed with 30 mL hot ethanol solution (60 C) (4,6-diaminopyrimidine-2-thiol) (0.525 g, 3.6¡Á10-3mole) in ratio (1:1). Then sulfuric acid was added to eliminate water through condensation, and then the reaction mixture was left under reflux for 2 h. The formed solid Schiff?s bases were separated by filtration and purified by crystallization from ethanol. This preparation can be summarized in the following Scheme 1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1004-39-3, its application will become more common.

Reference:
Article; Zayed, Ehab M.; Zayed; El-Desawy; Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy; vol. 134; (2015); p. 155 – 164;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 39906-04-2 ,Some common heterocyclic compound, 39906-04-2, molecular formula is C5H5Cl2N3, 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 mixture of 4,6-dichloro-2-methylpyrimidin-5amine(1 g, 5.62 mmol) and O-ethyl carbonisothiocyanatidate(0.66 ml., 5.62 mmol) was added toluene (2 mL) to wet thesolids completely. The mixture was placed on 1000 C. oil bathfor 1.5 hours, at which time, the mixture had seized to give asolid mass. The solids were cooled to ambient temperatureand triturated with ether, then the resulting solids were collectedby filtration to give ethyl 7-chloro-5-methylthiazolo[5,4-d]pyrimidin-2-ylcarbamate (1.08 g, 3.96 mmol, 70.5%yield).

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. 39906-04-2, 4,6-Dichloro-2-methylpyrimidin-5-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; COOK II, JAMES H; MCDONALD, IVAR M; KING, DALTON; OLSON, RICHARD E; WANG, NENGHUI; IWUAGWU, CHRISTIANA I; ZUSI, F.CHRISTOPHER; MACOR, JOHN E; (330 pag.)JP5714745; (2015); B2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 5305-40-8, 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.5305-40-8, name is 4,6-Dichloropyrimidine-5-carbaldehyde, molecular formula is C5H2Cl2N2O, molecular weight is 176.9882, as common compound, the synthetic route is as follows.

Preparation of 4-Chloro-1H-pyrazolo[3,4-d]pyrimidine: 4,6-Dichloro-pyrimidine-5-carbaldehyde hydrazine (10 mL, excess), and dioxane (90 mL) are combined at -78 C. in THF. The reaction solution is warmed to rt and stirred for 16 hr. The solvent is evaporated in vacuo to provide a crude residue which is diluted with dichloromethane (600 mL). The organic solution is washed with water (50 mL), brine (50 mL) and dried over anhydrous sodium sulfate. The solvent is removed in vacuo to provide 4-Chloro-1H-pyrazolo[3,4-d]pyrimidine as a yellow powder which is used without further purification.

The chemical industry reduces the impact on the environment during synthesis 5305-40-8, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ChemoCentryx, Inc.; US2007/10523; (2007); 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. 4595-61-3, name is Pyrimidine-5-carboxylic acid, the common compound, a new synthetic route is introduced below. name: Pyrimidine-5-carboxylic acid

To a solution of pyrimidine-5-carboxylic acid (1.38 g, 11.13 mmol, 1.1equiv; [CAS RN 4595-61-3]) in DMF (44 mL) was added 3-(4-trifluoromethyl-phenyl)-prop-2-yn-1-ol(2.02 g, 10.1 mmol, 1.0 equiv; [CAS RN 173546-21-9]), 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide) hydrochloride (2.33 g, 12.1 mmol, 1.2 equiv; [CASRN 25952-53-8]) and 4-dimethylaminopyridine (0.25 g, 2.0 mmol, 0.2 equiv). The reaction mixturewas stirred at rt for 2 h and then concentrated by evaporation under reducedpressure. A sat. solution of NaHCO3 (50 mL) was added and the crude productextracted with DCM (3 x 100 mL). The combined organic layers were dried over MgSO4,concentrated under reduced pressure and the product purified by MPLC elutingwith a gradient of DCM / methanol. The title compound was isolated as whitesolid (2.36 g, 76percent).?1H NMR (600 MHz, CDCl3): d = 5.23 (s, 2H), 7.57 ? 7.60 (m, 4H), 9.35 (s, 2H), 9.41 (s, 1H). 13CNMR (150 MHz, CDCl3): d = 54.0, 84.5, 86.1, 123.9 (q, JCF= 270.6 Hz), 123.9 (br s), 125.5 (q, JCF= 3.7 Hz), 125.7 (d, JCF =1.4 Hz), 131.0 (q, JCF =32.6 Hz), 132.3, 158.3, 161.9, 163.1. 19F NMR (280MHz, CDCl3): d = -63.0. HRMS (ESI+): m/z [M]+ calcd for C15H9F3N2O2:306.0616, found: 306.0610.

The synthetic route of 4595-61-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Martin, Rainer E.; Lenz, Mario; Alzieu, Thibaut; Aebi, Johannes D.; Forzy, Liliane; Tetrahedron Letters; vol. 54; 49; (2013); p. 6703 – 6707;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 20781-06-0, 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. 20781-06-0, name is 2,4-Diaminopyrimidine-5-carboxaldehyde. A new synthetic method of this compound is introduced below.

A mixture of 0.188 g (1 mmol) of compound of formula V and 0.447 g (1.5 mmol) of compound of formula III-1, 0.126 g (2 mmol) of sodium cyanoborohydride was added and maintained in a reflux state for 24 hours in 15 mL of methanol, The water was washed with ethyl acetate and the organic phase was washed with saturated brine and the organic phase was concentrated (the solvent was removed under reduced pressure). The residue was purified by silica gel column chromatography (Eluent: methanol: dichloromethane = 1: 10, v / v) to give a white solid (IB-1) The yield was 78%

At the same time, in my other blogs, there are other synthetic methods of this type of compound,20781-06-0, 2,4-Diaminopyrimidine-5-carboxaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; East China University of Science and Technology; Zhu Jin; Huang Jin; Chen Wenhua; Yao Xue; Ling Dazheng; Wang Manjiong; Jiang Hualiang; Li Jian; (21 pag.)CN106938997; (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. 93366-88-2, name is 7H-Pyrrolo[2,3-d]pyrimidin-2-amine. This compound has unique chemical properties. The synthetic route is as follows. category: pyrimidines

7H-pyrrolo[2,3-d]pyrimidin-2-amine (160 mg, 1.19 mmol), 3-bromo-5-iodopyridine (676 mg, 2.39 mmol),potassium carbonate (493 mg, 3.57 mmol) and proline(28 mg, 0.24 mmol) was added to an eggplant flask, dimethyl sulfoxide was added, and the reaction solution was deoxidized. Copper iodide (23 mg, 0.12mmol) was added and the reaction solution was deoxygenated. Heat to 90 C and stir for 16 hours. After the reaction was completed, it was cooled to room temperature, water and ethyl acetate were added, and the mixture was filtered over celite. The target compound was obtained in 24 mg.

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, 93366-88-2, 7H-Pyrrolo[2,3-d]pyrimidin-2-amine.

Reference:
Patent; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Zhao Yujun; Li Zhiqiang; Yan Ziqin; Li Jia; Zhou Yubo; Su Mingbo; Chen Zheng; (138 pag.)CN109810110; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 29274-22-4, 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. 29274-22-4, name is Pyrazolo[1,5-a]pyrimidin-5-ol. A new synthetic method of this compound is introduced below.

A mixture of the product (1.35 g, 10.0 mmol) from Step A above and 7.5 mL of phosphorus oxychloride was warmed at reflux for 4 h. The mixture was cooled, and the volatiles were removed under reduced pressure. The dark residue was partitioned between ice water and dichloromethane, and the aqueous layer was extracted with additional dichloromethane. The combined organic extracts were dried over sodium sulfate and concentrated under reduced pressure to provide a light brown solid, which was purified by flash chromatography (silica gel; 0.5% methanol in dichloromethane eluant) to afford the title compound as a white solid. MS 153.8 and 155.8 (M+1).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,29274-22-4, Pyrazolo[1,5-a]pyrimidin-5-ol, and friends who are interested can also refer to it.

Reference:
Patent; MERCK & CO., INC.; WO2004/43940; (2004); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 111196-81-7 ,Some common heterocyclic compound, 111196-81-7, molecular formula is C6H7ClN2, 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 screw-cap vial was charged with benzamide (121 mg, 1.00 mmol), Cs2CO3 (456 mg, 1.40 mmol), Xantphos (87 mg, 0.15 mmol), Pd2(dba)3 (46 mg, 0.050 mmol), 2-chloropyrimidine (137 mg, 1.20 mmol), and 1,4-dioxane (2 mL). The mixture was sparged with nitrogen for 3 min, stirred for 16 h at 100 C, and cooled to room temperature. The residue was diluted with dichloromethane, filtered through celite, and concentrated. The crude product was purified by silica gel flash chromatography (40-100% ethylacetate/hexanes) to provide N-(pyrimidin-2-yl)benzamide (188 mg, 0.85 mmol, 94% yield) as an amorphous solid (Table 1, entry 8).

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. 111196-81-7, 2-Chloro-5-ethylpyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Vimolratana, Marc; Simard, Jillian L.; Brown, Sean P.; Tetrahedron Letters; vol. 52; 9; (2011); p. 1020 – 1022;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 3993-78-0, 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 3993-78-0, name is 2-Amino-4-chloropyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

A microwave vial was charged with 2-amino-4-chloropyrimidine (2.0 g, 15.4 mmol), and pyrrolidine (10 mL) was added. The vial was sealed, and heated in the microwave at 150 C for 1 h. After cooling, the reaction was diluted with methanol (30 mL), and silica (15 g) was added. All solvents were removed in vacuo, and the remaining silica slurry loaded on a 40.0 g silica column. Elution with a 0% to 10% methanol in dichloromethane gradient yielded 4-(pyrrolidin-1-yl)pyrimidin-2-amine (1.70 g, 67% yield). MS (ESI) calcd for C8H14N4: 164.11

According to the analysis of related databases, 3993-78-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SIRTRIS PHARMACEUTICALS, INC.; CASAUBON, Rebecca, L.; NARAYAN, Radha; OALMANN, Christopher; VU, Chi, B.; WO2013/59587; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia