Tag: M.W:100-200

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.56741-94-7, name is 2-Amino-6-phenylpyrimidin-4(3H)-one, molecular formula is C10H9N3O, molecular weight is 187.2, as common compound, the synthetic route is as follows.Formula: C10H9N3O

Intermediate 1A : Preparation of 4-chloro-6-phenylpyrimidin-2-amine; A suspension of guanidine carbonate (3.60 g, 20 mmol) in ethanol (120 mL) and toluene (20 mL) was refluxed under nitrogen for 1 h, during which time about 50 mL of solvent was removed by distillation. After the mixture was cooled to 45 C, ethyl 3-oxo-3- phenylpropanoate (7.68 g, 40 mmol) was added and the solution was heated at reflux overnight. The desired product precipitated as a white solid during the reaction. Water (50 mL) was added to the reaction and the mixture was refluxed for an additional 30 min. After cooling to rt, the mixture was neutralized with 1N HC1 and placed in the refrigerator for 6 h. The solid was filtered, washed with water followed by ether and dried at 60 C under vacuum to give the product as white solid (6.45 g, 86%). MS ES: 188 (M+H) +, calcd 188; RT = 0.91 min; TLC (CH2C12/2M NH3 in MeOH 95/5) Rf = 0.10. A mixture of the above product (6.0 g, 32 mmol) and POC13 (100 mL) was heated at reflux for 1 h. The majority of the POC13 was removed in vacuo and the residue was diluted with EtOAc and poured over an ice/saturated NaHC03 solution. The aqueous layer was extracted with EtOAc and the combined organic layers were washed with brine, dried (Na2SO4), and concentrated. The crude organic concentrate was re-crystallized from EtOAc/ether to give the product 1A as an off-white powder (2. 8 g, 43%). MS ES: 206 (M+H) +, calcd 206; RT = 2.49 min; TLC (CH2C12/2M NH3 in MeOH 95/5) Rf = 0.72. (Reference 1: H. L. Skulnick, S. D. Weed, E. E. Edison, H. E. Renis, W. Wierenga, and D. A. Stringfellow, J ; Med. Cllem. 1985, 28,1854-1869).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,56741-94-7, 2-Amino-6-phenylpyrimidin-4(3H)-one, and friends who are interested can also refer to it.

Reference:
Patent; BAYER PHARMACEUTICALS CORPORATION; WO2005/35507; (2005); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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.90349-23-8, name is 5,7-Dimethylpyrazolo[1,5-a]pyrimidine-3-carboxylic acid, molecular formula is C9H9N3O2, molecular weight is 191.19, as common compound, the synthetic route is as follows.Application In Synthesis of 5,7-Dimethylpyrazolo[1,5-a]pyrimidine-3-carboxylic acid

General procedure: To a stirred solution of carboxylic acid compound (1.0 equivalent), HATU (1.5 equivalents), and DIPEA (3.75 equivalents) in DCM or DMF (~4 mL/0.2 mmol) was added amine compound (1.25 – 2.0 equivalents). The reaction mixture was stirred at roomtemperature for 4-16 hours, and then washed with saturated aqueous aHC03solution (5 mL/0.2 mmol), aqueous citric acid solution (5 mL/0.2 mmol) and brine (5 mL/0.2 mmol). The combined extracts were dried over anhydrous a2S04, filtered and concentrated in vacuo. The resulting crude material was purified by silica gel column chromatography or preparatory HPLC to give the amide compound. Following general procedure A, 5,7-dimethylpyrazolo[l,5-a]pyrimidine-3- carboxylic acid (40 mg, 0.21 mmol) and 1,2,3,4-tetrahydronaphthalen-l -amine afforded the title compound (37 mg, 55%) as a yellow solid.XH NMR (500 MHz, CDC13): delta 8.68 (s,1H),8.42 (d, J= 8.5 Hz, 1H), 7.47 (d, J= 7.0 Hz, 1H), 7.18-7.13 (m, 3H), 6.67 (s, 1H), 5.52- 5.49 (m, 1H), 2.91-2.84 (m, 2H), 2.78 (s, 2H), 2.53 (s, 3H), 2.25-2.22 (m, 1H), 2.00-1.90 (m, 3H). LC-MS m/z: 321.2 [M+H]+. HPLC Purity (214 nm): > 99 %; tR= 8.26 min.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,90349-23-8, 5,7-Dimethylpyrazolo[1,5-a]pyrimidine-3-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; LYSOSOMAL THERAPEUTICS INC.; SKERLJ, Renato, T.; LANSBURY, Peter, T.; GOOD, Andrew, C.; BOURQUE, Elyse, Marie Josee; (139 pag.)WO2016/73895; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 4316-97-6, 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. 4316-97-6, name is 4,6-Dichloro-5-methylpyrimidine, molecular formula is C5H4Cl2N2, 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 4,6-dichloro-5-methylpyrimidine (1.00 g, 6.13 mmol) in MeOH (50 mL) at 0C was added solid sodium methoxide (0.348 g, 6.44 mmol) in portions. The reaction mixture was allowed to warm to room temperature and stirred at room temperature for 4 hours and then at 500C for 12 hours. Additional sodium methoxide (0.348 g, 6.44 mmol) was added and the reaction mixture was stirred at 50C for 4 hours. Additional sodium methoxide (0.348 g, 6.44 mmol; 3 eq total) was added and the reaction mixture was stirred at 5O0C for 20 minutes, when HPLC showed the reaction was complete. The reaction mixture was concentrated and then partitioned between EtOAc and saturated aqueous NH4Cl. The phases were separated, and the aqueous phase was re- extracted with EtOAc (Ix). The combined organic layers were dried (Na2SO4), filtered and concentrated to yield the desired product (0.829 g, 85%) as a colorless oil that was used without further purification. 1H-NMR (400 MHz, CDCl3) delta 8.42 (s, IH), 4.02 (s, 3H). LRMS (ESI pos) m/e l59 (M+l).

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 4316-97-6, 4,6-Dichloro-5-methylpyrimidine.

Reference:
Patent; ARRAY BIOPHARMA INC.; GENENTECH, INC.; WO2007/146824; (2007); A2;,
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. 49845-33-2, name is 2,4-Dichloro-5-nitropyrimidine. This compound has unique chemical properties. The synthetic route is as follows. category: pyrimidines

Following the preparation protocol of Section 5.1.2.1, the reaction mixtureof 2,4-dichloro-5-nitropyrimidine (1a) (250 mg, 1.29 mmol),DIEA (0.22 mL, 1.29 mmol) and aniline (120 mg, 1.29 mmol) inDCM (1 mL) was stirred at 0 C for 5 min to give the title compound2q as a yellow solid (277 mg, 85.8percent); mp 171?173 C; 1H NMR(400 MHz, DMSO d6) d (ppm) 10.45 (s, 1H), 9.16 (s, 1H), 7.54 (d,J = 8.0 Hz, 2H), 7.45 (t, J = 7.6 Hz, 2H), 7.29 (t, J = 7.2 Hz, 1H); 13CNMR (100 MHz, CDCl3) d (ppm) 164.26, 157.60, 153.44, 135.45,129.30, 126.65, 122.85; HRMS (ESI): m/z, Calcd. for C10H8O2N4Cl[M+H]+: 251.0330, Found 251.0329.

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, 49845-33-2, 2,4-Dichloro-5-nitropyrimidine.

Reference:
Article; Cui, Guonan; Jin, Jing; Chen, Hualong; Cao, Ran; Chen, Xiaoguang; Xu, Bailing; Bioorganic and Medicinal Chemistry; vol. 26; 8; (2018); p. 2186 – 2197;,
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. 14048-15-8, name is 2,4-Dimethoxypyrimidin-5-amine, the common compound, a new synthetic route is introduced below. name: 2,4-Dimethoxypyrimidin-5-amine

2,4-Dimethoxypyrimidin-5-amine (0.1 g) was dissolved in dry dichloromethane (5 mL)and pyridine (1 mL) and to this was added /’so-butylchloroformate (0.11 mL). Theresulting mixture was stirred at room temperature for 1 hour and was then poured into INhydrochloric acid and extracted into dichloromethane (2 x lOmL), dried (MgSO4), filteredand concentrated. The residue was dissolved in dry 1,2-dimethoxyethane (5 mL) andsodium hydride (60%, 0.032g) was added, followed by 2,3-dichlorobenzenesulphonylchloride (0.196 g). The reaction was stirred for 1 hour, poured into water and extractedinto ethyl acetate (2 x lOmL) and concentrated. The residue was dissolved in methanol (5mL) and IN sodium hydroxide (5 mL) added. The mixture was heated to reflux for 1hour, cooled and concentrated to 5 mL, acidified by the addition of 2N hydrochloric acidand extracted into ethyl acetate, dried (MgSO4), filtered and concentrated. The residue waspurified by chromatography on silica gel eluting with ethyl acetate /wo-hexanes (1/2) toafford the titled compound as a solid

The synthetic route of 14048-15-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; WO2004/108690; (2004); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 1683-85-8 , The common heterocyclic compound, 1683-85-8, name is 5-Fluoropyrimidin-2-amine, molecular formula is C4H4FN3, 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 suspension of 5-chloro-2,4-difluorobenzenesulfonyl chloride (1 .99 g, 8.05 mmol) in dichloromethane (15 ml_) was added portion-wise to a solution of 5-fluoro-pyrimidin-2- ylamine (1 .00 g, 8.84 mmol) in pyridine (15 ml_) at 0 C. The reaction mixture was then allowed to warm to ambient temperature gradually and stirred for 1 6 hours. The reaction mixture was diluted with dichloromethane and partitioned with 1 N aqueous hydrogen chloride solution. The layers were separated and the aqueous layer extracted with dichloromethane. The combined organic layers were washed with water, diluted with ethyl acetate, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by automated silica gel column chromatography (100% chloroform to 10% methanol in chloroform gradient elution) to afford the title compound as a light yellow solid (0.32 g).1HNMR (de-DMSO): delta 7.85 (m, 1 H), 8.17 (m, 1 H), 8.67 (s, 2H).LCMS Rt = 1 .53 min MS m/z 324 [MH]+

The synthetic route of 1683-85-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER LIMITED; ICAGEN, INC.; MARKWORTH, Christopher John; MARRON, Brian Edward; RAWSON, David James; STORER, Robert Ian; SWAIN, Nigel Alan; WEST, Christopher William; ZHOU, Shulan; WO2012/4706; (2012); A2;,
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. 17573-78-3, name is 4,5,6-Trifluoropyrimidine, the common compound, a new synthetic route is introduced below. category: pyrimidines

[00339] 11.38 g (0.085 mol) of trifluoropyrimidine are dissolved in 240 ml of acetonitrile and admixed with 15.26 g (0.11 mol) of potassium carbonate, and the mixture is cooled to 10 C. Under argon, a solution of 9.52 g (0.085 mol) of 3-fluorophenol in 80 ml of acetonitrile is added dropwise. The mixture is then stirred under argon, without further cooling, for another 18 hours. The mixture is poured into 1 litre of water and extracted three times with in each case 150 ml of ethyl acetate, and the organic phase is dried over sodium sulphate and concentrated under reduced pressure. The residue is subjected to kugelrohr distillation. This gives 15.2 g (79.1% of theory) of 5,6-difluoro-(3-fluorophenoxy)-pyrimidine of boiling point 95 C. at 0.5 mbar.

The synthetic route of 17573-78-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bayer Aktiengesellschaft; US6683029; (2004); B1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 56621-98-8, 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. 56621-98-8, name is 5-Aminopyrimidine-2-carboxylic acid, molecular formula is C5H5N3O2, 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.

A suspension of 5-aminopyrimidine-2-carboxylic acid (Goldenbridge Pharma, Inc.; 5.70 g, 41.0 mmol) in MeOH (120 mL) was cooled in an ice-water bath and treated dropwise with thionyl chloride (8.97 mL, 123 mmol). The resulting suspension was heated at reflux for 20 h and then concentrated to give a yellow solid. The solid was dissolved in saturated aqueous NaHC03 (60 mL) and extracted into EtOAc using a Gregar Extractor. The extract was concentrated to give methyl 5-aminopyrimidine-2- carboxylate (4.26 g, 68 % yield) as an off-white solid. H NMR (400 MHz, CDCl3): delta 8.32 (s, 2H), 4.35 (br s, 2H), 4.02 (s, 3H)

According to the analysis of related databases, 56621-98-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AMGEN INC.; MINATTI, Ana Elena; LOW, Jonathan, D.; ALLEN, Jennifer, R.; AMEGADZIE, Albert; BROWN, James; FROHN, Michael, J.; GUZMAN-PEREZ, Angel; HARRINGTON, Paul, E.; LOPEZ, Patricia; MA, Vu Van; NISHIMURA, Nobuko; QIAN, Wenyuan; RUMFELT, Shannon; RZASA, Robert, M.; SHAM, Kelvin; SMITH, Adrian, L.; WHITE, Ryan; XUE, Qiufen; WO2014/138484; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 56621-90-0, 5-Amino-2-chloropyrimidine, 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: 56621-90-0, blongs to pyrimidines compound. SDS of cas: 56621-90-0

A mixture of the pyrimidine from step 4 (100 mg, 0.77 mmol), indole boronic acid from step 3 (290 mg, 0.77 mmol), Pd(dppf)Cl2 (56 mg, 0.077 mmol), Na2CO3 (244 mg, 2.3 mmol), THF (20 mL) and H2O (2 mL) was refluxed under N2 overnight. The mixture was poured into water and extracted with CH2Cl2. The organic phase was combined, dried over Na2SO4 and filtered. The filtrate was purified by prep TLC (CH2Cl2/MeOH=20/1) to afford the product. MS (ESI) m/e (M+H+): 426.

The synthetic route of 56621-90-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck Sharp & Dohme Corp.; Coburn, Craig A.; Ludmerer, Steven W.; Liu, Kun; Wu, Hao; Soll, Richard; Zhong, Bin; Zhu, Jian; (155 pag.)US2019/127365; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 1005-37-4, name is 6-Chloro-N4-methylpyrimidine-2,4-diamine, molecular formula is C5H7ClN4, 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. HPLC of Formula: C5H7ClN4

Example 2606-(4-fluoro-2,3-dimethylphenyl)-4-N-methylpyrimidine-2,4-diamine.A mixture of 6-chloro-4-N-methylpyrimidine-2,4-diamine (24 mg, 0.15 mmol), (4-fluoro-2,3-dimethylphenyl)boronic acid (30 mg, 0.18 mmol), potassium carbonate(41 mg, 0.30 mmol) and tetrakis(triphenylphosphine)palladium (0) (9 mg, 0.008mmol) in 1 ,4-dioxane (3 mL) and water (1 mL) was heated in a sealed tube at90C overnight. The reaction mixture was concentrated and purified bypreparative H PLC. LCMS [M+H] 247.

With the rapid development of chemical substances, we look forward to future research findings about 1005-37-4.

Reference:
Patent; THOMAS HELLEDAYS STIFTELSE FOeR MEDICINSK FORSKNING; SCOBIE, Martin; HELLEDAY, Thomas; KOOLMEISTER, Tobias; JACQUES, Sylvain; DESROSES, Matthieu; JACQUES-CORDONNIER, Marie-Caroline; WO2014/84778; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia