Pyrimidines

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. 5909-24-0, name is Ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate. A new synthetic method of this compound is introduced below., Application In Synthesis of Ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate

To 600ml of methylene dichloride was added lOOg of ethyl 4-chloro-2-(methylsulfanyl) pyrimidine-5-carboxylate and 91.2g of 3-chloro-4-methoxybenzylamine. The reaction mixture was stirred and 500m1 of water, 48g of sodium carbonate and Ig of tetra-butylammonium bromide were added to it. The reaction mixture was then maintained overnight at 25-30C. After completion of reaction, methylene dichloride layer was separated, washed with water and evaporated to obtain 145g of ethyl 4-[(3-chloro-4-methoxybenzyl) amino]-2-(methyl sulfanyl) pyrimidine-5-carboxylate having 95% of HPLC purity.

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, 5909-24-0, Ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate.

Reference:
Patent; WANBURY LTD.; NITIN SHARADCHANDRA PRADHAN; VIHAR RAGHUNATH TELANGE; SURYAKANT SHIVAJI POL; SHASHIKANT BALU PADWAL; NITN SHANKAR BONDRE; WO2015/177807; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 108381-28-8, 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. 108381-28-8, name is 4-(Benzyloxy)-2-chloropyrimidine, molecular formula is C11H9ClN2O, 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.

Step 1 In a microwave vial, cis-7-methyl-8-((3,4,5-trifluorophcnyl)carbamoyl)-2,3,3a,4,10,10a-hexahydro-lH,7H-dipyrrolo[3,4-b:3′,4′-f][l,4,5]oxathiazocin-2-ium 5,5-dioxide iodide (E11) (30 mg, 0.054 mmol) and 4-(benzyloxy)-2-chloropyrimidine (24 mg, 0.109 mmol) were suspended in 1-Butanol (0.5 mL), dry DIPEA (0.030 mL, 0.172 mmol) was added and mixture was heated at l20C under MW heating for lh. UPLC-MS showed complete conversion. The mixture was evaporated under reduced pressure to afford a brown solid. The residue was purified by preparative HPLC (H20, CEbCN 0.1% TFA) to afford, after lyophilization, 2-(4-(benzyloxy)pyrimidin-2-yl)-7-methyl-N-(3,4,5-trifluorophenyl)-2,3,3a,4,l0,l0a-hexahydro-lH,7H-dipyrrolo[3,4-b:3′,4′-f][l,4,5]oxathiazocine-8-carboxamide 5,5-dioxide as a beige powder (30 mg, yield=9l%). 4-(benzyloxy)-2-chloropyrimidine was present as impurity. Product was used in next step without further purification.

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 108381-28-8, 4-(Benzyloxy)-2-chloropyrimidine.

Reference:
Patent; OSPEDALE SAN RAFFAELE S.R.L.; IRBM S.P.A.; PROMIDIS S.R.L.; ISTITUTO NAZIONALE DI GENETICA MOLECOLARE – INGM; DE FRANCESCO, Raffaele; DONNICI, Lorena; GUIDOTTI, Luca; IANNACONE, Matteo; DI FABIO, Romano; SUMMA, Vincenzo; PRANDI, Adolfo; RANDAZZO, Pietro; GORNATI, Davide; GRILLO, Alessandro; FERRANTE, Luca; BENCHEVA, Leda Ivanova; DE MATTEO, Marilenia; FERRARA, Marco; (238 pag.)WO2020/30781; (2020); 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. 56-09-7, name is 2-Amino-6-hydroxypyrimidin-4(3H)-one, the common compound, a new synthetic route is introduced below. Formula: C4H5N3O2

General procedure: Typically, 2-aminopyrimidine-4,6-diol (1a, 0.5 mmol, 1.0 equiv)/2-methylpyrimidine-4,6-diol (1b, 0.5 mmol, 1.0 equiv), nitroolefins (2, 0.5 mmol, 1.0 equiv), as well as water (2.5 mL) were introduced into a 10 mL reaction vial. Then, the reaction vial was closed and stirred for given time at 90 C. Upon completion, the reaction mixture was cooled to room temperature and diluted with cold water (30 mL). The solid product was collected by filtration and was purified by recrystallization from hot 95% EtOH to afford the goal product 5-arylfuro[2,3-d]pyrimidin-4-ol (3) as off-white to yellow solid. 2-Amino-6-methyl-5-phenylfuro[2,3-d]pyrimidin-4-ol (3a) Light yellow solid; Mp: >300 C; 1H NMR (400 MHz, DMSO-d6): delta = 10.82 (br, s, 1H, OH), 7.50 (d, J = 7.2 Hz, 2H, ArH), 7.39 (t, J = 7.6 Hz, 2H, ArH), 7.28-7.31 (m, 1H, ArH), 6.63 (br, s, 2H, NH2), 2.32 (s, 3H, CH3); 13C NMR (100 MHz, DMSO-d6): delta = 167.3, 158.9, 154.3, 143.0, 131.9, 130.0, 128.2, 127.1, 117.7, 96.4, 12.6; HRMS (ESI): m/z [M+H]+ calcd for C13H12N3O2 + : 242.0924; found: 242.0929.

The synthetic route of 56-09-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Li, Chunmei; Zhang, Furen; Tetrahedron Letters; vol. 58; 16; (2017); p. 1572 – 1575;,
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Pyrimidine – Wikipedia

Application of 934524-10-4, 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 934524-10-4 as follows.

To a solution of 3-propylthiophene (1.3 g, 10 mmol) in anhydroud THF (25 rnL) cooled at -78 0C under argon atmosphere was added ra-BuLi (2.5 M in hexanes; 4.4 mL, 11 mmol). The mixture was stirred at the same temperature for 15 min and trimethyllborate added (2.2 mL, 20 mmol). The resulting mixture was stirred at at -78 0C for 15 min and then stirred at RT for 2 h. The reaction was quenched with IM HCl (3 mL) and concentrated. The residue was taken up in water (40 mL) and extracted with EtOAc (2 x 40 mL). The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated and the crude product purified by silica gel column (CHCl3 to 10% CH3OH/CHCI3) to afford 4-propylthiophen-2-yl-2-boronic acid as an off-white solid (0.5 g, 29%). A mixture of 8 (0.28 g, 0.82 mmol), 4-propylthiophen-2-yl-2-boronic acid (0.17 g, 1.0 mmol), Pd(PPh3)4 (96 mg, 0.08 mmol) and Na2CO3 (0.32 g, 3 mmol) in anhydrous DMF (10 mL) was degassed with argon for 2 min and then heated at 120 0C in a sealed tube for 2 h. After cooling to room temperature, the solvent was removed by rotovap. The crude product was then purified by silica gel column with 1 : 1 hexanes/CHCl3 as an eluent to yield a yellow solid (90 mg, 25%).[0346] 1H NMR (500 MHz, CDCl3): delta 0.96 (t, J = 7.4 Hz, 3H), 1.60-1.75 (m, 2H), 2.42 (s, 3H), 2.63 (t, J = 1.6 Hz, 2H), 6.95 (d, J = 4.0 Hz, IH), 7.22 (s, IH), 7.74 (d, J = 4.2 Hz, IH), 7.79 (s, IH), 8.13 (d, J = 8.4 Hz, 2H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,934524-10-4, its application will become more common.

Reference:
Patent; TARGEGEN INC.; WO2009/49028; (2009); A1;,
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Pyrimidine – Wikipedia

Application of 1445-39-2, Adding some certain compound to certain chemical reactions, such as: 1445-39-2, name is 2-Amino-5-iodopyrimidine,molecular formula is C4H4IN3, 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 1445-39-2.

h) 7-(N-(3-((2-aminopyrimidin-5-yl)ethynyl)-2,4-difluorophenyl) sulfamoyl)-5-chloro-2,3-dihydrobenzofuran-3-yl Acetate A mixture of 5-chloro-7-(N-(3-ethynyl-2,4-difluorophenyl)sulfamoyl)-2,3-dihydrobenzofuran-3-yl acetate (290 mg), dichlorobis(tricyclohexylphosphine)palladium(II) (50.0 mg), DIPEA (2 mL), copper(I) iodide (25.8 mg), 5-iodopyrimidin-2-amine (195 mg) and DMSO (3 mL) was stirred under microwave irradiation at 100 C. for 1 hr. After cooling to room temperature, the reaction mixture was diluted with water and extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over magnesium sulfate and concentrated to give a residue. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (254 mg). MS: [M-H]- 519.1.

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. 1445-39-2, 2-Amino-5-iodopyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Takeda Pharmaceutical Company Limited; FUJIMOTO, Jun; LIU, Xin; KURASAWA, Osamu; TAKAGI, Terufumi; CARY, Douglas Robert; BANNO, Hiroshi; ASANO, Yasutomi; KOJIMA, Takuto; (159 pag.)US2019/169166; (2019); A1;,
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Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 4359-87-9, 2,4,6-Trichloro-5-nitropyrimidine, 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, 4359-87-9, blongs to pyrimidines compound. Recommanded Product: 4359-87-9

b) 4-(2,6-Dichloro-5-nitropyrimidin-4-yl)morpholine A solution of morpholine (0.362 g, 4.2 mmol) and triethylamine (0.580 mL, 4.2 mmol) in dichloromethane (11 mL) was added dropwise to a cooled (ice-bath), stirred solution of 2,4,6-trichloro-5-nitropyrimidine (Preparation 23a, 0.950 g, 4.2 mmol) in dichloromethane (25 mL). The mixture was warmed to ambient temperature and stirred overnight. After this period the mixture was concentrated and the residue was purified by flash chromatography (3:1 hexanes/ethyl acetate) to give the title compound (0.780 g, 67%) as a yellow solid. LRMS (m/z): 279 (M+1)+. 1H NMR delta (300 MHz, CDCl3): 3.62 (m, 4H), 3.77 (m, 4H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4359-87-9, its application will become more common.

Reference:
Patent; Almirall, S.A.; EP2527344; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 211244-81-4, Adding some certain compound to certain chemical reactions, such as: 211244-81-4, name is 2-(Methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one,molecular formula is C8H7N3OS, 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 211244-81-4.

7-chloro-2-(methylthio)pyrido[2,3-d]pyrimidine A suspension of 2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one (297 mg, 1.54 mmol) in POCI3 (6 mL) was stirred under argon at 80C for 16 hours. The solution was cooled, and the resulting precipitate was filtered and washed with EtOAc to afford the title compound (43 mg, 13%). The filtrate was diluted with EtOAc, washed with NaHC03 and dried with Na2S04. After removal of the solvent, a second crop was obtained (154 mg, 48%). [00317] H NMR (500 MHz, DMSO-d6): delta 9.52 (s, 1 H), 8.61 (d, J = 8.4 Hz, 1 H), 7.74 (d, J = 8.4 Hz, 1 H), 2.63 (s, 3H). LCMS (ESI) Rt =1 .98 minutes MS m/z 212 [M+H]+

According to the analysis of related databases, 211244-81-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; HOELDER, Swen; BLAGG, Julian; CHEUNG, Jack; ATRASH, Butrus; SHELDRAKE, Peter; WO2014/37751; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 22536-61-4, 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. 22536-61-4, name is 2-Chloro-5-methylpyrimidine. A new synthetic method of this compound is introduced below.

To a 500 mL RBF was added 2-chloro-5-methylpyrimidine (12 g, 93 mmol), potassium (E)- trifluoro(prop-1-en-1-yl)borate (17.27 g, 117 mmol), and potassium phosphate (59.4 g, 280 mmol). The flask was purged with N2(5x) and then 1,4-dioxane (200 mL) and water (20 mL) were added. The resulting yellow suspension was sparged with Ar for 15 min and then 1,1-bis[(di-t-butyl-p-methylaminophenyl]palladium(II) chloride (Amphos, commercially available from Strem, 2.64 g, 3.73 mmol) was added, a reflux condenser was attached, and the reaction was warmed to 90 C in an oil bath and stirred under N2for 16.5 h. The reaction was then cooled to RT. The reaction was diluted with water (250 mL) and extracted with EtOAc (2 x 250 mL). The organic layers were combined, dried (MgSO4), and concentrated. The residue was purified by flash chromatography on silica gel eluting with 0-20% EtOAc/hexanes) to afford (E)-5-methyl-2-(prop-1-en-1- yl)pyrimidine 466.01 (12.96 g, 97 mmol, 100% yield) as a yellow/orange oily solid.1H NMR (300 MHz, CDCl3) delta 8.49 (s, 2H), 7.01-7.20 (m, 1H), 6.57 (dd, J= 15.6, 1.7 Hz, 1H), 2.29 (s, 3H), 1.97 (dd, J= 6.8, 1.6 Hz, 3H). LCMS (ESI pos.) m/z: 135.2 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,22536-61-4, 2-Chloro-5-methylpyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; AMGEN INC.; CHEN, Ning; CHEN, Xiaoqi; CHEN, Yinhong; CHENG, Alan C.; CONNORS, Richard V.; DEIGNAN, Jeffrey; DRANSFIELD, Paul John; DU, Xiaohui; FU, Zice; HARVEY, James S.; HEATH, Julie Anne; HEUMANN, Lars V.; HORNE, Daniel B.; HOUZE, Jonathan; KALLER, Matthew R.; KAYSER, Frank; KHAKOO, Aarif Yusuf; KOPECKY, David J.; LAI, Su-Jen; MA, Zhihua; MEDINA, Julio C.; MIHALIC, Jeffrey T.; NISHIMURA, Nobuko; OLSON, Steven H.; PATTAROPONG, Vatee; SWAMINATH, Gayathri; WANG, Xiaodong; WANSKA, Malgorzata; YANG, Kevin; YEH, Wen-Chen; (700 pag.)WO2018/97945; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 5604-46-6 ,Some common heterocyclic compound, 5604-46-6, molecular formula is C5H3Cl2N3O, 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. Procedures for preparation of compound 11; NH2 H NH2 N”‘N 0 H p NN H ci cl (furoic hydrazide) ci H ou compound V CH3CN compound))) Na2CO3 40 Deg. C H0- NH NH2 80 Deg. C Zu NH2 Nu2 Nf H (at) N”S compound 11 Compound V (1. 0g, 1. Oeq.), 2-furoic hydrazide (0.7g, 1. 1 eq.) and sodium carbonate (0.55g, 1. Oeq. ) were added acetonitrile (20mL) and was heated to 40C. After stirring at 40C for 30 hours, the reaction was subsequently heated to 60C. A solution of 2- hydroxyethyl hydrazine (0.7mL, 2eq. ) in water (5mL) was added. The reaction mixture was then heated to 80C and stirred for 2.5 hours. Once the reaction was completed, the reaction mixture was cooled down to 25C, and 0.1 N HCI (10mL) was added. The reaction mixture was stirred at 25C for 2 hours. The reaction mixture was then concentrated to about 1 OmL under reduced pressure. Water (30mL) was added and the reaction mixture was concentrated to about 1 OmL under reduced pressure. The reaction mixture was stirred at 25C for overnight. The solid was filtered and washed with 2mL water, then with 2mL acetonitrile. The product (compound 1) was dried under vacuum at 25C to yield 1. 1 g (70%) of the desired product. LC/MS: m/z=304 (M+1) 1H NMR (DMSO-d6) : 610. 65 (d, 1H) ; 9.52 (d, 1H) ; 7.98-7. 88 (m, 1H) ; 7.42-7. 29 (m, 1H) ; 6.73-6. 70 (m, 1H) ; 6.35 (s, 2H); 4.9 (s, 1H) ; 4.1 (m, 2H); 3.62 (m, 2H)

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. 5604-46-6, 2-Amino-4,6-dichloropyrimidine-5-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SCHERING CORPORATION; WO2005/54245; (2005); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 89581-38-4, 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 89581-38-4 as follows.

To the reaction flask was added 1 mmol of compound F18,2 mmol Cs2CO3,1 ml of DMF and 2 mmol of 5-bromo-2-pyrimidinecarboxylic acid methyl ester. The reaction mixture was heated to 80 C for 2 h under nitrogen. After the reaction was complete, water was added. The organic phase was extracted with ethyl acetate, dried over anhydrous sodium sulfate, The filtrate was concentrated under reduced pressure and then purified using a silica gel column (petroleum ether: ethyl acetate = 1: 1 as eluent) to give the title product as a pale yellow oily liquid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,89581-38-4, its application will become more common.

Reference:
Patent; Guangdong Zhongsheng Pharmaceutical Co., Ltd.; Chen, Lijuan; Long, Chaofeng; Chen, Xiaoxin; Liu, Zhuowei; Ye, Haoyu; Xie, Chengshi; (104 pag.)CN106045923; (2016); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia