Pyrimidines

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. 4595-60-2, name is 2-Bromopyrimidine, molecular formula is C4H3BrN2, 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. category: pyrimidines

4-Bromo-2-fluorophenyl boronic acid (2AB) (3.Og, 13.71 mmol, 1 equiv), 2- bromopyrimidine (1AB) (6.54 g, 41.13 mmol, 3 equiv), and 2M sodium carbonate (34 ml_) were added in a pressure vessel (350 ml_) and a (1 v : 1 v) mixture of toluene and ethanol (45 ml_ : 45 ml_) was added. The mixture was then bubbled with nitrogen gas for about 10 minutes. Tetrakistriphenylphosphine palladium (0) (793mg, 0.686 mmol, 0.05 equiv) was added to the mixture. The reaction vessel was tightly capped, placed in an oil bath at 9OC and stirred overnight. The reaction mixture was. cooled down to room temperature and the content was filtered into a flask and the solvent mixture was evaporated off on the rotovap. The residue was then taken up in one to one mixture of toluene and ethyl acetate and washed with (3v : 1v) mixture of brine and Dl water twice. The organic layer was separated and combined and dried over magnesium sulfate. The crude product was then filtered into a flask and the solvent was removed on rotovap. The residue was taken up in as little dichloromethane as possible and purified by column chromatography using Analogix purification system with the following conditions: Solvent A: Hexanes; Solvent B: Ethylacetate. Flow Rate: 65 mL/min. Gradient: 0% Solvent B to 50% Solvent B in 60 minutes. Yield= 2.79 g (80.4%)

With the rapid development of chemical substances, we look forward to future research findings about 4595-60-2.

Reference:
Patent; SCHERING CORPORATION; WO2008/153858; (2008); 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. 211244-81-4, name is 2-(Methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one, molecular formula is C8H7N3OS, 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. Recommanded Product: 2-(Methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one

Example 278 8-Cyclopropyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one The title compound was prepared from 2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one (3 g, 15.5 mmol) and bromomethyl cyclopropane (1.6 mL, 16 mmol) by using the procedure described in Example 272.

With the rapid development of chemical substances, we look forward to future research findings about 211244-81-4.

Reference:
Patent; Booth, Richard John; Chatterjee, Arindam; Malone, Thomas Charles; US2004/224958; (2004); A1;,
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Pyrimidine – Wikipedia

Electric Literature of 3764-01-0, 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 3764-01-0, name is 2,4,6-Trichloropyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

A suspension of 2,4,6-trichloropyrimidine (1000 mg, 5.29mmol), phenyl boronic acid (665 mg, 5.29 mmol), PdC12(dppf) dichloromethane complex (204 mg, 0.26 mmcl) and K2C03 2 M solution (5.3 ml, 10.58 mmol) in 1,4-dioxane (26.4 ml) was stirred in a CEM microwave apparatus at 60 C for 1 hour.Resulting crude was portioned between dichloromethane (150 ml), NaHCO3 saturated solution (100 ml), the organic layer dried over Na2SO4 and concentrated to dryness at low pressure. Final normal phase purification (cyclohexane/DCM from 100/0 to 85/15) afforded pure title compound (857 mg,yield 72 %) . Rt = 1.38 mm (analysis method 2); MS (ESI)m/z: 225.1 [M-H], [M-H] calculated: 225.0. ?H NMR (400MHz, CDC13) 6 8.13 – 8.03 (m, 2H), 7.68 (s, 1H), 7.62 – 7.48(m, 3H)

According to the analysis of related databases, 3764-01-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; FONDAZIONE ISTITUTO ITALIANO DI TECNOLOGIA; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; DE VIVO, Marco; GANESAN, Anand; ORTEGA MARTINEZ, Jose Antonio; JAHID, Sohail; (84 pag.)WO2018/203256; (2018); A1;,
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Pyrimidine – Wikipedia

Application of 7400-06-8, 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. 7400-06-8, name is 6-Amino-5-(2,2-diethoxyethyl)pyrimidin-4-ol, molecular formula is C10H17N3O3, 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.

7H-Pyrrolo[2,3-d]pyrimidin-4-ol (7).; Formamidine acetate (5, 1.04 Kg,10 mol, 1.25 equiv) was added to 7.52 L of (21percent wt) sodium ethoxide (EtONa) in ethanol (EtOH, 62.5 equiv) and the resulting solution was stirred for 60 minutes. 2-cyano-4,4-diethoxy-butyric acid ethyl ester (4, 1.8 Kg, 8.0 mol) was then added and the resulting reaction mixture was refluxed for seven hours. The stirring was turned off after the solution was cooled and the solids were allowed to settle. The supernatant ethanol solution was removed, leaving the solids in the bottom of the reaction flask. The ethanol was evaporated and the residue was added back to the solids remaining in the reaction flask with water and ice at a ratio of 600 mL/mol. A solution of 6 N aqueous HCl was added to the resulting solution at a ratio of 500 mL/mol at 15° C. The resulting solution was then heated at 45° C. for 45 minutes. The solution was again cooled to 15° C. and the pH was adjusted to 8.0 with the addition of aqueous ammonium hydroxide. The precipitated solids were collected by filtration, washed with water (2.x.225 mL/mol) and pulled dry. The solids were further washed with 1:1 ethyl acetate/heptane (500 mL/mol), then heptane (2.x.250 mL/mol) and dried in vacuum to afford 7H-pyrrolo[2,3-d]pyrimidin-4-ol (7, 738.6g, 1081 g theoretical, 68.3percent) as yellow to brown to yellow crystalline material. For 7: 1H NMR (DMSO-d6, 300 MHz) delta ppm 11.88 (bs, 1H), 11.80 (bs, 1H), 7.81 (s,1H), 7.02 (dd,1H, J=3.2, 2.3 Hz), 6.42 (dd, 1H, J=3.5, 2.3 Hz); C6H5N3O (MW, 135.12), LCMS (EI) m/e 136 (M++H) and (M++Na) m/e 158.

According to the analysis of related databases, 7400-06-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Zhou, Jiacheng; Liu, Pingli; Lin, Qiyan; Metcalf, Brian W.; Meloni, David; Pan, Yongchun; Xia, Michael; Li, Mei; Yue, Tai-Yuen; Rodgers, James D.; Wang, Haisheng; US2010/190981; (2010); A1;,
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Pyrimidine – Wikipedia

Application of 663194-10-3, Adding some certain compound to certain chemical reactions, such as: 663194-10-3, name is 4-(4-Bromopyrimidin-2-yl)morpholine,molecular formula is C8H10BrN3O, 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 663194-10-3.

In Nu,Nu-dimethylformamide (DMF) (537 mu) was dissolved 4- (difluoromethyl)-N-(4-fluoro-5-(tributylstannyl)-2-((3S,5R)-3,4,5-trimethylpiperazin- l-yl)phenyl)-6-(2-(trimethylsilyl)ethoxy Nicotinamide (107 mg, 0.134 mmol). To the solution was added 4-(4-bromopyrimidin-2-yl)morpholine (36.0 mg, 0.148 mmol), lithium chloride (17.06 mg, 0.402 mmol) and bis(triphenylphosphine)palladium(II) dichloride (5.18 mg, 7.38 muetaiotaomicron) at room temperature and then it was microwaved at the temperature of 120 °C for 3 hours. To the reaction mixture was added water and then extracted with dichloromethane. The organic layer was separated, concentrated and purified by column chromatography on silica gel (0-100percent, 89percent CH2C12, 10percent MeOH, 1percent NH4Ac/CH2Cl2) to afford the title compound. LCMS [M+l]+ = 672.43.

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. 663194-10-3, 4-(4-Bromopyrimidin-2-yl)morpholine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ONTARIO INSTITUTE FOR CANCER RESEARCH (OICR); AL-AWAR, Rima; ZEPEDA-VELAZQUEZ, Carlos Armando; PODA, Gennady; ISAAC, Methvin; UEHLING, David; WILSON, Brian; JOSEPH, Babu; LIU, Yong; SUBRAMANIAN, Pandiaraju; MAMAI, Ahmed; PRAKESCH, Michael; STILLE, Julia Kathleen; (1053 pag.)WO2017/147700; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 3764-01-0, Adding some certain compound to certain chemical reactions, such as: 3764-01-0, name is 2,4,6-Trichloropyrimidine,molecular formula is C4HCl3N2, 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 3764-01-0.

A solution of methylamine (57 ml of a 2M solution in THF) was added dropwise to a stirred solution of trichlo50 ropyrimidine (124a; 10.00 g) in anhydrous THF (80 ml) at-20 C, under an atmosphere of nitrogen and the reaction was maintained at this temperature for 0.5 h. The volatiles were removed under reduced pressure and the residue partitionedbetween methylene chloride and 10% aq. NaOH. Theorganic phase was separated, washed with water, dried(MgSO4), and concentrated under reduced pressure. The residue was purified by silica gel colunm chromatography using EtOAc; hexanes (1:20) as eluent to give the desiredproduct (312i; 4.05 g) as a white solid. The relatively morepolar isomer (312j) was set aside at this time.

According to the analysis of related databases, 3764-01-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Merck Sharp & Dohme Corp.; Southern Research Institute; Arasappan, Ashok; Njoroge, F. George; Kwong, Cecil D.; Ananthan, Subramaniam; Bennett, Frank; Velazquez, Francisco; Girijavallabhan, Vinay M.; Huang, Yuhua; Kezar, III, Hollis S.; Maddry, Joseph A.; Reynolds, Robert C.; Roychowdhury, Abhijit; Fowler, Anita T.; Secrist, III, John A.; Kozlowski, Joseph A.; Shankar, Bandarpalle B.; Tong, Ling; Kim, Seong Heon; MacCoss, Malcolm; Venkatraman, Srikanth; Verma, Vishal; (798 pag.)US9433621; (2016); B2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 941685-26-3, 4-Chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]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, Safety of 4-Chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine, blongs to pyrimidines compound. Safety of 4-Chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine

A 100 mL round bottom flask was charged with 4-chloro-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine (1.00 g, 3.52 mmol), 1-butanol (25.0 mL), [1-(triisopropylsilyl)-1H-pyrrol-3-yl]boronic acid (1.41 g, 5.28 mmol), water (25.0 mL) and potassium carbonate (1.27 g, 8.8 mmol). This solution was degased 4 times, filling with nitrogen each time. Tetrakis(triphenylphosphine)-palladium(0) (0.41 g, 0.35 mmol) was added and the mixture was degased 4 times, filling with nitrogen each time. The reaction was stirred overnight at 100 C. and cooled to room temperature. The mixture was filtered through a bed of celite and the celite was rinsed with ethyl acetate (42 mL). The filtrate was combined and the organic layer was separated. The aqueous layer was extracted with ethyl acetate. The organic extracts were combined and concentrated under vacuum with a bath temperature of 30-70 C. to give the title compound 4-(1H-pyrrol-3-yl)-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine. Yield: 83%; LC-MS: 315.2 (M+H)+.

The synthetic route of 941685-26-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Huang, Taisheng; Xue, Chu-Biao; Wang, Anlai; Kong, Ling Quan; Ye, Hai Fen; Yao, Wenqing; Rodgers, James D.; Shepard, Stacey; Wang, Haisheng; Shao, Lixin; Li, Hui-Yin; Li, Qun; US2011/224190; (2011); A1;,
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.5305-59-9, name is 6-Chloropyrimidin-4-amine, molecular formula is C4H4ClN3, molecular weight is 129.55, as common compound, the synthetic route is as follows.Product Details of 5305-59-9

Reference Example 9 6-Aminopyrimidine-4-carboxylic acid propyl ester A mixture of 6-chloro-4-aminopyrimidine (2.00 g, 15.4 mmol), palladium acetate (361 mg, 1.61 mmol), 1,3-bis(diphenylphosphino)propane (631 mg, 1.52 mmol), and potassium carbonate (2.55 g, 18.5 mmol) in n-propanol (45 mL) and DMF (15 mL) was stirred at 90C under carbon monoxide atmosphere. The mixture was allowed to stand and cool to room temperature, and then filtered through Celite. Aqueous sodium bicarbonate solution was added to the filtrate, which was extracted with ethyl acetate. The organic phase was washed with saturated brine and dried over anhydrous magnesium sulfate, and then the solvent was evaporated off in vacuo. The residue was purified by column chromatography on silica gel (chloroform/methanol = 100/1 to 50/1) to give the title compound (1.86 g, 10.3 mmol, yield 67%). 1H-NMR (delta ppm, CDCl3): 8.71 (d, J = 1.2 Hz, 1H), 7.17 (d, J = 1.2 Hz, 1H), 5.16 (br, 2H), 4.35 (t, J = 6.9 Hz, 2H), 1.83 (tq, J = 7.4, 6.9 Hz, 2H), 1.02 (t, J = 7.4 Hz, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,5305-59-9, 6-Chloropyrimidin-4-amine, and friends who are interested can also refer to it.

Reference:
Patent; Kyowa Hakko Kirin Co., Ltd.; EP2070927; (2009); 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. 146533-41-7, name is 5-(4-Bromophenyl)-4,6-dichloropyrimidine, molecular formula is C10H5BrCl2N2, 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. Product Details of 146533-41-7

To a solution of 5-(4-bromophenyl)-4,6-dichloro-pyrimidine (100 g) in dimethyl sulfoxide (700 ml), potassium(N-propylsulfamoyl)amide (145 g) was added at 25-30C under nitrogen atmosphere and stirred for 10 hrs. After reaction completion, pH of the reaction mass was adjusted to 2-3 using aqueous hydrochloric acid at 25-30C and stirred for 75 mins. The solid obtained was filtered, washed with water and suck dried under vacuum. Methanol (3500 ml) was added to the above compound and heated to reflux temperature then stirred for an hour at reflux. The reaction mass was distilled upto 450-550 mL remained in the flask. The reaction mass was cooled to 25-30C, stirred for 75 mins then further cooled to 0- 5C and stirred for 75 mins. The obtained solid was filtered, washed with methanol and dried under vacuum at 50-55C for 4 hrs to get the title compound. Yield: 110 g; Purity by HPLC: 99.10%

With the rapid development of chemical substances, we look forward to future research findings about 146533-41-7.

Reference:
Patent; LAURUS LABS PRIVATE LIMITED; JAMJANAM, Srivardhana Rao; MOTURU, Venkata Ramakrishna Murthy; INDUKURI, Venkata Sunil Kumar; KALIDINDI, Srihari Raju; CHAVA, Satyanarayana; (37 pag.)WO2017/93903; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 24415-66-5, 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 24415-66-5 as follows.

Adding 85 mg (about 0.5 mmol) to a 10 mL microwave reaction tube.7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine and 228 mg (about 1.5 mmol) of 6-chloroindole, 14 mg (about 10 mol%) of the catalyst bistrifluoromethylsulfonimide and 1 mL of the solvent HFIP, and then the microwave reaction tube was sealed.Then, the reactant in the microwave reaction tube was stirred at 100 C for 6 hours, and the solvent was distilled off under reduced pressure.And purified by column chromatography using DCM / MeOH as eluent to give about 108 mg of pure product e9 as a yellow solid with a yield of 76%;

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,24415-66-5, its application will become more common.

Reference:
Patent; Zhengzhou University; Liu Hongmin; Yu Bin; Yuan Shuo; Wang Shuai; Li Zhonghua; (21 pag.)CN109180684; (2019); A;,
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Pyrimidine – Wikipedia