Pyrimidines

Electric Literature of 68797-61-5, 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.68797-61-5, name is 5-Bromo-4,6-dichloropyrimidine, molecular formula is C4HBrCl2N2, molecular weight is 227.87, as common compound, the synthetic route is as follows.

Step 1: Synthesis of 4,5,6-triphenylpyrimidine (abbreviation: Htppm))First, into a recovery flask equipped with a reflux pipe were put 4.25 g of 5-bromo-4,6-dichloropyrimidine, 6.84 g of phenylboronic acid, 5.95 g of sodium carbonate, 0.16 g of bis(triphenylphosphine)palladium(II)dichloride (abbreviation: Pd(PPh3)2Cl2), 20 mL of water, and 20 mL of acetonitrile, and the air in the flask was replaced with argon. This reaction container was heated by irradiation with microwaves (2.45 GHz, 100 W) for 60 minutes. Here, into the flask were further put 2.28 g of phenylboronic acid, 1.98 g of sodium carbonate, 0.053 g of Pd(PPh3)2Cl2, 5 mL of water, and 5 mL of acetonitrile, and the mixture was heated again by irradiation with microwaves (2.45 GHz, 100 W) for 60 minutes. After that, the precipitated solid was suction-filtered and washed with water. The obtained residue was purified by flash column chromatography using dichloromethane and ethyl acetate as a developing solvent in a ratio of 10:1, so that a pyrimidine derivative Htppm, which was the objective substance, was obtained (white powder, yield of 46 %). Note that the irradiation with microwaves was performed using a microwave synthesis system (Discover, manufactured by CEM Corporation). A synthesis scheme (1-1) of Step 1 is shown below.

Statistics shows that 68797-61-5 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-4,6-dichloropyrimidine.

Reference:
Patent; SEMICONDUCTOR ENERGY LABORATORY CO., LTD.; INOUE, Hideko; YAMAGUCHI, Tomoya; SHITAGAKI, Satoko; USHIKUBO, Takahiro; SEO, Satoshi; YAMADA, Yui; NOWATARI, Hiromi; WO2012/53627; (2012); 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. 1436686-17-7, name is Ethyl 5-bromopyrazolo[1,5-a]pyrimidine-3-carboxylate. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: Ethyl 5-bromopyrazolo[1,5-a]pyrimidine-3-carboxylate

General procedure: To a solution of 2.8 g (1 1 mmol) compound 1 -11 hydrogen chloride salt and 2.9 g (1 1 mmol) of compound 2 in 50 imL of EtOH was added 4.35 g (43.1 mmol) of EtaN. The mixture was stirred at 90 C for 2 h under nitrogen atmosphere and cooled to rt. It was concentrated under reduced pressure to afford a residue, which was purified by chromatography on silica gel column eluting with 20 % of ethyl acetate in petroleum ether to afford compound 1 -12. LC- MS: m/e = 416 [M+H]+.

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, 1436686-17-7, Ethyl 5-bromopyrazolo[1,5-a]pyrimidine-3-carboxylate.

Reference:
Patent; ANGEX PHARMACEUTICAL, INC.; WU, Wen-Lian; YANG, Zhiqiang; LEE, Francis; TAN, John Qiang; (112 pag.)WO2019/94143; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 767-15-7, 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. 767-15-7, name is 2-Amino-4,6-dimethylpyrimidine. A new synthetic method of this compound is introduced below.

General procedure: For the synthesis of 2, the solution of sulfurisocyanatidic chloride (7.2mmol) in 20mL toluene was added to the solution of 1 (6.0mmol) in 20mL toluene dropwise at room temperature. The reactant was heated to 140C and then the reaction proceeded for 18h under reflux. Subsequently, the mixture was cooled down to room temperature and remaining sulfurisocyanatidic chloride was removed under reduced pressure, together with the solvent. Without further purification, the resulting yellow oil 2 was dissolved in 10mL anhydrous acetonitrile and after that it was added slowly to 5mmol of 3, which was also dissolved in 10mL anhydrous acetonitrile beforehead in ice bath. After stirring for 24hat room temperature, acetonitrile was removed under reduced pressure and saturated sodium bicarbonate was added to product 4. Product 5 precipitated easily and it was further purified by recrystallization from petroleum ether/acetone in 1:1 ratio in high yields. 15% hydrochloric acid was added to aqueous solution of 5 under stirring and corresponding acidified product 4 precipitated out easily in high yields.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,767-15-7, 2-Amino-4,6-dimethylpyrimidine, and friends who are interested can also refer to it.

Reference:
Article; Wu, Ren-Jun; Ren, Tongtong; Gao, Jie-Yu; Wang, Li; Yu, Qilin; Yao, Zheng; Song, Guo-Qing; Ruan, Wei-Bin; Niu, Cong-Wei; Song, Fu-Hang; Zhang, Li-Xin; Li, Mingchun; Wang, Jian-Guo; European Journal of Medicinal Chemistry; vol. 162; (2019); p. 348 – 363;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 10397-13-4, 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. 10397-13-4, name is 4-(4,6-Dichloropyrimidin-2-yl)morpholine. A new synthetic method of this compound is introduced below.

4-(4,6-dichloropyrimidin-2-yl)morpholine (lOOmg 0.43mmol), pyridine-3-boronic acid (49mg, 0.4mmol), Cs2C03 ( 280mg, 0.86mmol) and Pd(PPh3)2Cl2 (20mg, 0.025mmol) were combined in dioxane (3ml) and water (1ml). The reaction mixture was then heated by microwave at 120C for 20min. Without purification (4-(3-cyclopropylureido)phenyl)boronic acid pinacol ester (130mg, 0.43mmol), Cs2C03 ( 280mg, 0.86mmol) and Pd(PPh3)2Cl2 (20mg, 0.025mmol) were added and the reaction mixture was then heated by microwave at 120C for a further 20min. The reaction mixture was partitioned between EtOAc and water. The organic layer was passed through a PTFE hydrophobic frit and the solvent removed in vacuo. Residual solid was triturated to give crude produect which was further purifed by prep LC/MS (low pH) to yield (9mg, 5%). 1H NMR (dg-DMSO) 9.45 (s, 1H), 8.72 (d, 1H), 8.65 (s, 1H), 8.61 (d, 1H), 8.22 (d, 2H), 7.87 (s, 1H), 7.58-7.55 (m, 3H), 6.51 (br s, 1H), 3.93-3.86 (m, 4H) 3.76-3.71 (m, 4H), 2.58-2.52 (m, 1H), 0.67-0.62 (m, 2H), 0.44-0.40 (m, 2H);LCMS (method B), (M+H+) 417, Rt = 2.24min.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,10397-13-4, 4-(4,6-Dichloropyrimidin-2-yl)morpholine, and friends who are interested can also refer to it.

Reference:
Patent; CELLZOME LIMITED; LYNCH, Rosemary; CANSFIELD, Andrew, David; NIBLOCK, Helen, Sarah; HARDY, Daniel, Paul; TAYLOR, Jessica; WO2011/107585; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 40805-79-6, 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 40805-79-6, name is 5-Pyrimidinecarbonitrile. This compound has unique chemical properties. The synthetic route is as follows.

In a 250 mL round-bottomed flask, pyrimidine-5-carbonitrile (1.5 g, 14.3 mmol), pyridine (0.339 g, 0.35 ml, 28.5 mmol), and 2-mercaptopropionic acid (1.51 g, 14.3 mmol) were combined to give a light yellow solution. The reaction mixture was heated to 100 C. and stirred for 2 h. Upon cooling, the thick yellow mixture was diluted with 100 mL ethanol and stirred for 30 min. The slurry was then filtered, and washed with diethyl ether (2*100 mL) to give 5-Methyl-2-(pyrimidin-2-yl)-thiazol-4-ol (2.33 g, 85%) as yellow solid which was used directly 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 40805-79-6, 5-Pyrimidinecarbonitrile.

Reference:
Patent; Alam, Muzaffar; Du Bois, Daisy Joe; Hawley, Ronald Charles; Kennedy-Smith, Joshua; Minatti, Ana Elena; Palmer, Wylie Solang; Silva, Tania; Wilhelm, Robert Stephen; US2011/71150; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 696-07-1, Adding some certain compound to certain chemical reactions, such as: 696-07-1, name is 5-Iodouracil,molecular formula is C4H3IN2O2, 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 696-07-1.

General procedure: To a solution of 5-iodopyrimidine (0.84 mmol) in anhydrous DMF (7 mL) were added the terminal alkyne (2.5 mmol), Pd(PPh3)4 (0.08 mmol), CuI (0.08 mmol) and Et3N [or (iPr)2EtN] (1.68 mmol). Method A: The reaction mixture was stirred at room temperature overnight. The extent of the reaction was monitored by TLC and the solvent was evaporated in vacuo and the residue purified by column chromatography (initial eluent CH2Cl2, then CH2Cl2/MeOH = 40:1) to afford 1-10a and 1-6b. Method B: The synthesis was carried out at 50 C for 30 min under microwave irradiation (300 W, 1 bar, Milestone start S microwave oven). Purification by column chromatography (initial eluent CH2Cl2, then CH2Cl2/MeOH = 40:1) afforded compounds 1-10a and 1-6b.

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. 696-07-1, 5-Iodouracil, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Kraljevi?, Tatjana Gazivoda; Bistrovi?, Andrea; Dedi?, Matea; Paveli?, Sandra Kraljevi?; Sedi?, Mirela; Rai?-Mali?, Silvana; Tetrahedron Letters; vol. 53; 38; (2012); p. 5144 – 5147;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 42839-09-8, 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 42839-09-8, name is 2-Pyrimidinemethanol. This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 9 A mixture of 7.2 g. of 2-pyrimidinemethanol and 25 ml. of thionyl chloride is heated for 4 hours on a steam bath, then concentrated under reduced pressure. The residue is dissolved in water and basified with 5% aqueous sodium bicarbonate solution. Extracting with ether, then drying and concentrating the extracts gives 2-(chloromethyl)pyrimidine.

According to the analysis of related databases, 42839-09-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SmithKline Corporation; US3966945; (1976); A;,
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.1820-81-1, name is 5-Chlorouracil, molecular formula is C4H3ClN2O2, molecular weight is 146.53, as common compound, the synthetic route is as follows.category: pyrimidines

General procedure: A mixture of 5-fluorouracil (50.5 mg, 0.39 mmol), pyridine (0.60 mL), and HMDS (1.2 mL) in a20-mL Schlenk tube was refluxed (oil bath temp., 140 C) for ca. 30 min to give a clear solution of 2a. All the volatiles were then removed under reduced pressure (ca. 1mmHg) to give a clear syrup, which was dissolved in MeCN (3.0 mL). To this were added 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose (1) (151.5 mg, 0.30 mmol) and6 (5.8 mg, 15 mumol), and the mixture was stirred under reflux (oil bath temp., 80 C) for6 h. The reaction mass was cooled to rt and EtOAc (2 mL) was added to it, followed by saturated NaHCO3 solution (2 mL). After the mixture was stirred at 0 C for 15min, EtOAc (30 mL) and saturated NaHCO3 solution (20 mL) were added to it. The organic phase was separated and the aqueous phase was back-extracted with EtOAc (3 x30 mL). The combined organic layer was dried over Na2SO4 and evaporated to afforda foamy white crude material, which was crystallized from EtOAc (10 mL) and hexane(20 mL) as a white solid (139.2 mg). The mother liquor was purified by column chromatography (Silica Gel 60, 8 g, EtOAc:hexane = 30:70 35:65) to afford the titlecompound 3a (15.6 mg). The combined yield was 90% (155 mg). 1H and 13C NMR spectra were consistent with the reported ones.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1820-81-1, 5-Chlorouracil, and friends who are interested can also refer to it.

Reference:
Article; Basu, Nabamita; Oyama, Kin-ichi; Tsukamoto, Masaki; Tetrahedron Letters; vol. 58; 20; (2017); p. 1921 – 1924;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 862730-04-9, Adding some certain compound to certain chemical reactions, such as: 862730-04-9, name is 3-Iodo-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine,molecular formula is C8H10IN5, 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 862730-04-9.

Synthesis of (3-(4-amino-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl)phenyl)methanol (BA26); A solution of (3-Hydroxymethylphenyl)boronic acid (24 mg, 0.13 mmol) in EtOH (3.3 ml) was added to a solution of 3-iodo-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine (20 mg, 0.07 mmol) in DME (12 ml). Pd(PPh3)4 (16 mg, 0.014 mmol) and saturated Na2CO3 (1.9 ml) were added and the reaction was heated to 80 C. under an argon atmosphere overnight. After cooling, the reaction was extracted with saturated NaCl and CH2Cl2. Organic phases were combined, concentrated in vacuo and purified by RP-HPLC (MeCN:H2O:0.1% TFA) to yield BA26 (8.4 mg, 42% yield). ESI-MS (M+H)+ m/z calcd 283.1, found 284.2.

According to the analysis of related databases, 862730-04-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Regents of the University of California; US2007/293516; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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 110100-00-0, name is 1-(2-Chloropyrimidin-5-yl)ethanone. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C6H5ClN2O

To a stirred solution of Intermediate 16 (1.14 g, 4.24 mmol) in dry DMF (10 mL), TEA (1.1 mL, 16.5 mmol) and 1-(2-chloropyrimidin-5-yl)ethan-1-one obtained in the previous step (0.6 g, 3.85 mmol) were added at rt. The resulting mixture was heated to 90 C for 12 h. It was cooled to rt and concentrated. Dichloromethane (50 mL) was added and was washed with a saturated NaCI solution (10 mL), dried over anhydrous Na2SO4 and concentrated. The crude product was purified by flash chromatography, affording the title compound (off white solid). 1H NMR (400 MHz, DMSO-d6): delta 8.83 (s, 2H), 6.90 (s, 1H), 6.84 (d, J = 7.6 Hz, 1H), 6.74 (dd, J = 8.0, 1.2 Hz, 1H), 5.99-5.98 (m, 2H), 3.84 (t, J = 4.8 Hz, 4H), 3.40-3.36 (m, 1H), 2.49-2.47 (m, 5H), 2.38-2.35 (m, 2H), 1.27 (d, J = 6.8 Hz, 3H). LCMS: (Method A) 355.0 (M+H), Rt. 2.61 min, 99.78% (Max). HPLC: (Method A) Rt. 2.55 min, 99.51 % (Max).

With the rapid development of chemical substances, we look forward to future research findings about 110100-00-0.

Reference:
Patent; ASCENEURON SA; QUATTROPANI, Anna; KULKARNI, Santosh S.; GIRI, Awadut Gajendra; (243 pag.)WO2016/30443; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia