Category: pyrimidines

Reference of 63200-54-4 ,Some common heterocyclic compound, 63200-54-4, molecular formula is C6H3Cl2N3, 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 solution of 2,4-dichloro-5H-pyrrolo[3,2-d]pyrimidine (1.00 g, 5.26 mmol) in DCM (5 mL) was added phenylboronic acid (710 mg, 5.79 mmol), cupric acetate (1.82 g, 10.52 mmol), Et3N (5.32 g, 53.62 mmol). Then the reaction mixture was stirred in oxygen atmosphere at rt overnight. Water (50 mL) was added to quench the reaction, and the mixture was partitioned. The aqueous layer was extracted with EtOAc (50 mL x 2). The combined organic layers were washed with saturated brine (80 mL), dried over anhydrous Na2504 and filtered. The filtrate was concentrated in vacuo and the residue was purified by silica gel chromatograph (PE/EtOAc (v/v) = 10/1) to give the title compound as a yellow solid (1.03 g, 74 %).MS (ESI, pos. ion) m/z: 265.20 [Mib.

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. 63200-54-4, 2,4-Dichloro-5H-pyrrolo[3,2-d]pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Yingjun; REN, Qingyun; TANG, Changhua; LIN, Xiaohong; YIN, Junjun; YI, Kai; (270 pag.)WO2017/97234; (2017); 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 10070-92-5, name is Pyrimidine-5-carbaldehyde. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 10070-92-5

General procedure: The equimolar amount 6-(1H-indol-3-yl)-4,5?-bipyrimidine-2-amine and substituted aldehydes were mixed in a round bottom flask containing 50 mL of ethanol, some droplets of glacial acetic acid were added to the mixture, and it was set on refluxing for 18 h. Solid product was observed on the completion of reaction that was filtered and dried under vacuum and recrystallized using proper solvent [50].

With the rapid development of chemical substances, we look forward to future research findings about 10070-92-5.

Reference:
Article; Arshad, Mohammad; Journal of the Iranian Chemical Society; vol. 17; 6; (2020); p. 1305 – 1315;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 16019-33-3, 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.16019-33-3, name is 2-(4,6-Dichloropyrimidin-5-yl)acetaldehyde, molecular formula is C6H4Cl2N2O, molecular weight is 191.02, as common compound, the synthetic route is as follows.

To the stirred solution of (R)-3-amino-pyrrolidine-1 -carboxylic acid tert-butyl ester (CAS 147081-49-0; 4.68 g, 25.1 mmol, 1.0 eq) and EtOH (50 mL) was added N,N- diisopropylamine (4.30 mL, 25.1 mmol, 1.0 eq) and 4,6-dichloro-pyrimidin-5-yl)-acetaldehyde (CAS 16019-33-3; 4.80 g, 25.1 mmol,). The reaction mixture was stirred for 8h at reflux temperature and then concentrated. The residue was dissolved in THF (37.5 mL) and HCI 4M (12.5 mL) was added at 0 C and stirred for an additional hour at 0 C. The reaction mixture was partitioned between Na2C03 1 M and EtOAc. The combined organic layers were washed with brine, dried (Na2S0 ), filtered and concentrated. The residue was purified by silica gel column chromatography (EtOAc – nheptane 1 :1 ) to afford 6.70 g of the title compound as a yellow oil: HPLC-MS: M+H = 323.4 (Rt = 1.27) (Method X): TLC; R, = 0.19 (EtOAc – n heptane 1 :2).

Statistics shows that 16019-33-3 is playing an increasingly important role. we look forward to future research findings about 2-(4,6-Dichloropyrimidin-5-yl)acetaldehyde.

Reference:
Patent; NOVARTIS AG; IRM LLC; CHEN, Bei; FAIRHURST, Robin, Alec; FLOERSHEIMER, Andreas; FURET, Pascal; GUAGNANO, Vito; JIANG, Songchun; LU, Wenshuo; MARSILJE, Thomas, H.; MCCARTHY, Clive; MICHELLYS, Pierre-Yves; STAUFFER, Frederic; STUTZ, Stefan; VAUPEL, Andrea; WO2011/29915; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 428854-24-4, 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 428854-24-4, name is 2-(1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl)pyrimidine-4,5,6-triamine. This compound has unique chemical properties. The synthetic route is as follows.

Example 51 4-Amino-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-5,8-dihydropteridine-6,7-dione 300 mg (0.856 mmol) of the compound from example 1A were dissolved in 3 ml of ethanol, and 116 mul (0.856 mmol) of diethyl oxalate and 79 mg (1.156 mmol) of sodium methoxide were added. The mixture was heated to reflux for 10 h. The reaction mixture was stirred with 10 ml of ethanol. The precipitate was filtered off and stirred with 10 ml of water and then with 10 ml of acetonitrile. The precipitate was filtered off and dried under high vacuum. 112 mg of the title compound were obtained (30% of theory). LC-MS (method 2): Rt=0.80 min; MS (EIpos): m/z=405 (M+H)+. 1H NMR (400 MHz, DMSO-d6): delta [ppm]=5.82 (s, 2H), 7.12-7.25 (m, 4H), 7.33-7.40 (m, 2H), 8.64 (dd, 1H), 9.14 (dd, 1H), 12.44 (s, 1H).

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 428854-24-4, 2-(1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl)pyrimidine-4,5,6-triamine.

Reference:
Patent; BAYER INTELLECTUAL PROPERTY GMBH; Follmann, Markus; Stasch, Johannes-Peter; Redlich, Gorden; Ackerstaff, Jens; Griebenow, Nils; Knorr, Andreas; Wunder, Frank; Li, Volkhart Min-Jian; Baerfacker, Lars; Weigand, Stefan; US2014/148433; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 876343-10-1 , The common heterocyclic compound, 876343-10-1, name is 4-Chloro-6-iodo-7H-pyrrolo[2,3-d]pyrimidine, molecular formula is C6H3ClIN3, 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.

te^-ButyI4-(4-chloro-7Jy-pyrrolo[2,3-«qpyrimidm-6-yl)-3,6-dihydropyridine-l(2fl)-carboxylate (compound of Formula VIII-Boc).; IXMKCn[228] To a suspension of 4-chloro-6-iodo-7H-pyrrolo[2,3-d]pyrimidine (5.0g,O.OlSmol) in 1,4-dioxane (120mL) and water (30mL) were added 4-(4,4,5,5-tetramethyl-[l,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-l-carboxylic acid tert-butyl ester (5.97g,0.0193mol), potassium carbonate (4.9g, 0.036mol) and PdCl2(dppf)-CH2Cl2 (0.73g,0.89mmol). The flask was evacuated and refilled with N2 (3x). The mixture was heated at100C overnight. LC-MS showed the reaction was complete. The mixture was diluted withethyl acetate (200mL), then washed with brine (2x50mL), and dried over anhydrous sodiumsulfate. The filtrate was concentrated under reduced pressure to wlOOmL, the resulting whiteprecipitate was collected by filtration to give the first batch of the title compound. The filtratewas concentrated and the residue was purified by chromatography on silica gel, eluting withHex:EtOAc = 70:30 -> 50:50 to give a white solid (containing pinacol), which was furthercrystallized with EtOAc/hexanes to give the second batch of the title compound as a whitesolid. LC-MS (ES, Pos.): 335/337 (3/1) [MH+]. ‘H NMR (CDC13,400 MHz): 5 = 1.51 (s,9H), 2.61 (m, 2H), 3.70 (m, 2H), 4.20 (m, 2H), 6.27 (s, 1H), 6.55 (s, 1H), 8.61 (s, 1H), 10.3(brs, 1H).

The synthetic route of 876343-10-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; OSI PHARMACEUTICALS, INC.; WO2006/17443; (2006); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 22536-65-8, 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 22536-65-8, name is 2-Chloro-5-methoxypyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

Intermediate 58C (45 mg, 0.124 mmol) was dissolved in Dioxane (621 mu) and 2- chloro-5-methoxypyrimidine (26.9 mg, 0.186 mmol), dicyclohexyl(2′,4′,6′-triisopropyl- 3,6-dimethoxy-[l, l’-biphenyl]-2-yl)phosphine (6.66 mg, 0.012 mmol), sodium tert- butoxide (17.89 mg, 0.186 mmol), and palladium(II) acetate (2.79 mg, 0.012 mmol) were added. Reaction was degassed with nitrogen bubbling/sonication for 5 minutes, then it was sealed at heated to 85 C for 14 hours. The reaction was diluted with water, acidified with 1 N HC1, and extracted with EtOAc. The combined organics were dried with sodium sulfate, filtered and concentrated. The crude residue was dissolved in DMF, filtered, and purified via preparative HPLC to give Racemic Example 63 (2.5 mg, 0.006 mmol, 4.6%). LC-MS Anal. Calc’d for C24H34N4O4 442.26, found [M+H] 443.3. Tr = 1.869 min (Method B). 1H MR (500 MHz, DMSO-d6) delta: 8.62 (s, IH), 8.34 (s, 2H), 8.12 (d, J=2.7 Hz, IH), 7.14 (d, J=8.7 Hz, IH), 6.35 (dd, J=8.5, 2.7 Hz, IH), 4.72 (q, J=6.5 Hz, IH), 3.83 (s, 3H), 1.76-1.91 (m, 2H), 1.67 (d, J=10.9 Hz, 2H), 1.51-1.54 (m, IH), 1.49 (d, J=6.6 Hz, 3H), 1.15 (t, J=7.2 Hz, 9H), 0.81 (br. s., 6H)

According to the analysis of related databases, 22536-65-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BALOG, James Aaron; CHERNEY, Emily Charlotte; MARKWALDER, Jay A.; SHAN, Weifang; WILLIAMS, David K.; (203 pag.)WO2016/210414; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 514854-13-8, 6-Ethyl-5-iodopyrimidine-2,4-diamine, 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, 514854-13-8, blongs to pyrimidines compound. Recommanded Product: 6-Ethyl-5-iodopyrimidine-2,4-diamine

General procedure: The alkyne (1.2 eq), iododiaminoethyl pyrimidine (1.0 eq) was dissolved in anhydrous DMF (0.15M) and sonicated under argon. Pd(PPh3)2Cl2 (0.1 eq), CuI (0.21 eq), Et3N (24 eq) were added and again sonicated under argon for 15 minutes. The reaction mixture was heated at 60 C for 12h under argon. The reaction mixture was then concentrated in vacuo before preabsorbing onto a mixture of amine and 25% cysteine preabsorbed silica gel (1:1 /wt) and filterted through a plug of silica gel with 5% MeOH/ CH2Cl2. The collected reaction mixture was concentrated in vacuo, and further purified by preparative HPLC to furnish the final product

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,514854-13-8, its application will become more common.

Reference:
Article; Lombardo; Dayanandan; Keshipeddy; Zhou; Si; Reeve; Alverson; Barney; Walker; Hoody; Priestley; Obach; Wright; Drug Metabolism and Disposition; vol. 47; 9; (2019); p. 995 – 1003;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 2565-47-1, 1-Methylpyrimidine-2,4,6(1H,3H,5H)-trione, 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, Computed Properties of C5H6N2O3, blongs to pyrimidines compound. Computed Properties of C5H6N2O3

(B) The 1-methylpyrimidine-2,4,6-trione prepared above is uniformly mixed with phosphorus oxychloride, and then controlled to react at 0 C for 0.8 h, followed by controlling the reaction at 50 C. After 1.5 h, finally purified and dried to obtain 3-methyl-6-chlorouracil

The synthetic route of 2565-47-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Anyang Normal University; Wang Xin; Sun Kai; Lv Yunhe; (12 pag.)CN109503551; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 57564-94-0, 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 57564-94-0 as follows.

To a mixture of sodium hydride (60% dispersion in mineral oil; 276 mg; 6.89 mmol) in DMF (10 mL) at 0 C was added drop-wise a solution of 4-chloro-2-methylsulfanyl-7H-pyrrolo[2,3-d]pyrimidine [prepared as detailed in Ref. 45] (1.145 g; 5.74 mmol) in anhydrous DMF (20 mL). When the addition was complete, 2-(trimethylsilyl)ethoxymethyl chloride (1.32 ml; 7.46 mmol) was added drop-wise and the reaction mixture was stirred at 0 C for 1.5 h then allowed to warm to ambient temperature. The reaction mixture was partitioned between water (100 mL) and ethyl acetate (100 mL). The organic phase was separated, dried over Na2SO4 and then filtered and the filtrate solvents evaporated in vacuo. The crude product was purified by flash chromatography on silica gel (70 g) eluting with a solvent gradient of 0-5% ethyl acetate in hexane to afford the title compound 42 (1.73 g, 91%) as a colourless oil: LC-MS (method A) tR = 2.88 min; m/z = 332, 330 [M+H]+; 1H NMR (400 MHz, DMSO-d6): delta -0.10 (s, 9H), 0.84 (t, 2H, J = 8.1 Hz), 2.53 (s, 3H), 3.52 (t, 2H, J = 8.1 Hz), 5.58 (s, 2H), 6.62 (d, 1H, J = 3.6 Hz), 7.69 (d, 1H, J = 3.6 Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,57564-94-0, its application will become more common.

Reference:
Article; Davies, Nicholas G.M.; Browne, Helen; Davis, Ben; Drysdale, Martin J.; Foloppe, Nicolas; Geoffrey, Stephanie; Gibbons, Ben; Hart, Terance; Hubbard, Roderick; Jensen, Michael Rugaard; Mansell, Howard; Massey, Andrew; Matassova, Natalia; Moore, Jonathan D.; Murray, James; Pratt, Robert; Ray, Stuart; Robertson, Alan; Roughley, Stephen D.; Schoepfer, Joseph; Scriven, Kirsten; Simmonite, Heather; Stokes, Stephen; Surgenor, Allan; Webb, Paul; Wood, Mike; Wright, Lisa; Brough, Paul; Bioorganic and Medicinal Chemistry; vol. 20; 22; (2012); p. 6770 – 6789;,
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. 14394-70-8, name is 2-Chloro-5-methylpyrimidin-4-amine. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C5H6ClN3

[0257] A mixture of 2-cliloro-5-methylpyrimidin-4-amine (540 mg, 3.7 mmol), tot-butyl 4-(4-aminophenoxy)pirhoeridine-l-carboxylate (1.1 g, 3.7 mml) was suspended in acetic acid (20 mL) and heated at 70 C for 1 h. The mixture was allowed to cool to room temperature and acetic acid removed under reduced pressure. The residue was taken in water (20 mL) and neutralized to pH~7. The resulting solution was extracted with EtOAc (30 mL) and the organic layer separated. The organic layer was washed with brine, dried over MgStheta4 and filtered. The filtrate was concentrated in vacuo to afford the title compound (1.4 g, 95%) as a yellow solid.

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, 14394-70-8, 2-Chloro-5-methylpyrimidin-4-amine.

Reference:
Patent; TARGEGEN, INC.; WO2007/53452; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia