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.3073-77-6, name is 2-Amino-5-nitropyrimidine, molecular formula is C4H4N4O2, molecular weight is 140.1, as common compound, the synthetic route is as follows.Product Details of 3073-77-6

EXAMPLE 92. Synthesis of 4-f5-Nitro-Pyrimidin-2-ylaininoVN-(2-PyrroIidin-l-yl- ethvD-Benzenesulfonamide (Intermediate 44)44[02871 A mixture of 2-amino-5-nitropyrimdin (7.14 mmol, 1.0 equiv), intermediate 43 (Example 91) (10.71 mmol, 1.5 equiv), Pd(OAc)2 (0.357 mmol, 0.05 equiv), Xantphos (0.714 mmol, 0.1 equiv) and potassium-tert-butoxide (14.28 mmol, 2.0 equiv) was suspended in 40 mL of dioxane and refluxed at 1000C under an argon atmosphere for 18 h. The mixture was allowed to cool to room temperature, filtered and washed with DCM. The filtrate was concentrated and the crude product precipitated out using EtOAc/Hexanes (1:5 v/v) to afford the title compound as a yellow solid (1.67g, 60%). MS (ES+): m/z = 393 (M-J-H)+. LC retention time: 1.79 min.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,3073-77-6, 2-Amino-5-nitropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; TARGEGEN, INC.; WO2008/8234; (2008); 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. 7752-82-1, name is 5-Bromopyrimidin-2-amine. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C4H4BrN3

To a solution of 45 (5.0 g, 28.7 mmol) in THF (50 mL) are added di-tert-butyi dicarbonate (13.8 g, 63.2 rnrnoi), TEA (12.0 rnL, 86 mmol), and DMAP (360mg, 2.87 mmol). After stirring at 60 C for 16 hour, the mixture is concentrated and purified by silica gel column chromatography (EA:PE = 1:5) to give 46 as a while solid (9.0 g, 84% yield). (MS: [M+HI 374.1)

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, 7752-82-1, 5-Bromopyrimidin-2-amine.

Reference:
Patent; IMMUNE SENSOR, LLC; THE BOARD OF REGENTS OF THE UNIVERSITY OF TEXAS SYSTEM; ZHONG, Boyu; SUN, Lijun; SHI, Heping; LI, Jing; CHEN, Chuo; CHEN, Zhijian; (270 pag.)WO2017/176812; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 49844-90-8, 4-Chloro-2-(methylthio)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, 49844-90-8, blongs to pyrimidines compound. Application In Synthesis of 4-Chloro-2-(methylthio)pyrimidine

Example 7 Synthesis of (4-Hydroxy-piperidin-1-yl)-(4-{4-[4-(4-methyl-thiophen-3-yl)-indol-1-yl]-pyrimidin-2-ylamino}-cyclohexyl)-methanone (Compound 7) To a suspension of NaH (7.59 g, 60%) in DMF (200 mL) under N2 was added 4-bromo-indole in portions, and the mixture stirred for 15 min at 0 C. To this was added 4-chloro-2-methylsulfanyl-pyrimidine (15.45 mL) in portions, and the reaction mixture stirred for 30 min at 0 C., then allowed to warm to RT with stirring for another 30 min. The reaction mixture was then quenched with cold water at 0 C., and the resulting suspension filtered, washed with water, and dried to obtain a crude product (41.01 g). The crude product (21.90 g) was chromatographed on silica, eluted with hexane:EtOAc (900:100) to provide an off-white solid (16.4 g). The solid was heated in EtOH on a steam bath, crystallized, filtered, and dried to provide 4-bromo-1-(2-methylsulfanyl-pyrimidin-4-yl)-1H-indole.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,49844-90-8, its application will become more common.

Reference:
Patent; Gong, Leyi; Jahangir, Alam; Reuter, Deborah Carol; US2010/160360; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 1005-39-6, 2-(Methylthio)pyrimidine-4,6-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, Product Details of 1005-39-6, blongs to pyrimidines compound. Product Details of 1005-39-6

740 mg (2.70 mmol) of ethyl 2-(4-cyano-2-methoxybenzylidene)-3-oxobutanoate and 422 mg (2.70 mmol) of 2-(methylthio)pyrimidine-4,6-diamine are dissolved in 5 ml of isopropanol and heated under reflux under argon for 12 h. The mixture is filtered and the remaining solid is washed with isopropanol. 395 mg (35% of theory) of the title compound are obtained as a white solid. LC-MS (method 1): Rt=2.06 min; [M+H]+=412 1H-NMR (400 MHz, DMSO-d6): delta=1.02 (t, 3H), 2.33 (s, 3H), 2.36 (s, 3H), 3.86 (q, 2H), 3.90 (s, 3H), 5.19 (s, 1H), 6.27 (s, 2H), 7.36 (s, 2H), 7.47 (s, 1H), 7.92 (dd, 1H), 9.58 (s, 1H).

The synthetic route of 1005-39-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER HEALTHCARE AG; US2010/35902; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 2380-63-4, name is 1H-Pyrazolo[3,4-d]pyrimidin-4-amine. A new synthetic method of this compound is introduced below., HPLC of Formula: C5H5N5

Step 1. To a solution of 1H-pyrazolo[3,4-d]pyrimidin-4-ylamine (3.0 g, 22.20 mmol, 1.0 eq) in DMF (30 mL), NIS (6.7g, 24.42 mmol, 1.1 eq) was added at room temperature. The reaction mixture was stirred overnight at 60 C. The reaction mixture was cooled to roomtemperature and 10 % aq. NaHCO3 (150 mL) was added to the reaction mixture. The solid was filtered and re-crystallization from DMF solvent to give 3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-ammne (4.0 g, 69 % in yield).

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, 2380-63-4, 1H-Pyrazolo[3,4-d]pyrimidin-4-amine.

Reference:
Patent; PRINCIPIA BIOPHARMA INC.; BABLER, Martin; GERRITSEN, Mary E.; WO2014/22569; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 57489-77-7, 5,7-Dichloropyrazolo[1,5-a]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, Computed Properties of C6H3Cl2N3, blongs to pyrimidines compound. Computed Properties of C6H3Cl2N3

General procedure: To a well stirred 8-aminoquinoline (1 mmol) indry DMF (5 mL), sodium hydride (1.2 mmol, 60% in mineral oil) was added at 0 C.After 10 min stirring, the corresponding heterocyclic chloro compound (1.2mmol) was added and stirred for 10 min at rt then heated at 60 C for 5-12 h.Upon completion, the reaction mixture was poured into crushed ice and theresulting solid was filtered, washed with water and dried under vacuum. Thesolid was triturated with methanol and dried under vacuum to afford targetcompound as a solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,57489-77-7, 5,7-Dichloropyrazolo[1,5-a]pyrimidine, and friends who are interested can also refer to it.

Reference:
Article; Kannan, Murugan; Raichurkar, Anandkumar V.; Khan, Fazlur Rahman Nawaz; Iyer, Pravin S.; Bioorganic and Medicinal Chemistry Letters; vol. 25; 5; (2015); p. 1100 – 1103;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 63155-43-1, Adding some certain compound to certain chemical reactions, such as: 63155-43-1, name is 2-(4,6-Dichloropyrimidin-2-yl)acetonitrile,molecular formula is C6H3Cl2N3, 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 63155-43-1.

To a solution of 2-(4,6-dichloropyrimidin-2-yl)acetonitrile (2.2 g, 11.7 mmol) and triethylamine (3.0 mL, 20.8 mmol) in ethyl acetate / MeOH (1/1, 40 mL) was added 10% Pd/C (400 mg) and the solution was vigorously stirred for 2.5 hours under H2 atmosphere (1 atm). The reaction was filtered through celite and washed the celite with MeOH. The combined filtrates were concentrated under reduced pressure and purified by flash chromatography (5i02, PE / EA = 1/1) to give the 2-(pyrimidin-2-yl)acetonitrile as a pale red liquid (618 mg, 54%). MS [MH] calcd for C6H5N3 120.1, found 120.1.

According to the analysis of related databases, 63155-43-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NATIONAL INSTITUTE OF BIOLOGICAL SCIENCES, BEIJING; HUANG, Niu; PENG, Shiming; (87 pag.)WO2016/206573; (2016); 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.20781-06-0, name is 2,4-Diaminopyrimidine-5-carboxaldehyde, molecular formula is C5H6N4O, molecular weight is 138.1273, as common compound, the synthetic route is as follows.Safety of 2,4-Diaminopyrimidine-5-carboxaldehyde

EXAMPLE 111 6-Pyridin-2-yl-pyrido[2,3-d]pyrimidine-2,7-diamine The procedure of Example 1 was followed to react 0.84 mL of 2-pyridylacetonitrile and 1.0 g of 2,4-diamino-5-pyrimidinecarboxaldehyde to afford the title compound, mp 312-321 C. Analysis calculated for C12 H10 N6.0.07 H2 O: C, 60.18; H, 4.27; N, 35.09. Found: C, 60.46; H, 4.34; N, 34.70.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,20781-06-0, 2,4-Diaminopyrimidine-5-carboxaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; Blankley; Clifton John; Doherty; Annette Marian; Hamby; James Marino; Panek; Robert Lee; Schroeder; Mel Conrad; Showalter; Howard Daniel Hollis; Connolly; Cleo; US5733913; (1998); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 14080-59-2, 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. 14080-59-2, name is 4-Chlorothieno[2,3-d]pyrimidine, molecular formula is C6H3ClN2S, 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.

Examples 308 and 309 Synthesis of 6-bromo-4-chlorothieno[2,3-d]pyrimidine and 6-bromo-2-butyl-4-chlorothieno[2,3-d]pyrimidine n-BuLi (1.6 M in hexane, 1.9 ml, 2.5 mmol) in THF (8 ml) was cooled to -78 C. 4-Chlorothieno[2,3-d]pyrimidine (0.34 g, 2.0 mmol) was dissolved in THF (2 ml) and slowly added to the reaction mixture over 5 minutes. After 20 min, CBr4 (0.73 g, 2.2 mmol) in THF (3 ml) was slowly added to the reaction mixture. The temperature was maintained at -78 C. for 20 minutes and then warmed to room temperature for 2 hours. The mixture was poured into water and extracted with chloroform, dried over sodium sulfate, and concentrated in vacuo. The crude residue was purified by silica gel chromatography (EtOAc/hexane 40:1) to yield two pure compounds a white solid (example 203: 0.13 g, 25% and example 204: 0.16 g, 26%).

According to the analysis of related databases, 14080-59-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Katholieke Universiteit Leuven, K.U. Leuven R&D; Herman, Jean; Louat, Thierry; US2014/88088; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 2435-50-9, 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. 2435-50-9, name is Pyrimidine-4-carbaldehyde. A new synthetic method of this compound is introduced below.

General procedure: A suspension of methyl 2-(2-aminoethyl)-1 ,3-thiazole-4-carboxylate (5) (1.96 g, 10.52 mmol), 1 H- benzimidazole-2-carbaldehyde (2.31 g, 15.79 mmol) and DIPEA (1.83 ml, 10.52 mmol) in MeOH (100 ml) was stirred at room temperature for 12 h. The reaction mixture was cooled to 0C, NaBH4 (0.597 g, 15.79 mmol) was added and the mixture stirred at room temperature for 2 h. The reaction mixture was concentrated in vacuo and the residue dissolved in EtOAc (100 ml) and washed with saturated NC03 (2 x 50 ml). The combined aqueous layers were extracted with EtOAc (3 x 50 ml) and the combined organic layers dried (MgS04), filtered and evaporated in vacuo. Purification by flash column chromatography (KP- NH, eluting with a gradient of 0-10% MeOH / DCM) afforded the title compound (1.4 g, 38%, 90% purity) as a tan solid. 1 H-NMR (Methanol-d4, 250 MHz): d[ppm]= 8.27 (s, 1 H), 7.60 – 7.49 (m, 2H), 7.29 – 7.17 (m, 2H), 4.09 (s, 2H), 3.92 (s, 3H), 3.26 (t, J = 6.3 Hz, 2H), 3.10 (t, J = 6.8 Hz, 2H) HPLCMS (Method A): [m/z]: 317 [M+H]+In a similar fashion to general procedure 3, 2-(2-aminoethyl)-N-benzyl-1 ,3-thiazole-4-carboxamide (104) (150 mg, 0.574 mmol), pyrimidine-4-carbaldehyde (61 mg , 0.564 mmol), TEA (0.79 ml, 6 mmol) in MeOH (2 ml) at room temperature for 6 h, followed by addition of NaBH; (32 mg, 0.846 mmol) gave the title compound (150 mg, 75%) as an brown oil after purification by flash column chromatography (eluting with a gradient of 5% MeOH in DCM). 1 H-NMR (CDCb, 400 MHz): d[ppm]= 9.05 (d, J = 1.3 Hz, 1 H), 8.63 (d, J = 5.2 Hz, 1 H), 8.04 (s, 1 H), 7.69 (s, 1 H), 7.39 – 7.27 (m, 6H), 4.66 (d, J = 6.1 Hz, 2H), 3.94 (s, 2H), 3.20 (t, J = 6.3 Hz, 2H), 3.09 (t, J = 6.6 Hz, 2H), HPLCMS (Method L): [m/z]: 354.0 [M+H]+

At the same time, in my other blogs, there are other synthetic methods of this type of compound,2435-50-9, Pyrimidine-4-carbaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; VIFOR (INTERNATIONAL) AG; DUeRRENBERGER, Franz; BUHR, Wilm; BURCKHARDT, Susanna; BURGERT, Michael; KALOGERAKIS, Aris; REIM, Stefan; MANOLOVA, Vania; BOYCE, Susan; YARNOLD, Christopher John; PENA, Paula; SHEPHERD, Jon; LECCI, Cristina; JARJES-PIKE, Richard; SCOTT, John; (416 pag.)WO2017/68089; (2017); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia