Category: pyrimidines

Reference of 99586-66-0 ,Some common heterocyclic compound, 99586-66-0, molecular formula is C6H5ClN4, 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.

General procedure: d) At rt, a solution of intermediate Xl (1 eq.) and an aryl halogenide VIII (1 to 2.5 eq.) in alcohol (nBuOH or EtOH, 0.08M to 0.1M) was treated with DIPEA (2 to Seq.) and irridiated in a microwave reactor or heated in an oil bath at 120-160C for 0.5 h to 6 d. Purification of intermediates and final products IX was carried out by flash chromatography,HPLCorSFC.

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. 99586-66-0, 2-Amino-4-chloro-6-methylpyrimidine-5-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; DU, Zhenxing; HINTERMANN, Samuel; HURTH, Konstanze; JACQUIER, Sebastien; LEHMANN, Hansjoerg; MOEBITZ, Henrik; SOLDERMANN, Nicolas; STOJANOVIC, Aleksandar; WO2015/10641; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 1337532-51-0 , The common heterocyclic compound, 1337532-51-0, name is 5-Bromo-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine, molecular formula is C7H7BrN4, 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 stirred solution of 4-benzyl- 1 -(4-bromo-3-fl uorophenyl)- 1 H- 1,2 ,4-triazol-5(4H)- one (0.520 g, 1.494 mmol, 1.0 equiv), was added bis(pinacolato)diboron (0.130 g, 1.494 mmol, 1.0 equiv), potassium acetate (0.440 g, 1.494 mmol, 3.0 equiv), and the mixture was degassed with Argon for 10 mi PdCI2(dppf)-CH2CI2 adduct (0.061 g, 0.075 mmol,0.05 equiv) was added and again degassed with Argon for 10 mm. The reaction mixture was stirred for 5h at 100 00 in a sealed vessel. The reaction mixture was cooled to room temperature, 5-bromo-7-methyl-7H- pyrrolo[2,3-d]pyrimidin-4-amine (0.340 g, 1.494 mmol, 1.0 equiv) and saturated aqueous NaHCO3 (5 mL) was added to the reaction mixture and Argon gas was bubbled through the mixture for 10 mi PdCI2(dppf)-CH2CI2 adduct (0.061 g, 0.075 mmol,0.05 equiv ) was added to the reaction mixture, the vessel was sealed and the reaction mixture was stirred overnight at 100 00 . The reaction mixture was cooled to room temperature and filtered through celite, the filtrate was dried over Na2SO4 and concentrated. The crude material was purified by flash column chromatography using silicagel column using 4-5 % MeOH in DCM as an eluent to obtain 1-(4-(4- ami no-7-methyl-7H-pyrrolo[2 ,3-d]pyrimidin-5-yl)-3-fluorophenyl)-4-benzyl- 1 H-i ,2,4-triazol- 5(4H)-one as off white solid (0.044 g, 7.1 %). LCMS (ES) m/z = 416.2 [M÷H]. 1H NMR (400 MHz, DMSO-d6) O ppm 3.74 (5, 3H), 4.91 (5, 2H), 6.03 (br.s, 2H), 7.33 – 7.41 (m, 6H), 7.48 (t, J = 9.2 Hz, 1H), 7.84 (t, J = 6.0 Hz, 2H), 8.14 (5, 1H), 8.42 (5, 1H). 99.79% of purity by HPLC 254 nM.

The synthetic route of 1337532-51-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; AXTEN, Jeffrey Michael; FAUCHER, Nicolas Eric; DAUGAN, Alain Claude-Marie; (110 pag.)WO2017/46738; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 330786-24-8, 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 330786-24-8, name is 3-(4-Phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine. This compound has unique chemical properties. The synthetic route is as follows.

Step 3. A suspension of 3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (400 mg, 1.3 mmol, 1.00 equiv), 2-(3-bromo-2,2-dimethylpropyl)-2,3-dihydro-1H-isoindole-1,3-dione (570 mg, 1.95 mmol, 1.50 equiv) and cesium carbonate (847 mg, 2.60 mmol, 2.00 equiv) in NMP (50 mL) was stirred at 100 C for 12 h under nitrogen atmosphere. It was quenched with water (150 mL). The resulting solution was extracted with ethyl acetate (5 x 30 mL). The organic layers were combined, dried over sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column eluting with dichloromethane/methanol (10 /1). This resulted in 280 mg (41%) of 2-(2-[[4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-2-methylpropyl)-2,3-dihydro-1H-isoindole-1,3-dione as a yellow oil.

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 330786-24-8, 3-(4-Phenoxyphenyl)-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: 4316-98-7, 6-Chloro-4,5-diaminopyrimidine, 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 C4H5ClN4, blongs to pyrimidines compound. Computed Properties of C4H5ClN4

8-(4-((1H-pyrazol-1-yl)methyl)benzyl)-6-chloro-7H-purineCombined 2-[4-(1H-pyrazol-1-ylmethyl)phenyl]acetic acid (Fichert, Thomas; Yazdanian, Mehran; Proudfoot, John R. Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, 4 p. 719-722)(400.00 mg; 1.85 mmol; 1.00 eq.) and 6-chloropyrimidine-4,5-diamine (267.42 mg; 1.85 mmol; 1.00 eq.) in POCl3 (5.00 ml). Heated the reaction to 90 C. for 3 hours. Let the reaction cool to rt. Concentrated. Diluted with water, neutralized with sat?d NaHCO3, and extracted with ethyl acetate. Combined organics, dried with MgSO4, filtered, and concentrated. Purified by Biotage silica gel column to afford 8-(4-((1H-pyrazol-1-yl)methyl)benzyl)-6-chloro-7H-purine (319 mgs; 53%). MS (M+H)+ found for C16H13ClN6 : 325.0.

The synthetic route of 4316-98-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Global Blood Therapeutics, Inc.; Li, Zhe; Xu, Qing; Yu, Chul; Yee, Calvin; Gwaltney,, II, Stephen L.; Metcalf, Brian W.; Richards, Steven; Lardy, Matthew A.; Setti, Lina; Sham, Hing; US2015/315198; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 13036-57-2, 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.13036-57-2, name is 2-Chloro-4-methylpyrimidine, molecular formula is C5H5ClN2, molecular weight is 128.56, as common compound, the synthetic route is as follows.

Step E: 2-Propen-1-yl [3-[(2-chloro-4-pyrimidinyl)acetyl]-2-(methyloxy)phenyl]carbamate; To a solution of methyl 2-(methyloxy)-3-{[(2-propen-1-yloxy)carbonyl]amino}benzoate (123 g, 464 mmol,) in dry THF (800 mL) at -10 C., LiHMDS (1M in THF, 1440 mmol, 1440 mL) was added dropwise and the solution was allowed to stir for 1 h at 0 C. A solution of 2-chloro-4-methylpyrimidine (72 g, 560 mmol) in THF (150 mL) was then added dropwise to the solution of ester and base at 0 C. over 20 min. The solution was allowed to stir 1 h at rt. TLC showed the reaction was complete. The reaction was quenched by addition of the saturated aqueous NH4Cl (800 mL) at 0 C. The reaction mixture was extracted with EtOAc (1 L×3). The combined organic layers were washed with water and brine successively, dried over Na2SO4, filtered and concentrated under reduced pressure to give the crude product, which was purified by flash column on silica gel, eluting with DCM. This solution was evaporated to obtain a solid. The orange solid was triturated with a small amount of EtOAc and filtered, rinsing with diethyl ether to give the title compound of Step E (109.9 g, 67.8% yield). 1H NMR (400 MHz, CDCl3) delta ppm 13.64-13.68 (br, 1H), 8.38 (d, J=5.3 Hz, 1H), 8.15-8.21 (m, 1H), 7.31-7.39 (m, 2H), 7.15-7.18 (m, 1H), 6.87 (d, J=5.3 Hz, 1H), 6.19 (s, 1H), 5.92-6.15 (m, 1H), 5.23-5.40 (m, 2H), 4.66-4.70 (m, 2H), 3.76 (s, 3H).

The chemical industry reduces the impact on the environment during synthesis 13036-57-2, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Adams, Jerry Leroy; Dickerson, Scott Howard; Johnson, Neil W.; Kuntz, Kevin; Petrov, Kimberly; Ralph, Jeffrey M.; Rheault, Tara Renae; Schaaf, Gregory; Stellwagen, John; Tian, Xinrong; Uehling, David Edward; Waterson, Alex Gregory; Wilson, Brian; US2009/298815; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 5305-59-9 , The common heterocyclic compound, 5305-59-9, name is 6-Chloropyrimidin-4-amine, molecular formula is C4H4ClN3, 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.

General procedure: A mixture of 3-chloro-4-(3-fluorobenzyloxy)aniline (5.00 g, 19.86 mmol) and compound 2 (4.17 g, 16.55 mmol) with two drops concd HCl in n-BuOH (30 mL) was heated at 110 C and kept stirring for 3 h. As the mixture cooled, the formed yellow solid was filtered through washing with n-BuOH followed by saturated NaHCO3 aqueous solution. After being dried overnight at vacuum drying oven at 40 C, the solid was purified by column chromatography on silica gel eluted with EtOAc/petroleum ether (1:2) to give 3 as a yellowish green solid (6.18 g, 13.24 mmol, 80% yield).

The synthetic route of 5305-59-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Li, Siyuan; Guo, Chunying; Zhao, Hongli; Tang, Yun; Lan, Minbo; Bioorganic and Medicinal Chemistry; vol. 20; 2; (2012); p. 877 – 885;,
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. 1260088-72-9, name is 2,4-Dichloro-7,7-dimethyl-5,7-dihydrofuro[3,4-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C8H8Cl2N2O

General procedure: A mixture of 2,4-dichloro-7,7-dimethyl-5,7-dihydrofuro[3,4-d]pyrimidine7 (257mg, 1.173 mmol), 1H-pyrazolo[4,3-c]pyridin-3-amine (291 mg, 1.735 mmol), N,N-diisopropylethylamine (0.40 mL, 2.3 mmol) and N,N-dimethylformamide (4.0 mL) was heated at 70 C for 2 hours. The reaction mixture was diluted with ethyl acetate, washed with water (2x) and brine, dried over magnesium sulfate, filtered, and evaporated in vacuo. The crude product was purified via flash chromatography on silica gel (24 silica, solvent gradient: 0-100% ethyl acetate in dichloromethane followed by 10% methanol indichloromethane) to yield 176.7 mg of the title compound.

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, 1260088-72-9, 2,4-Dichloro-7,7-dimethyl-5,7-dihydrofuro[3,4-d]pyrimidine.

Reference:
Article; Hanan, Emily J.; Baumgardner, Matt; Bryan, Marian C.; Chen, Yuan; Eigenbrot, Charles; Fan, Peter; Gu, Xiao-Hui; La, Hank; Malek, Shiva; Purkey, Hans E.; Schaefer, Gabriele; Schmidt, Stephen; Sideris, Steve; Yen, Ivana; Yu, Christine; Heffron, Timothy P.; Bioorganic and Medicinal Chemistry Letters; vol. 26; 2; (2016); p. 534 – 539;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 4316-94-3, 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 4316-94-3, name is 6-Chloro-5-nitropyrimidin-4-amine. This compound has unique chemical properties. The synthetic route is as follows.

2-[4-(4-Trifluoromethylpyridin-2-yloxy)-phenyl]-ethanol (product from Step 1; 400 mg, 1.4 mmol) was dissolved in DMSO (10 mL), treated with 95% NaH (36 mg, 1.5 mmol) and the mixture was warmed to 50-600C to produce a clear solution. Upon cooling the mixture was treated with 4-amino-5-nitro-6-chloropyrimidine (260 mg, 1.5 mmol) and heated at 450C for 6 h. After cooling the mixture was poured into H2O (60 mL) and the precipitate was collected by suction filtration, washed with H2O and air-dried on the filter: 1H NMR (300 MHz, CDCl3) delta 8.39 (s, IH), 8.33 (s, IH), 8.18 (s, IH), 7.38 (m, 2H), 7.15 (m, 4H), 4.69(t, / = 6.8 Hz, 2H), 3.15 (t, 6.6 Hz, 2H). This material was used in the next step without further purification.

According to the analysis of related databases, 4316-94-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DOW AGROSCIENCES LLC; BREWSTER, William; DEMETER, David; ERICKSON, W.; LOWE, Christian; KLITTICH, Carla; NUGENT, Jaime; RIEDER, Brent; SIDDALL, Thomas; YAO, Chenglin; YERKES, Carla; ZHU, Yuanming; WO2011/25505; (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.3764-01-0, name is 2,4,6-Trichloropyrimidine, molecular formula is C4HCl3N2, molecular weight is 183.42, as common compound, the synthetic route is as follows.Quality Control of 2,4,6-Trichloropyrimidine

The 6-chloro-4-(2-difluoromethylbenzimidazol-l-yl)-2-morpholinopyrimidine used as a starting material was prepared as follows :-; Under an atmosphere of nitrogen, a solution of morpholine (13.06 ml) in methylene chloride (100 ml) was added dropwise over 15 minutes to a stirred mixture of 2,4,6-trichloropyrimidine (27.52 g), triethylamine (22.1 ml) and methylene chloride (200 ml) that was cooled to a temperature between 5C and 15C. The resultant mixture was allowed to warm to ambient temperature and was stirred for 2 hours. The mixture was washed with an aqueous brine solution. The organic solution was dried over magnesium sulphate and evaporated. The residue was purified by column chromatography on silica using increasing proportions of ethyl acetate added to a 1 : 1 mixture of isohexane and methylene chloride as eluent. There was thus obtained 4,6-dichloro-2-morpholinopyrimidine (6.82 g); NMR Spectrum: (DMSOd6) 3.64-3.71 (m, 8H), 6.97 (s, IH); Mass Spectrum: M+H+ 234.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,3764-01-0, 2,4,6-Trichloropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; BUTTERWORTH, Sam; GRIFFEN, Edward, Jolyon; HILL, George, Beresford; PASS, Martin; WO2008/32089; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 10397-13-4, Adding some certain compound to certain chemical reactions, such as: 10397-13-4, name is 4-(4,6-Dichloropyrimidin-2-yl)morpholine,molecular formula is C8H9Cl2N3O, 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 10397-13-4.

A mixture of 2-difluoromethyl-lff-benzimidazole (0.168 g), 4,6-dichloro-2-morpholin- 4-yl-rhoyrimidine (0.233 g), sodium hydrogen carbonate (0.168 g) and DMA (5 ml) was stirred under nitrogen at 900C for 20 hours, filtered and evaporated. The product was purified by chromatography on silica eluting with increasing proportions of ethyl acetate in dichloromethane/iso-hexane (1:1). There was thus obtained l-(6-chloro-2-morpholin-4-yl- pyrimidin-4-yl)-2-(difluoromethyl)benzoimidazole (0.075 g); NMR Spectrum: (DMSOd6) 3.70 (m, 4H), 3.78 (m, 4H), 7.20 (s, IH), 7.39-7.72 (m, 3H), 7.84 (d, IH), 7.90 (d, IH); Mass Spectrum: M+H+ 366.

According to the analysis of related databases, 10397-13-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; BUTTERWORTH, Sam; GRIFFEN, Edward, Jolyon; HILL, George, Beresford; PASS, Martin; WO2008/32036; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia