Pyrimidines

Related Products of 461-98-3, 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.461-98-3, name is 2,6-Dimethylpyrimidin-4-amine, molecular formula is C6H9N3, molecular weight is 123.16, as common compound, the synthetic route is as follows.

The mixture of 4-bromo-7-fluoro-2-(2,6-dichlorophenyl)-lH-imidazo[4,5-c]pyridine (50 mg, 0.14 mmol), 2,6-dimethylpyrimidine-2 -amine (22 mg, 0.18 mmol), Pd2(dba)3 (4 mg, 0.0040 mmol), XantPhos (2 mg, 0.002 mmol), Cs2C03 (90 mg, 0.28 mmol) in 1,4-Dioxane (10 mL) and DME (2 mL) was degassed with N2 for 1 min. The resulting mixture was irradiated in a microwave reactor at 170 C for 2 hrs and cooled to room temperature. The mixture was filtered with Celite and the filtrate was concentrated and purified by prep-HPLC (Gilson GX 281, Shim-pack PRC-ODS 250 mm x 20 mm x 2, gradient: CH3CN / 10 mm/L NH4HCO3, 17 min) to give the desired product (27 mg, yield: 48%). ¾ NMR (DMSO- 6, 500 MHz): delta 8.30 (d, J = 6.0 Hz, 1H), 7.95 (s, 1H), 7.61 (m, 4H), 2.39 (s, 3H), 2.34 (s, 3H). LC-MS(ESI) m/z: 404.4 [M+H+].

Statistics shows that 461-98-3 is playing an increasingly important role. we look forward to future research findings about 2,6-Dimethylpyrimidin-4-amine.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; LAI, Yingjie; LIANG, Jun; MAGNUSON, Steven R.; TSUI, Vickie H.; ZHANG, Birong; ROBARGE, Kirk; WO2011/113802; (2011); A2;,
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Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 49721-45-1, Pyrimidine-4,5,6-triamine sulfate, 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 C4H9N5O4S, blongs to pyrimidines compound. Computed Properties of C4H9N5O4S

EXAMPLE 2 4-Amino-7-(3-chlorophenyl)pteridine To a suspension of 5.2 g. of selenous acid in 40 ml. of dioxane was added 3.09 g. of m-chloroacetophenone. The mixture was refluxed for 4 hours, filtered and the filtrate was evaporated to dryness. A hot suspension of 3.90 g. of this glyoxal in 15 ml. of ethanol was added to a stirred suspension of 3.26 g. of 4,5,6-triaminopyrimidine sulfate and the condensation product was worked up as in Example 1 to produce 1.6 g. of 4-amino-7-(3-chlorophenyl)pteridine, melting at 260-4 degrees C. This compound was tested at 100 mg/kg by the procedure of Example 1, giving the excretion rates shown in Table I.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,49721-45-1, Pyrimidine-4,5,6-triamine sulfate, and friends who are interested can also refer to it.

Reference:
Patent; Abbott Laboratories; US4187307; (1980); A;,
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Pyrimidine – Wikipedia

Synthetic Route of 10320-42-0, 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 10320-42-0, name is 2-Chloro-5-nitropyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

first step:A dry 50 mL reaction jar was vacuumed three times with nitrogen.After adding N-methylaniline (107 mg, 1.0 mmol, 1.0 equiv) to the reaction jar,Add 10.0 mL of dried acetonitrile and stir until N-methylaniline is completely dissolved.Then 2-chloro-5-nitropyrimidine (0.1593 g, 1.0 mmol, 1.0 equiv) was added to the reaction flask.The entire mixture was reacted under nitrogen pressure for 4-5 hours.The reaction detects the progress of the reaction by TLC.The reaction can be stopped if it is detected that all the aniline is completely reacted.The experimental treatment is to drain the solution in the reaction;The solute in the reaction flask was dissolved with ethyl acetate.And transferred to a 100 mL round bottom flask,Add 2 mL (200-300 mesh) of silica gel to the round bottom flask for spin-drying (petroleum ether and acetic acid B)Ester) over silica gel in the column.The intermediate product was pale yellow crystals N-methyl-5-nitro-N-phenylpyrimidin-2-amine (197 mg, 86% yield).

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 10320-42-0, 2-Chloro-5-nitropyrimidine.

Reference:
Patent; Jinan University; Feng Pengju; Chen Tianfeng; Chen Junfeng; Huang Yifeng; (25 pag.)CN108148005; (2018); A;,
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Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 32779-37-6, 2,5-Dibromopyrimidine, 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, Recommanded Product: 2,5-Dibromopyrimidine, blongs to pyrimidines compound. Recommanded Product: 2,5-Dibromopyrimidine

5-bromo-N-(3-chloro-4-(difluoromethoxy)phenyl)pyrimidin-2-amine To a solution of 3-chloro-4-(difluoromethoxy)aniline (0.814 g, 4.20 mmol) in butan-1-ol (10 mL), were added DIPEA (2.203 mL, 12.61 mmol) and 2,5-dibromopyrimidine (1 g, 4.20 mmol). The reaction mixture was stirred at 120 C. for 12 h and concentrated. The crude product was purified by flash chromatography on silica gel using 3% ethyl acetate in petroleum ether to give 5-bromo-N-(3-chloro-4-(difluoromethoxy)phenyl)pyrimidin-2-amine (0.8 g, 64%). LCMS (ES-ES), m/z 349.98.

The synthetic route of 32779-37-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; King, Dalton; Macor, John E.; Olson, Richard E.; Iwuagwu, Christiana I.; Karageorge, George N.; US2013/79338; (2013); A1;,
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Application of 1820-81-1, 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.

Example 15 N4-[(trans-4-aminocyclohexyl)methyl]-5-chloro-N2-[2-(trifluoromethoxy)benzyl]pyrimidine-2,4-diamine To a suspension of 5-chlorouracil (15.0 g, 102.4 mmol) in POCl3 (50 mL, 326.1 mmol) was added N,N-diethylaniline (7.5 mL). The reaction mixture was heated at 110 C. for 24 h. The reaction mixture was cooled to room temperature and concentrated in vacuo to about 25 mL. The resulting residue was then poured into ice and stirred until all the ice melted. The aqueous layer was extracted with ether (*3). The combined organic phase was dried over anhydrous Na2SO4 and concentrated in vacuo. The resulting residue was distilled under vacuum at ~90 C. to afford 12.5 g (81%) of 5-chloro-2,4-dichloropyrimidine.

The chemical industry reduces the impact on the environment during synthesis 1820-81-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Boehringer Ingelheim Pharmaceuticals, Inc.; US2006/25433; (2006); A1;,
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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

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;,
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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;,
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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;,
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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;,
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