Pyrimidines

Adding a certain compound to certain chemical reactions, such as: 145783-15-9, 4,6-Dichloro-2-(propylthio)pyrimidin-5-amine, 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, name: 4,6-Dichloro-2-(propylthio)pyrimidin-5-amine, blongs to pyrimidines compound. name: 4,6-Dichloro-2-(propylthio)pyrimidin-5-amine

3) Operation process(1) Add 18L of ethylene glycol and 9.335kg of SM1 to the 100L reactor.12kg SM2 and 16.529kg triethylamine,Stir and mix;(2) heating the reaction solution to 90 ~ 100 C, the reaction liquid solid dissolved, the color is a yellow clear solution; maintaining this temperature for 8 to 10 hours;(3) TLC detection, the developing agent is ethyl acetate: methanol = 1:1, the color developing agent is ninhydrin ethanol solution, and the color is baked at 150 C;Lower the reaction solution to below 50 C,The reaction solution is a dark brown clear solution;The reaction solution was poured into a 200 L reaction vessel containing 50 L of ethyl acetate and 50 L of water under stirring at room temperature;The 100 L reaction kettle was rinsed with 10 L of ethyl acetate and 10 L of purified water.The eluent was poured into a 200 L reaction kettle; stirred at room temperature for 30 minutes; the stirring was stopped, and the layer was allowed to stand.Divide the lower aqueous phase;(4) Add 60 L of purified water to the upper organic phase, stir at room temperature for 30 minutes; stop stirring, let stand for stratification, and separate the lower layer.water box;(5) Transfer the upper organic phase to a 500L reactor and heat to 60-70 C with stirring; in addition, 180 L of isooctane pre-Heat to 60 ~ 70 C, added to the reaction flask;(8) After adding, slowly cool down to room temperature with stirring and firstly cool to 35-45 C (solid precipitation temperature about 30-35 C).Slowly cool down to 20 ~ 30 C; keep stirring at 20 ~ 30 C for 1 hour, and then slowly reduce the temperature to 0 ~ 10 C;(8) stirring at 0 to 10 C for 2 hours;(9) Centrifugal filtration, the reaction kettle and filter cake are mixed with 12 L of ethyl acetate pre-cooled to 0-10 C and 36 L of isooctane.Rinsing(10) The filter cake is dried under vacuum at 45-55 C for 12 to 16 hours to obtain a white powder of Im-1, weighing 11 kg, yield80%.

The synthetic route of 145783-15-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hebei Kaiwei Pharmaceutical Co., Ltd.; Pang Yuning; (23 pag.)CN108276417; (2018); A;,
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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 1780-26-3, name is 2-Methyl-4,6-dichloropyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Formula: C5H4Cl2N2

[0059] Synthesis ofS5: ethyl 2-aminothiazole-5-carboxylate (1.0 g, 5.8 mmol) and 4,6- dichloro-2-methylpyrimidine (0.95 g, 5.8 mmol) were added to an oven dried flask. (0113) Dimethylformamide (20 mL) was then added. The reaction mixture was then cooled to 0 C, and sodium hydride (0.510 g, 12.8 mmol) was added. The reaction was allowed to warm to room temperature and stirred for an additional 3 hours. Excess base was quenched using ammonium chloride. The reaction was then suspended in water and filtered. After drying, the S5 was obtained as a white solid (1.4g, 81% yield). Spectral data: 1H NMR (400 MHz, DMSO-d6) delta 12.30 (s, 1H), 8.07 (s, 1H), 6.88 (s, 1H), 4.24 (q, J = 7.1 Hz, 2H), 2.54 (s, 3H), 1.26 (t, J = 7.1 Hz, 3H); 13C NMR (126 MHz, dmso) delta 167.85, 162.83, 161.96, 159.07, 157.88, 145.84, 122.02, 104.11, 61.22, 25.61,14.70; HRMS-ESI (m/z): [M + H]+ calcd for CnHnClN402S, 299.0364; found 299.0371.

With the rapid development of chemical substances, we look forward to future research findings about 1780-26-3.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF MICHIGAN; SOELLNER, Matthew, B.; PHADKE, Sameer; MERAJVER, Sofia, D.; (60 pag.)WO2017/87818; (2017); A1;,
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In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 127958-10-5, name is 2-Methyl-4-phenylpyrimidine-5-carboxylic acid, the common compound, a new synthetic route is introduced below. Computed Properties of C12H10N2O2

Example 17: To a mixture of A-14 (135 mg, 0.63 mmol), B-1 (150 mg, 0.53 mmol) and DIPEA (273 mu, 1 .60 mmol) in dry ACN (2.0 mL) is added CIP (191 mg, 0.68 mmol) and the mixture is stirred at RT for 2 days. ACN/H20 is added and the mixture is purified by prep. HPLC-MS (using a solvent gradient H20/ACN with NH4OH) to afford 133 mg of Example 17. ESI-MS: 445 [M+Na]+; HPLC (Rt): 1 .04 min (method G).

The synthetic route of 127958-10-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; RIETHER, Doris; FERRARA, Marco; HEINE, Niklas; LESSEL, Uta; NICHOLSON, Janet Rachel; PEKCEC, Anton; SCHEUERER, Stefan; (69 pag.)WO2017/178341; (2017); A1;,
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Electric Literature of 99586-66-0, Adding some certain compound to certain chemical reactions, such as: 99586-66-0, name is 2-Amino-4-chloro-6-methylpyrimidine-5-carbonitrile,molecular formula is C6H5ClN4, 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 99586-66-0.

General procedure: To a solution of 7a (80mg, 0.18mmol, 1 equiv), 4-amino-6-chloropyrimidine-5-carbonitrile (31mg, 0.2mmol, 1.1 equiv) in BuOH was added DIPEA (0.06mL, 0.36mmol, 2 equiv). The mixture was reacted under microwave at 130C for 20min. After completion, the solvent was removed under reduced pressure. The residue was redissolved in CH2Cl2. The crude was further purified via silica gel chromatography to give compound 8a as white solid (81mg, 80%).

According to the analysis of related databases, 99586-66-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wei, Manman; Zhang, Xi; Wang, Xiang; Song, Zilan; Ding, Jian; Meng, Ling-Hua; Zhang, Ao; European Journal of Medicinal Chemistry; vol. 125; (2017); p. 1156 – 1171;,
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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. 31058-83-0, name is 6-Chloro-N,N-dimethylpyrimidin-4-amine. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 31058-83-0

Example 33: N.N-Dimethyl-e-KIS.eRVe-tP-iS-methyl-l ^^-oxadiazol-S- l)phenyl]carbonyl}-3,8-diazabicyclo[4.2.0]oct-3-yl]pyrimidin-4-amine.A mixture of Intermediate 12 (50 mg, 0.17 mmol), 2-chloro-4,6- dimethylpyrimidine (24 mg, 0.17 mmol) and DIPEA (0.87 mL, 0.5 mmol) in ACN (1 mL) was heated in the microwave at 200 C for 2 h. The mixture was concentrated in vacuo and chromatography (Hex to 100% EtOAc/Hex) to afford the desired product as a pale yellow foam (39 mg, 55%). MS (ESI) mass calculated for C22H25N7O2, 419.2; m/z found, 420.2. 1 H NMR (500 MHz, CDCI3): 8.15 (s, 1 H), 8.12 – 8.04 (m, 1 H), 7.59 – 7.50 (m, 2H), 7.25 – 7.17 (m, 1 H), 5.22 (s, 1 H), 4.44 – 4.33 (m, 2H), 4.1 1 – 3.99 (m, 1 H), 3.94 – 3.73 (m, 2H), 3.68 – 3.60 (m, 1 H), 3.1 1 – 3.05 (m, 6H), 3.02 – 2.86 (m, 2H), 2.45 – 2.42 (m, 3H), 2.22 – 1 .97 (m, 2H).

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, 31058-83-0, 6-Chloro-N,N-dimethylpyrimidin-4-amine.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BRANSTETTER, Bryan, James; LETAVIC, Michael, A.; LY, Kiev, S.; RUDOLPH, Dale, A.; SAVALL, Brad, M.; SHAH, Chandravadan, R.; SHIREMAN, Brock, T.; WO2011/50202; (2011); A1;,
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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.105806-13-1, name is 4,6-Dichloro-5-fluoro-2-methylpyrimidine, molecular formula is C5H3Cl2FN2, molecular weight is 181, as common compound, the synthetic route is as follows.COA of Formula: C5H3Cl2FN2

[00343] To a mixture of 4,6-dichloro-5-fluoro-2-methyl-pyrimidine (390 mg, 2.15 mmol) and diisopropylethylamine (900 mu, 5.17 mmol) in dichloromethane (3.9 mL) was added l-(oxetan-3-yl)piperazine (335 mg, 2.4 mmol) . The mixture was stirred for 10 minutes. The resulting mixture was concentrated in vacuo then purified on a 40 g silica gel cartridge eluting with 0-80% ethyl acetate/heptane to provide 4-chloro- 5-fluoro-2-methyl-6-[4-(oxetan-3-yl)piperazin-l-yl]pyrirnidine (550 mg, 89%). XH NMR (400 MHz, CDC13) delta 5.35 (s, 1H), 4.92 – 4.70 (m, 2H), 4.65 – 4.41 (m, 2H), 4.68 – 4.12 (m, 2H), 2.46 (d, J = 1.1 Hz, 3H), 1.79 (d, J = 0.7 Hz, 3H) ppm. ESI-MS m/z calc. 231.05746, found 232.0 (M+l) +; Retention time: 0.65 minutes.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,105806-13-1, 4,6-Dichloro-5-fluoro-2-methylpyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; COLLIER, Philip, N.; DAVIES, Robert, J.; DENINNO, Michael, Paul; DOYLE, Elisabeth; FRANTZ, James, Daniel; GOLDMAN, Brian, Anthony; GRILLOT, Anne-Laure; KOLPAK, Adrienne, Lynne; KRAUSS, Raul, Eduardo; LEDFORD, Brian; LIAO, Yusheng; MAGAVI, Sanjay, Shivayogi; MALTAIS, Francois; PEROLA, Emanuele; RYU, Elizabeth, Jin-Sun; SYKEN, Joshua; TANG, Qing; WANG, Tiansheng; (221 pag.)WO2018/106643; (2018); A1;,
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Related Products of 6299-85-0 ,Some common heterocyclic compound, 6299-85-0, molecular formula is C6H4Cl2N2O2, 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.

44Step 1. To a mixture of 256-dichloro-pyrimidine-4-carboxylic acid methyl ester [1 g, 4.83 mmol, Intermediate (54)] and N,N-diisopropylethylamine (1.27 mL, 7.25 mmol) in THF (16 mL) is added 2- (4-methoxyphenyl)-ethylamine (707 ?L, 4.83 mmol). The resulting mixture is stirred at ambient temperature for 20 hours and poured into 50 mL water and extracted three times with 40 mL ethyl acetate. The organic extracts are combined and washed with 20 mL brine, dried over magnesium sulfate, filtered and concentrated to afford a solid which is purified via flash column chromatography on silica gel (35 g) eluting with 5 to 50% EtOAc in heptane gradient to afford 2-chloro-6-|”2-(4- methoxy-phenyl)-ethylamino]-pyrimidine-4-carboxylic acid methyl ester [1 g, 64.5%, Intermediate (55)]. LCMS: Rx = 2.9 minutes, MS: 322 (M+H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,6299-85-0, its application will become more common.

Reference:
Patent; AVENTIS PHARMACEUTICALS INC.; WO2006/44732; (2006); A2;,
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Electric Literature of 90213-67-5, 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. 90213-67-5, name is 2,4-Dichloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine. A new synthetic method of this compound is introduced below.

General procedure: A solution of compound 1 (0.3 mmol) in anhydrous toluene (2 mL)was flushed with Ar, after which Pd(PPh3)2Cl2 (10.5 mg, 0.015 mmol),AsPh3 (18.4 mg, 0.06 mmol) and the corresponding (arylethynyl)tributyltin (0.78 mmol) were added. The mixture was heated at reflux temperature under Ar for 48-72 h. After cooling, the mixture was poured into K2CO3 solution (0.5 M, 20 mL) containing CsF (50mg), stirred for 30 min and extracted with CHCl3. The extract was dried over Na2SO4, filtered and the CHCl3 was removed on a rotary evaporator. The crude residue was purified by column chromatography(CHCl3) to afford pure product 6q-y.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,90213-67-5, 2,4-Dichloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Article; Bucevicius, Jonas; Tumkevicius, Sigitas; Synthesis; vol. 47; 14; (2015); p. 2100 – 2112;,
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Related Products of 3764-01-0, 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 3764-01-0 as follows.

2,4,6-Trichloropyrimidine (5.5 mL, 48.0 mmol) was dissolved in tetrahydrofuran (70 mL).Then, palladium acetate (0.147 g, 0.64 mmol) was sequentially added thereto.Triphenylphosphine (353 mg, 1.28 mmol),p-Methoxybenzeneboronic acid (5.01 g, 31.9 mmol)And aqueous sodium carbonate (1M, 64 mL, 64 mmol),The resulting mixture was heated to 60 C under a nitrogen atmosphere and stirred for 6 hours.Cool to room temperature, concentrate under reduced pressure to remove organic solvent.Water (100 mL) was added to the residue.The resulting mixture was extracted with ethyl acetate (100 mL¡Á3).The combined organic phases were washed with brine (100 mL).Dry anhydrous sodium sulfate, filter, and concentrate the filtrate to dryness.The residue was purified by EtOAc EtOAc EtOAc(5.58g, 68%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3764-01-0, its application will become more common.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Ren Qingyun; Tang Changhua; Yin Junjun; Yi Kai; Lei Yibo; Wang Yejun; Zhang Yingjun; (138 pag.)CN108276401; (2018); A;,
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Electric Literature of 10457-14-4, 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.10457-14-4, name is 2,4-Bis((trimethylsilyl)oxy)pyrimidine, molecular formula is C10H20N2O2Si2, molecular weight is 256.449, as common compound, the synthetic route is as follows.

To a solution of Compound 39 (927 mg, 2.00 mmol) in dry CH2CI2 (5 mL) was added HBr (1.16 mL, 4.28 mmol, 33% in AcOH) under N2. And the resultant mixture was stirred under N2 for 17 h. The reaction mixture was washed with twice H2O and NaHCC>3, dried (MgSC^) and concentrated under reduced pressure to give the crude bromide (838 mg) as a pale yellow oil. In a separate flask, uracil (269 mg, 2.40 mmol) and (NH4)2S04 (16 mg) in hexamethyldisilazane (5.0 mL) was heated to reflux under N2 for 22 h. The reaction mixture was concentrated under reduced pressure and dried under high vacuum to give the crude bis-TMS-uracil as a colorless oil. The crude bromide in dry CHCI3 (10 mL) was added to crude bis-TMS-uracil via cannula under N2. The resultant mixture was heated to reflux under N2 for 18 h and then quenched with H2O and stirred at RT for 30 min. The phases were separated and the aqueous phase was extracted twice with CH2CI2. The combined organic extracts were dried (MgS04) and concentrated under reduced pressure. Recrystalhzation from EtOH gave Compound 40 (598 mg) as a colorless solid.

Statistics shows that 10457-14-4 is playing an increasingly important role. we look forward to future research findings about 2,4-Bis((trimethylsilyl)oxy)pyrimidine.

Reference:
Patent; NOVADEX PHARMACEUTICALS AB; ZHOU, Xiao Xiong; TORSSELL, Staffan; WALLNER, Olov; SUN, Piaoyang; WO2011/75052; (2011); A1;,
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