Pyrimidines

Adding a certain compound to certain chemical reactions, such as: 69034-12-4, 2-Chloro-5-(trifluoromethyl)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, 69034-12-4, blongs to pyrimidines compound. category: pyrimidines

To a solution of ingenol (145 mg, 0.416 mmol) and 2-chloro-5- (trifluoromethyl)pyrimidine (76 mg, 0.416 mmol) in DMF ( 3 ml_) at RT was added triethylamine (0.1 16 ml_, 0.832 mmol). After 39.5 hours, the mixture was purified by C18 using an ISCO instrument [20-60% ACN gradient over 25 min, 30 g ISCO gold column] to give impure product which was further purified by silica gel chromatography [10-75% EtOAc in hexanes, 12 g ISCO column]. The fractions were concentrated and lyophilized from ACN/water to give (1 aR,2S,5R,5aR,6S,8aS,9R,10aR)-5,5a,6-trihydroxy-1 ,1 ,7,9-tetramethyl- 4-(((5-(trifluoromethyl)pyrimidin-2-yl)oxy)methyl)-1 a,2,5,5a,6,9,10,10a-octahydro-1 H-2,8a- methanocyclopenta[a]cyclopropa[e][10]annulen-1 1 -one (10.8 mg, 0.021 mmol, 5% yield). 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 0.65 – 0.76 (m, 1 H), 0.93 – 1 .02 (m, 4 H), 1 .06 (s, 3 H), 1 .13 (s, 3 H), 1 .73 – 1 .83 (m, 1 H), 1 .87 (s, 3 H), 2.22 – 2.39 (m, 2 H), 2.44 (d, J=5.1 Hz, 1 H), 2.97 (d, J=10.8 Hz, 1 H), 3.87 (d, J=10.3 Hz, 1 H), 4.10 (s, 1 H), 4.16 (d, J=1 1 .5 Hz, 1 H), 4.47 (d, J=6.0 Hz, 1 H), 4.91 (d, J=12.3 Hz, 1 H), 5.08 (d, J=12.1 Hz, 1 H), 5.96 (s, 1 H), 6.28 (d, J=4.0 Hz, 1 H), 8.75 (s, 2 H); LCMS(ESI) m/z: 495.3 (M+1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,69034-12-4, its application will become more common.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; TAI, Vincent Wing-Fai; TANG, Jun; (98 pag.)WO2017/130156; (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. 17321-93-6, name is 2-Amino-5-bromo-4-methylpyrimidine, the common compound, a new synthetic route is introduced below. Application In Synthesis of 2-Amino-5-bromo-4-methylpyrimidine

Intermediate G 4-Methyl-5-(4,4,5,5-tetramethyl-[l,3,2]dioxoborolan-2-yl]-pyrimidin-2-ylamine; Palladium II dichloride (0.189 g, 1.06 mmol) is added to a solution of [1,1- bis(diphenylphosphino)ferrocene] (0.608 g, 1.06 mmol) in degassed dimethylformamide (20 ml) and the mixture is stirred at 50° C for 15 min. After cooling to room temperature 5-bromo-4-methylpyrimidine-2-ylamine (1.0 g, 5.32 mmol), bis-(4,4,5,5-tetramethyl- [l,3]dioxolan-2-yl]-borane (1.65 g, 6.38 mmol) and potassium acetate (1.57 g , 16 mmol) are added. The mixture is heated at 95° C for 16 hours then the solvent is removed under reduced pressure. The crude mixture is suspended in DCM (250 ml) and filtered through a pad of Celite.(R). (filter agent), the filtrate was washed with water (20 ml), dried over MgSO4 and evaporated to dryness. Purification by flash chromatography on silica using cyclohexane/ ethyl acetate (4 : 1) mixture provides the title compound.

The synthetic route of 17321-93-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; WO2009/13348; (2009); A2;,
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Related Products of 137281-39-1, 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.137281-39-1, name is 4-(2-(2-Amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl)benzoic acid, molecular formula is C15H14N4O3, molecular weight is 298.3, as common compound, the synthetic route is as follows.

General procedure: To a suspension of compound 6 (0.033 mmol) in N,N-dimethylformamide (5 mL), corresponding amine (RNH2) (0.033 mmol) and DIPEA (0.1 mmol) were added at about 10 C under nitrogen atmosphere. To this, diethylphosphorocyanidate(0.04 mmol) was added slowly over a period of 15 min. The resultant solution was stirred for 3 h at about 10 C. The reaction was complete by TLC (TLC system: 10% methanol in chloroform). Reaction was slowly quenched using saturated sodium-bi-carbonate solution and the resulted solid was stirred for 30min. Solid was collected by filtration and the wet cake was washed with saturated sodium-bi-carbonate solution. Upon drying the wet cake for an hour under vacuum, it was further suspended in methanol and stirred for 30 min, filtered, collected and dried to get respective pure compounds.

Statistics shows that 137281-39-1 is playing an increasingly important role. we look forward to future research findings about 4-(2-(2-Amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl)benzoic acid.

Reference:
Article; Balaraman, Selvakumar; Nayak, Nagaraj; Subbiah, Madhuri; Elango, Kuppanagounder P.; Medicinal Chemistry Research; vol. 27; 11-12; (2018); p. 2538 – 2546;,
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Adding a certain compound to certain chemical reactions, such as: 116247-92-8, 1-Pyrimidin-2-yl-piperidin-4-one, 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 C9H11N3O, blongs to pyrimidines compound. Computed Properties of C9H11N3O

B. (4-Bromo-2-methyl-phenyl)-( 1 -pyrimidin-2-yl-piperidin-4-yl)-amine : To the mixture of 4-bromo-2-methylaniline (285 mg, 1.5 mmol) and l-pyrimidin-2-yl-piperidin- 4-one (266 mg, 1.5 mmol) in MeOH/AcOH (10:1, 5 ml) was added BH3-Py in THF (8M, 188 mul). The mixture was stirred at rt for 2h. The reaction mixture was concentrated and to the residue was added HCl (10%, 10 ml). The resulting mixture was stirred at room temperature for 30 min., then with cooling, the mixture was adjusted to alkaline with solid Na2CO3 and water. The aqueous layer was extracted with EtOAc (5 x 30 ml). The EPO EtOAc was dried (Na2SO4) and concentrated. The residue was subjected to ISCO to give the titled compound as a white solid (140 mg). HPLC: column, Luna Phenyl-Hexyl 5 mum 4.6×50 mm, 10-90% solvent B (acetonitrile) in solvent A (IO mM ammonium acetate aq) over 3 min., flow rate 3 ml/min, retention time, 2.71 min.; MS (MH+: 347 and 349). 1H NMR (400 MHz, chloroform- d), delta ppm 1.46 (ddd, J=24.30, 10.86, 4.04 Hz, 2H), 2.10 (s, 3 H), 2.17 (dd, J=13.14, 2.78 Hz, 2 H), 3.20 (ddd, J=14.00, 11.87, 2.78 Hz, 1 H), 3.40 (br. s., 1 H), 3.60 (br. s., 1 H), 4.68 (ddd, J=13.52, 3.41, 3.28 Hz, 2 H), 6.50 (t, J=4.67 Hz, 1 H), 6.57 (d, J=8.59 Hz, 1 H), 7.19 (s, 1 H), 7.23 (dd, J=8.59, 2.27 Hz, 1 H), 8.33 (d, J=4.80 Hz, 2 H).; B. (4-Bromo-2-methyl-phenyl)-( 1 -pyrimidin^-yl-piperidin^-yl)- amine : To the mixture of bromoaniline (285 mg, 1.5 mmol) and ketone (266 mg, 1.5 mmol) in MeOH/AcOH (10:1, 5 ml) was added BH3-Py in THF (8M, 188 mul). The mixture was stirred at rt for 2h. The reaction mixture was concentrated and to the residue was added HCl (10%, 10 ml). The resulting mixture was stirred at rt for 30 min., then with cooling, EPO the mixture was adjusted to alkaline with solid Na2CO3 and water. The aq. layer was extracted with EtOAc (5x 30 ml). The EtOAc was dried (Na2SO4) and concentrated. The residue was subjected to ISCO to give the titled compound as a white solid (140 mg).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,116247-92-8, 1-Pyrimidin-2-yl-piperidin-4-one, and friends who are interested can also refer to it.

Reference:
Patent; LEXICON PHARMACEUTICALS, INC.; WO2008/58064; (2008); A1;,
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Reference of 1192479-35-8, 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 1192479-35-8, name is 2-Chloro-5-fluoro-4-methoxy-6-methylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

A 1 :3 mixture of 4-(bromomethyl)-2-chloro-5-fluoro-6-methoxypyrimidine : 2- chloro-5-fluoro-4-methoxy-6-methylpyrimidine (2.61 g) was dissolved in dry acetonitrile (10 ml) and sodium acetate (0.3 g) added. The reaction mixture was heated at 90C for seventeen hours then the reaction mixture was cooled and poured into cold water and extracted with dichloromethane (100 ml). The organic layer was dried (MgSC”4) and evaporated and the residue was purified by silica gel column chromatography (gradient from 0 to 10% ethyl acetate / hexane) to afford the title compound (0.455 g) as an oil. LCMS: Rt 1.34 min, m/z 235 [M+H]+.

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 1192479-35-8, 2-Chloro-5-fluoro-4-methoxy-6-methylpyrimidine.

Reference:
Patent; EISAI R&D MANAGEMENT CO., LTD.; HALL, Adrian; FARTHING, Christopher Neil; EATHERTON, Andrew John; WO2014/13076; (2014); A1;,
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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. 479691-42-4, name is tert-Butyl 4-(4-chloropyrimidin-2-yl)piperazine-1-carboxylate. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C13H19ClN4O2

A mixture of tert-butyl 4-(2-chloropyrimidin-4-yl)piperazine-1-carboxylate (9.00g, 30.1mmol), (2,3-difluorophenyl)boronic acid (7.10g, 45.1mmol), 1M aq Na2CO3 (41 mL, 82.0 mmol), tetrakis(triphenylphosphine)palladium (0) (4.2g, 3.61 mmol), and DME (270 mL) was stirred at 95 C overnight under N2 atmosphere. After cooling to room temperature, the mixture was diluted with water, and extracted with EtOAc. The organic layer was washed with water, dried over anhydrous MgSO4, and concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane-EtOAc) to give 12 (11.3g, quant.) as pale yellow crystals.

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, 479691-42-4, tert-Butyl 4-(4-chloropyrimidin-2-yl)piperazine-1-carboxylate.

Reference:
Article; Kono, Mitsunori; Matsumoto, Takahiro; Imaeda, Toshihiro; Kawamura, Toru; Fujimoto, Shinji; Kosugi, Yohei; Odani, Tomoyuki; Shimizu, Yuji; Matsui, Hideki; Shimojo, Masato; Kori, Masakuni; Bioorganic and Medicinal Chemistry; vol. 22; 4; (2014); p. 1468 – 1478;,
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Related Products of 7627-44-3, Adding some certain compound to certain chemical reactions, such as: 7627-44-3, name is 2,4-Dichloro-5-(iodomethyl)pyrimidine,molecular formula is C5H3Cl2IN2, 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 7627-44-3.

A mixture of 2,4-dichloro-5-(iodomethyl)pyrimidine (1.50 g, 5.19 mmol), 2,6- difluoro-3,5-dimethoxyaniline (1.08 g, 5.71 mmol) in N,N-diisopropylethylamine (4 mL) was stirred at 80 °C for 2 hours. After being cooled to room temperature, the reaction mixture was concentrated under reduced pressure. The residue was purified on silica gel (eluting with 0- 40percent EtOAc in DCM) to give 1.70 g of the desired product. LCMS calculated for C13H12CI2F2N3O2 [M+H]+ m/z: 350.0; Found: 350.0.

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. 7627-44-3, 2,4-Dichloro-5-(iodomethyl)pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; INCYTE CORPORATION; LU, Liang; WU, Liangxing; QIAN, Ding-Quan; YAO, Wenqing; (102 pag.)WO2016/134314; (2016); A1;,
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Synthetic Route of 428854-24-4, 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.428854-24-4, name is 2-(1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl)pyrimidine-4,5,6-triamine, molecular formula is C17H15FN8, molecular weight is 350.35, as common compound, the synthetic route is as follows.

Step three, A solution of formic acid (129 g, 1.37 mol)Was added dropwise to acetic anhydride (145 g, 1.42 mol)After stirring for half an hour, compound 4 (80 g, 0.23mo 1) was added at 0 C, stirred at 20 C for 10 hours,TLC detection reaction is completed, concentrated reaction solution, add 500mL of water for half an hour, pumping,Dried to give about 78 g of a yellow solid which was dissolved in 500 mL of tetrahydrofiramidate and sodium borohydride (15.58 g, 0.41 mol) was added at room temperature. A solution of boron trifluoride diethyl ether (90 mL) was slowly added dropwise at room temperature, Slowly heated to reflux for 3 hours. After the reaction, add 120mL methanol to destroy, then add 2N hydrochloric acid 120mL, stir for half an hour after the reaction system, the residue with 2N sodium hydroxide solution to adjust the pH to neutral, and then suction, Drying to obtain a crude product of compound 5a,The crude product of compound 5a was dissolved in a mixed solvent of dichloromethane and methanol (the weight ratio of the crude product of compound 5a to 1: 5, the volume ratio of dichloromethane to methanol in the mixed solvent was 1: 15) ,And the mixture was stirred at room temperature for 10 hours and then filtered and dried to obtain pure product (63.7 g, 0.17 mol, yield: 76%, content: 99%) /

The chemical industry reduces the impact on the environment during synthesis 428854-24-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Anhui Lianchuang Biological Medicine Co.,Ltd; GE, DEPEI; WU, QIHUA; LIU, TAO; (10 pag.)CN104530044; (2016); B;,
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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.39551-54-7, name is 2,4-Dichloropyrido[3,2-d]pyrimidine, molecular formula is C7H3Cl2N3, molecular weight is 200.0248, as common compound, the synthetic route is as follows.Application In Synthesis of 2,4-Dichloropyrido[3,2-d]pyrimidine

2,4,-dichloropyrido[3,2-d]pyrimidine (33 mg, 0.16 mmol, 1.25 equiv.) was treated with THF (10 mL) followed by N,N-diisopropylethylamine (0.18 mL, 1.0 mmol, 8 equiv.), and (R)-methyl 2-amino-5,5-difluorohexanoate 78C (36 mg, 0.13 mmol, 1 equiv., TFA salt). The reaction mixture was stirred for 1 h to generate 78D and then this mixture was used directly. LCMS (m/z): 345.13 [M+H]+; tR=1.08 min. on LC/MS Method A.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,39551-54-7, 2,4-Dichloropyrido[3,2-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Gilead Sciences, Inc.; Aktoudianakis, Evangelos; Chin, Gregory; Mackman, Richard L.; Metobo, Samuel E.; Mish, Michael R.; Pyun, Hyung-jung; Zablocki, Jeff; (175 pag.)US2016/289229; (2016); A1;,
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Adding a certain compound to certain chemical reactions, such as: 43212-41-5, 2,4-Dichloro-6-methoxypyrimidine, 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, 43212-41-5, blongs to pyrimidines compound. name: 2,4-Dichloro-6-methoxypyrimidine

Example I.3 2,4-Dichloro-6-trichloromethoxypyrimidine 303 g (4.27 mol) of chlorine were passed into a mixture of 209 g (1.168 mol) of 2,6-dichloro-4-methoxypyrimidine and 2 g (0.012 mol) of alpha,alpha’-azoisobutyronitrile while stirring at 80 C. for hour, at 100 C. for hour, at 120 C. for 3 hours and at 150 C. for 3 hours and subjecting to UV irradiation, with monitoring of the progress of the reaction by gas chromatography. The reaction mixture was then distilled under reduced pressure. 241.3 g (73% of theory) of the title compound of boiling point 87-88 C./0.4 mbar, melting point 55-56 C. were obtained.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,43212-41-5, its application will become more common.

Reference:
Patent; BASF Aktiengesellschaft; US5237063; (1993); A;,
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Pyrimidine – Wikipedia