Pyrimidines

Adding a certain compound to certain chemical reactions, such as: 698-29-3, 4-Amino-2-methylpyrimidine-5-carbonitrile, 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, category: pyrimidines, blongs to pyrimidines compound. category: pyrimidines

Method A 6-(2,6-Dichlorophenyl)-2-methylpyrido[2,3,-d]-pyrimidin-7-amine A mixture of 76.5 g of 4-amino-2-methylpyrimidine-5-carbonitrile, 380 ml of 97% formic acid, 380 ml of water, and 8 g of Raney nickel catalyst is treated in a Parr pressure apparatus with hydrogen gas at an initial pressure of 51 psi at room temperature for 2.75 hours. The catalyst is removed by filtration and the filtrate is treated with 47.5 ml of concentrated hydrochloric acid and evaporated at reduced pressure. The residue is dissolved in hot water, treated with charcoal and filtered. Neutralization of the filtrate with concentrated ammonium hydroxide precipitates the product which is then collected by filtration and washed with water. Recrystallization from ethanol gives 37.9 g of 4-amino-2-methylpyrimidine-5-carboxaldehyde, mp 191-192.5 C.

The synthetic route of 698-29-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Warner-Lambert Company; US4271164; (1981); A;,
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Electric Literature of 18740-39-1, 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 18740-39-1, name is 2,4-Dichlorothieno[2,3-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Pd(PPh3)2Cl2 (23 mg, 0.03 mmol), 4-trifluoromethoxyphenylboronic acid (73 mg, 0.35 mmol), compound 15 (100 mg, 0.32 mmol) and TEA (91 mg, 0.90 mmol) were added to a solution of DMF (5 mL) and H2O (0.5 mL). The mixture was stirred at 80 oC for 4 h. Water (10 mL) and EtOAc (30 mL) were added to the reaction. The layers were separated. The aqueous layer was extracted using EtOAc (10 mL). The combined organic extracts were dried over anhydrous Na2SO4. The solvent was removed under reduced pressure, and the resulting residue was purified via silica gel column chromatography using petroleum ether/EtOAc (5/1) to give 16 (67 mg, 48 percent) as a yellow solid.

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 18740-39-1, 2,4-Dichlorothieno[2,3-d]pyrimidine.

Reference:
Article; Zhang, Liandi; Xin, Minhang; Shen, Han; Wen, Jun; Tang, Feng; Tu, Chongxing; Zhao, Xinge; Wei, Ping; Bioorganic and Medicinal Chemistry Letters; vol. 24; 15; (2014); p. 3486 – 3492;,
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Electric Literature of 5399-92-8, 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. 5399-92-8, name is 4-Chloro-1H-pyrazolo[3,4-d]pyrimidine, molecular formula is C5H3ClN4, 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.

To a stirred solution of 4-chloro-1H-pyrazolo[3,4-d]pyrimidine (2.5 g, 16.23 mmol, 1 equiv) in DCM (30 mL) was added NBS (3.4 g, 19.48 mmol, 1.2 equiv) at 000. The reaction mixture was warmed to room temperature and stirred for 0/N. The reaction mixture was quenched with water and extracted with ethyl acetate. The organic layer was dried over sodium sulphate evaporated to obtain crude which was purified over silica gel flash column chromatography. The compound eluted out in 15% ethyl acetate in n-hexane to afford 3-bromo-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one (1.3 g, crude) as pale yellow solid. 1H NMR (400 MHz, DMSO-d6) O ppm – 8.02 (s, 1H), 12.18 (s, 1H), 14.00 (br.s, 1H)

According to the analysis of related databases, 5399-92-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; AXTEN, Jeffrey Michael; FAUCHER, Nicolas Eric; DAUGAN, Alain Claude-Marie; (110 pag.)WO2017/46738; (2017); A1;,
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Reference of 374930-88-8, 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 374930-88-8, name is tert-Butyl 4-(5-bromopyrimidin-2-yl)piperazine-1-carboxylate. This compound has unique chemical properties. The synthetic route is as follows.

Step 1: Synthesis of tert-butyl 4-(5-(cyclopropylethynyl)pyrimidin-2-yl)piperazine-1-carboxylate In a sealed tube, the mixture of tert-butyl 4-(5-bromopyrimidin-2-yl)piperazine-1-carboxylate (1.0 g, 2.9 mmol), ethynylcyclopropane (482 mg, 7.3 mmol), tetrakis(triphenyl-phosphine)palladium (335 mg, 0.29 mmol) and copper(I) iodide (28 mg, 0.15 mmol) in diethylamine (10 mL) and dimethyl sulfoxide (10 mL) was stirred at 100 C. for 3 hours under nitrogen atmosphere. The mixture was then diluted with ethyl acetate (100 mL) and washed with water and brine. The organic phase was dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography eluting with petroleum ether:ethyl acetate=15:1 to afford tert-butyl 4-(5-(cyclopropylethynyl)pyrimidin-2-yl)piperazine-1-carboxylate (930 mg, 98%) as a yellow solid. MS (ES+) C18H24N4O2 requires: 328, found: 329 [M+H]+.

According to the analysis of related databases, 374930-88-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BLUEPRINT MEDICINES CORPORATION; Hodous, Brian L.; Kim, Joseph L.; Miduturu, Chandrasekhar V.; Wilson, Douglas; Zhang, Yulian; US2015/111857; (2015); 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. 139756-21-1, name is 5-(2-Ethoxyphenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 5-(2-Ethoxyphenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one

PREPARATION 17 5-(2-Ethoxy-5-nitrophenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]-pyrimidin-7-one Concentrated nitric acid (0.5 ml) was added dropwise to a stirred solution of 5-(2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]-pyrimidin-7-one (2.0 g, 0.0064 mol) in concentrated sulphuric acid (10 ml) at 0 C., an the resulting orange solution was stirred at room temperature for 18 hours. The reaction solution was then added dropwise to stirred ice and water (200 g) and the solid precipitate collected by filtration. This solid was then dissolved in dichloromethane (50 ml) and the solution washed successively with brine (2*30 ml) and water (30 ml), dried (Na2 SO4) and evaporated under vacuum to give a yellow solid. Crystallisation from acetronitrile gave the title compound as yellow needles (1.40 g, 61%), m.p. 214-216 C. Found: C,57.36; H,5.21; N,19.49. C17 H19 N5 O4 requires C,57.13; H,5.36; N,19.60%.

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, 139756-21-1, 5-(2-Ethoxyphenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one.

Reference:
Patent; Pfizer Inc.; US5272147; (1993); A;,
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Related Products of 16019-31-1, 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 16019-31-1 as follows.

A solution of compound 4 (100 g, 0.53 mol) in MeOH (400 ml) and CH2Cl2 (150 ml) was cooled to -40C, and ozone was bubbled through the mixture for 2 h. Then the reaction mixture was purged with nitrogen for 20 min to remove the excessive ozone. Thiocarbamide (40 g, 0.53 mol) was added to the mixture and stirred for 1 h until the starch-KI paper did not turn blue. The solvent was distilled off, the residue was extracted with CH2Cl2 (300 ml) and washed with water (2×100 ml). The organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure to give the residue that was triturated with petroleum ether (200 ml). Yield 76.8 g (76%), white solid, mp 88-90C (mp 89-91C19). 1H NMR spectrum (DMSO-d6), delta, ppm: 9.75 (1H, s, CHO); 8.89 (1H, s, H-2); 4.24 (2H, s, CH2).13C NMR spectrum (DMSO-d6), delta, ppm: 196.9; 161.8;157.0; 126.4; 44.5. Mass spectrum, m/z (Irel, %): 192[M(35Cl,37Cl)]+(12), 190 [M(35Cl)]+ (20), 162 (100).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,16019-31-1, its application will become more common.

Reference:
Article; Zhang, Yu-Liu; Xu, Cheng-Tao; Liu, Ting; Zhu, Yong; Luo, Yu; Chemistry of Heterocyclic Compounds; vol. 54; 6; (2018); p. 638 – 642; Khim. Geterotsikl. Soedin.; vol. 54; 6; (2018); p. 638 – 642,5;,
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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. 51421-99-9, name is 4-Chloro-2-methoxypyrimidine, molecular formula is C5H5ClN2O, 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. Application In Synthesis of 4-Chloro-2-methoxypyrimidine

INTERMEDIATE 62 4-(“3-Bromo-4-fluoro-lH”-pyrazol-l-vn-2-methoxypyrimidine To a solution of 3-bromo-4-fluoro-lH-pyrazole (500 mg, 3.03 mmol) in anhydrous DMSO (6 mL) was added NaH (133 mg, 3.13 mmol) at 0C. The mixture was stirred for 30 min at 0 C, followed by the addition of 4-chloro-2-methoxypyrimidine (438 mg, 3.03 mmol) in DMSO (2 mL). The resulting mixture was stirred at 90 C overnight. The mixture was cooled to room temperature, quenched with water (10 mL) and extracted with EtOAc (40 mL x 3). The organic layer was collected and dried over Na2S04. The solvent was removed in vacuo to give the crude product. This was purified by flash chromatography (ISCO Combiflash, 24g, Biotage Si column, ~60 mL/min, 100% hexanes 5 min, gradient to 100% EtOAc in hexanes 15 min) to afford 4-(3-bromo-4-fluoro-lH-pyrazol-l-yl)-2-methoxypyrimidine. LCMS calc. = 274.98; found = 274.90 (M+H)+.

With the rapid development of chemical substances, we look forward to future research findings about 51421-99-9.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MOCHIDA PHARMACEUTICAL CO., LTD.; SMITH, Cameron, James; TAN, John, Qiang; ZHANG, Ting; BALKOVEC, James; GREENLEE, William, John; GUO, Liangqin; XU, Jiayi; CHEN, Yi-heng; CHEN, Yili; CHACKALAMANNIL, Samuel; HIRABAYASHI, Tomokazu; NAGASUE, Hiroshi; OGAWA, Kouki; WO2014/120346; (2014); A1;,
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Related Products of 149849-92-3, 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. 149849-92-3, name is 2-Chloropyrimidine-4-carboxylic acid, molecular formula is C5H3ClN2O2, 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.

A mixture of compound IB (309 mg, 1 mmol), 2-chloropyrimidine-4- carboxylic acid (134.5 mg, 1 mmol) cesium carbonate (975 mg, 3 mmol) in 2 ml of DMSO was heated to 60 0C for 6 h. The product was poured into water and precipitated out of solution and was collected by filtration. The crude material was chromatographed (SiO2, 20 % methanol in dichloromethane) to afford 37 as a white powder: LCMS (97 % purity); retention time = 8.70 min, 432.0 [M + H]; 1H NMR (300 MHz, DMSO): 8.60 (IH, d), 8.25 (IH, d), 7.80 (IH, m), 7.60 (IH, d), 7.45 (IH, d), 7.1-7.2 (2H, m), 7.0 (IH, t), 6.75 (IH, d), 5.25 (2H, s), 3.95 (2H, t), 2.85 (2H, t).

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 149849-92-3, 2-Chloropyrimidine-4-carboxylic acid.

Reference:
Patent; GENENTECH, INC.; THE WALTER AND ELIZA HALL INSTITUTE OF MEDICAL RESEARCH; ABBOTT LABORATORIES; BAELL, Jonathon, Bayldon; BUI, Chinh, Thien; COLMAN, Peter; CZABOTAR, Peter; DUDLEY, Danette, A.; FAIRBROTHER, Wayne, J.; FLYGARE, John, A.; LASSENE, Guillaume, Laurent; NDUBAKU, Chudi; NIKOLAKOPOULOS, George; SLEEBS, Brad, Edmund; SMITH, Brian, John; WATSON, Keith, Geoffrey; ELMORE, Steven, W.; HASVOLD, Lisa, A.; PETROS, Andrew, M.; SOUERS, Andrew, J.; TAO, Zhi-Fu; WANG, Le; WANG, Xilu; DESHAYES, Kurt; WO2010/80503; (2010); A1;,
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Reference of 64224-60-8, 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. 64224-60-8, name is 5-Bromo-4-pyrimidinecarboxylic acid. A new synthetic method of this compound is introduced below.

S-bromopyrimidine^-carboxylic acid (prepared according to the procedure described in U.S patent 4,110,450) (1.0 eq, 6.14 g, 30.2 mmol) was suspended in CH2Cl2 (100 ml). Oxalylchloride (1.1 eq, 2.9 ml, 33.0 mmol) was added followed by 2 drops of DMF. The mixture was stirred at room temperature overnight and the volatiles were removed in vacuo. The residue was taken in MeOH (50 ml) and heated. After evaporation of MeOH in vacuo the compound was dissolved in CH2Cl2 and poured on a prepacked silica gel column. The material was eluted using 20% Ethyl acetate in hexanes. Evaporation of the solvent provided methyl-5- bromopyrimidine-4-carboxylate as a light orange crystalline solid (2.54 g, 39% yield). LCMS (ES): 95% pure, m/z 217 [M]+; 219 [M+2]+; 1H NMR (CDCl3, 400 MHz) delta 4.04 (s, 3H), 9.02 (s, IH), 9.21 (s, IH) ppm.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,64224-60-8, 5-Bromo-4-pyrimidinecarboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; CYLENE PHARMACEUTICALS, INC.; WO2008/28168; (2008); A2;,
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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. 945950-37-8, name is 4-Methyl-7H-pyrrolo[2,3-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C7H7N3

Sten 6: To a stirred solution of (3R,3aS,6aR)-6.-((3-bromo-2-((4-methoxvbenzvl)amino)quinoiin-7-vi)nelhyi)hexahydro-211.-cyciopenta[h]furan-2,3,3a.-trioi (250 rng, 0.486 mmoi) in dry MeCN(9 rnL) was added tributviphosphine (176 ing, 0.869 rnmoi), followed by (E)-diazene-J.2-divlhis(piperi din-i -ylmethanone) (206 111g. 0815 mrnoi) at room temperature. The reactionmixture was stirred at room temperature for I h. and the solution was used directly in the nextstep without characterization; Step 7: To a stirred solution of 4-methyF-7I-Ipyrro1o [2, 3dj pyrimidine (129 mg, 0.970 mniol) in dry DMF (6 mL) was added sodium hydride (60% dispersion in mineral oil) (58.2 111g. 1.46 mmoi) at 0 C. The suspension was stirred at room temperature for 30 minutes, The suspensionwas transferred to the solution from the previous step containing the epoxide intermediate via syringe, and the resulting mixture was stirred at room temperature for 2 h. The reaction mixture was quenched with saturated aqueous ammonium chloride (30 mL) and extracted with EtOAc (40 mL 3). The combined organic layers were washed with brine (40 mL), dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure.The residue was purified by Preparative TLC (MeOH/DCM) to afford (2R,3R,3aS,6aR)-6-(3- bromo-2(rnethoxyhenzyi)amino)quinolin-7-yl)methvi)-2-?4-methyi7H-pyrroio[2,3- d]pyrirnidinT-yi)hexahydro-3aWcyclopenta[hfuran-3, 3a-diol. MS: 630/632 (M+ 1/M+3). ?H NMR (40() M1-lz, DMSO-d6) oe 8.69 (s, 11-1), 8.32 (d, J= 6.0 Hz, IH), 8.02 (s, 1H), 7.54 (d, J= 8.2 Hz, 1H), 7.33 (d, J= 8.4 Hz, 2H), 7.14 -7.04 (rn, 3H), 6.91 -6.80 (m, 4H), 6.03(d, J 8.1Hz, 1H), 5.30 (d, J= 7.0 Hz, 1H), 5.12 (s, 1H), -4.61 (d, J= 6.2 Hz, 2H), 4.22 (t. J 7.6 Hz, 1H),4.04 (d, J == 6.6 Hz. 11-1), 3.72 (s, 31-1), 2.83 (dd, J: 13.7, 7.2 Hz, 11-1), 2.69(s. 31-1). 2.65 (s, 11-1),2,37 -2.22 (m, 11:1), 1.99- 1.93 (mn, 1H). 1,55 (d, J= 6.5 Flz. 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, 945950-37-8, 4-Methyl-7H-pyrrolo[2,3-d]pyrimidine.

Reference:
Patent; MERCK SHARP & DOHME CORP.; IDENIX PHARMACEUTICALS LLC; MACHACEK, Michelle; WITTER, David; GIBEAU, Craig; HUANG, Chunhui; KAWAMURA, Shuhei; SLOMAN, David, L.; SILIPHAIVANH, Phieng; QUIROZ, Ryan; WAN, Murray; SCHNEIDER, Sebastian; YEUNG, Charles, S.; REUTERSHAN, Michael, H.; HENDERSON, Timothy, J.; PAPARIN, Jean-Laurent; RAHALI, Houcine; HUGHES, Jonathan, M., E.; SANYAL, Sulagna; YE, Yingchun; CANDITO, David, A.; FIER, Patrick, S.; SILVERMAN, Steven, M.; (277 pag.)WO2020/33288; (2020); A1;,
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