Pyrimidines

Synthetic Route of 37972-24-0, Adding some certain compound to certain chemical reactions, such as: 37972-24-0, name is 2-Ethynylpyrimidine,molecular formula is C6H4N2, 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 37972-24-0.

To a solution of 229(100mg, 0347mmo1) and 4(723mg, 0.694mmo1) in 2OmL of Et3N was added Pd(PPh3)2C12 (12.18mg, 0Oi7mmoi) and CuT (661mg, 0O35minoi). The mixture wasprotected with N2 atmosphere, then was heated at 70¡ãC for 24 hours. TLC analysis showed complete conversion of starting material to a major product. The reaction mixture was then concentrated in vacuo. The crude product was purified by Prep-HPLC to give the target product Compound 117(18mg, yield: 1962percent).LCNIS: rn/z 265 (M*H)t?H NMR (400 MHz, CDCI3): 5 8.77 (d, J 4.8 Hz, 2H), 7.87 (d, J= 2.4 Hz, 1H), 771-768 (m, 2H, 7.28-7.26 (m, IH), 7.19-7.15 (m, 2H), 679 (d, J= 2.8 Hz, IH).

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. 37972-24-0, 2-Ethynylpyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; HUA MEDICINE (SHANGHAI) LTD.; CHEN, Li; JIN, Xiaowei; (176 pag.)WO2017/117708; (2017); 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. 10070-92-5, name is Pyrimidine-5-carbaldehyde. This compound has unique chemical properties. The synthetic route is as follows. category: pyrimidines

A mixture of pyrimidine-5-carboxaldehyde (2 g, 1 8.50 mmol, 1 .00 equiv) and sodium borohydride (2 g) in MeOH (100 mL) was stirred at 0 – 10C for 30 min. The reaction mixture was concentrated under vacuum and the residue was purified on a silica gel column eluted with DCM/MeOH (50: 1 ) to yield 1 .2 g (59%) of pyrimidin-5-ylmethanol as a light yellow solid. LC/MS (Method K, ESI): RT= 0.74 min, m z = 1 1 1 0 [M+H]+.

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, 10070-92-5, Pyrimidine-5-carbaldehyde.

Reference:
Patent; GENENTECH,INC.; FORMA TM, LLC; BAIR, Kenneth W.; BAUMEISTER, Timm R.; BUCKMELTER, Alexandre J.; CLODFELTER, Kanl H.; DRAGOVICH, Peter; HAN, Bingsong; LIN, Jian; LIU, Xiongcai; REYNOLDS, Dominic J.; SMITH, Chase C.; WANG, Zhongguo; YUEN, Po-Wai; ZAK, Mark; ZHANG, Yamin; ZHENG, Xiaozhang; ZHAO, Guiling; WO2013/127268; (2013); A1;,
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Adding a certain compound to certain chemical reactions, such as: 5399-92-8, 4-Chloro-1H-pyrazolo[3,4-d]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, HPLC of Formula: C5H3ClN4, blongs to pyrimidines compound. HPLC of Formula: C5H3ClN4

EXAMPLE 17; C-M-fiH-Pyrazolobeta^-c/ipyrimidin^-vO-piperidin^-v?-methvlamine To a solution of 4-chloro-1/-/-pyrazolo[3,4-d]pyrimidine (J. Amer. Chem. Soc. 1957, 79, 6407-6413) (51 mg, 0.33 mmol) in ethano] (2 ml) was added triethylamine (100 mul, 0.72 mmol) and 4-(N-Boc-aminomethyl)piperidine (87 mg, 0.41 mmol). The solution was heated at 80 0C for 3 hours, and then cooled to room temperature. The solution was evaporated to dryness and the residue purified by recrystallisation (isopropanol) to yield the intermediate NH-BOC protected product (33 mg, 30% yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,5399-92-8, 4-Chloro-1H-pyrazolo[3,4-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; THE INSTITUTE OF CANCER RESEARCH:ROYAL CANCER HOSPITAL; CANCER RESEARCH TECHNOLOGY LIMITED; WO2007/125315; (2007); A2;,
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Synthetic Route of 3073-77-6, 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 3073-77-6 as follows.

Example 33. (5-Nitro-pyrimidin-2-yl)-[4-(2-pyrrolidin-l-yl-ethoxy)-phenvI1-amine(21); [0169] In a dry 10OmL round bottom flask 5-nitro-pyrimidin-2-ylamine (2 g, 14.3 mmol, 1 equiv), l-[2-(4-bromo-phenoxy)-ethyl]-pyrrolidine (4.45 mL, 21.4 mmol, 1.5 equiv), cesium carbonate (14 g, 42.9 mmol, 3 equiv), 4,5-bis(diphenylphosphino)-9,9- dimethyl xanthene (1.65 g, 1.43 mmol, 0.2 equiv) and tris(dibenzylideneacetone) dipalladium (1.3 g, 0.714 rmnol, 0.1 equiv) were combined. Reactants were flushed with argon, diluted with dioxane (50 mL) and outfitted with reflux condenser. Reaction was heated to reflux for 18 hours. Reaction was cooled to room temperature and filtered. Silica gel chromatography provided the desired nitro product as a yellow powder (1.5 g,)0/ O).; Example 92. iV2-(4-(2-(PyrroIidm-l-vnethoxy)phenvI)pyrimidine-2.,5-diamine (54); [0262] To a solution of the 2-amino-5-nitropyrimidine (0.54 g, 4 mmol) in anhydrous 1,4-dioxane (20 mL) was added l-[2-(4-bromophenoxy)ethyl]pyrrolidine (1.62 g, 6 mmol), Cs2CO3 (5.2 g, 16 mmol), Pd2(dba)3 (0.36 g, 0.4 mmol), and Xantphos (0.7 g, 1.2 mmol). The suspension was heated under reflux for 2 h under argon. The solid was filtered off and washed with EtOAc. The filtrate was washed with brine (1 x 100 mL) and the aqueous was extracted with EtOAc (3 x 50 mL). Combined organic solution was dried (Na2SO4) and concentrated until 10 mL remain solution before adding hexane (100 mL). The mixture was sonicated for 2 min. The solid was collected by filtration and EPO washed with hexane. The crude material was further purified by flash column (CH2Cl2 :MeOH:NH3.H2O = 100:10:1). The obtained yellow solid was dissolved in MeOH (200 mL) and bubbled with Ar for 2 min. before adding 10% Pd-C. The mixture was hydrogenated for Ih at room temperature. The catalyst was filtered off and washed with MeOH. The filtrate was concentrated in vacuo. The desired product was obtained as a yellow solid (0.48 g, 40%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3073-77-6, its application will become more common.

Reference:
Patent; TARGEGEN, INC.; WO2006/101977; (2006); A2;,
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Pyrimidine – Wikipedia

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. 2927-71-1, name is 2,4-Dichloro-5-fluoropyrimidine. A new synthetic method of this compound is introduced below., Recommanded Product: 2927-71-1

A mixture of 2,4-dichloro-5-fluoropyrimidine (10.0 g, 0.06 mol), o-phenylenediamine (7.1 g, 0.066 mol) and DIPEA (20.8 mL, 0.12 mol) in n-butanol (80 mL) was stirred at 110 C. for 16 h then concentrated in vacuo and slurried with 0.1 M hydrochloric acid (20 mL). The solid was collected at the pump, washed with water (2¡Á20 mL), n-butanol (30 mL and diethyl ether (2¡Á30 mL), then dried under vacuum to afford N1-(2-chloro-5-fluoropyrimidin-4-yl)benzene-1,2-diamine as a colourless powder (10.8 g, 71%). 1H NMR (d6-DMSO) delta9.31 (br s, 1H), 8.18 (d, 1H), 6.99-7.03 (m, 2H), 6.74-6.76 (m, 1H), 6.54-6.58 (m, 1H), 5.04 (br s, 2H); LCMS method A, (ES+) 239, 241, RT=1.90 min.

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, 2927-71-1, 2,4-Dichloro-5-fluoropyrimidine.

Reference:
Patent; Harrison, Richard John; Hobson, Andrew; Ramsden, Nigel; US2012/172385; (2012); A1;,
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Adding a certain compound to certain chemical reactions, such as: 55583-59-0, 2,5-Diamino-4,6-dichloropyrimidine, 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, 55583-59-0, blongs to pyrimidines compound. name: 2,5-Diamino-4,6-dichloropyrimidine

To (1 S,4H)-4-amino-2-cyclopentene-1 -methanol tartrate salt (1 g, 4 mmol) in n- BuOH (10 mL) was added 2,5-diamino-4,6-dichloropyrimidine (DADCP, 0.69 g, 4 mmol) and NaHCOs (1 .12 g, 13 mmol) and the mixture was allowed to stir for 16 hr at 95 C. The mixture was cooled and filtered under vacuum. The resulting solvent from the filtrate was removed in vacuo. The crude product was purified by column chromatography (1 :49 to 1 :24 MeOH-DCM) to yield the title compound (0.52 g, 53%) as a pale brown solid, m.p.: 157-159 C (lit. m.p. 158.5- 160.5 C) (29). 1 H NMR (MeOD): delta 5.87 (ddd, J = 5.5, 2.0, 1 .9 Hz, 1 H), 5.80 (ddd, J = 5.6, 2.0, 2.0 Hz, 1 H), 5.07-5.15 (m, 1 H), 3.47-3.56 (m, 1 H), 3.28 (dt, J = 3.2, 1 .6 Hz, 1 H), 2.79-2.83 (m, 1 H), 2.53 (ddd, J= 13.4, 6.4, 6.4 Hz, 1 H), 1 .36 (ddd, J= 13.4, 6.3, 5.9 Hz, 1 H). 13C NMR (MeOD): delta 158.2, 157.3, 143.2, 135.8, 133.9, 1 14.4, 66.4, 57.8, 57.7, 35.8. m/z (ES+) 256.0955 calculated for CioHi5N5035CI: [M+H]+ 256.0965 and 258.0928 calculated for Ci0Hi5N5O37CI: [M+H]+ 258.0936. IR (cm 1): 3451 (N-H), 3324 (N-H), 3125 (br, O-H), 2931 (C-H), 1570 (C=C aromatic), 1430 (CH2), 690 (C-CI).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,55583-59-0, its application will become more common.

Reference:
Patent; THE UNIVERSITY OF LIVERPOOL; O’NEILL, Paul; BERRY, Neil; (52 pag.)WO2017/21716; (2017); A1;,
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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. 4994-86-9, name is 4-Chloro-2-methylpyrimidine. A new synthetic method of this compound is introduced below., HPLC of Formula: C5H5ClN2

To a stirred solution of 4-chloro-2-methylpyrimidine (81 .1 mg, 631 pmol), and cyclopropyl(4-{[2-{[6-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yI)-1 H-benzimidazol-2-yl]amino}-6-(trifluoromethyl)pyridin-4-yl]methyl}piperazin-1 -yl)methanone (200 mg, 351 pmol) in Dioxane(1.7 mL) and water (340 p1) was added sodium carbonate (111 mg, 1.05 mmol) andPd(dppf)C12 . CHCl (42.9 mg, 52.6 pmol). The mixture was heated to reflux for 19 h.Dichloromethane was added, the mixture was filtered and, the solvent was removed invacuum. Preparative reverse phase HPLC (gradient of water and acetonitrile containing ammonia as additive) gave 20.0mg (10 % yield) of the title compound.LC-MS (Method 2): R = 1.16 mm; MS (ESipos): m/z = 537 [M+H]1H-NMR (400 MHz, CHLOROFORM-d) oe [ppm]: 0.725 (4.36), 0.951 (5.34), 1.261 (1.93), 1.284(6.51), 1.648 (2.11), 2.388 (3.45), 2.793 (3.68), 2.845 (16.00), 3.560 (7.24), 7.582 (2.62), 7.985 (1.62), 8.348 (0.99), 8.675 (3.91), 8.688 (3.75), 11.977 (2.41).

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, 4994-86-9, 4-Chloro-2-methylpyrimidine.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; SCHULZE, Volker; HEINRICH, Tobias; PRINZ, Florian; LEFRANC, Julien; SCHROeDER, Jens; MENGEL, Anne; BONE, Wilhelm; BALINT, Joszef; WENGNER, Antje; EIS, Knut; IRLBACHER, Horst; KOPPITZ, Marcus; BOeMER, Ulf; BADER, Benjamin; BRIEM, Hans; LIENAU, Philip; CHRIST, Clara; STOeCKIGT, Detlef; HILLIG, Roman; (1256 pag.)WO2017/102091; (2017); A1;,
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Adding a certain compound to certain chemical reactions, such as: 63234-80-0, 3-(2-Chloroethyl)-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-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, Formula: C11H15ClN2O, blongs to pyrimidines compound. Formula: C11H15ClN2O

General procedure: A creamy white solid of 3-(2-chloroethyl)- 2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a] pyrimidin-4-one (5) (1.0eq) in N,N-dimethylformamide was taken, pottasium carbonate (3.0 eq) was added to the reaction mixture and then the appropriate aliphatic/ aromatic/heterocyclic amines (1.0 eq) were added and the reaction mixture was heated at 80 ¡ãC for 8h. The progress of the reaction was monitored by TLC. Upon completion, the solvent was removed by water wash and extracted with ethyl acetate. The organic layer was washed with 10percent ammonium chloride solution and finally water wash was given to organic layer and dried with anhydrous sodium sulphate. The solvent was evaporated to get crude product which was purified by column chromatography over silica gel (60-120mesh) using hexane: ethyl acetate(8:2) as an eluent.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,63234-80-0, 3-(2-Chloroethyl)-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one, and friends who are interested can also refer to it.

Reference:
Article; Krishnamurthy, Byregowda; Vinaya, Kambappa; Rakshith, Devraj; Prasanna, Doddakunche Shivaramu; Rangappa, Kanchugarakoppal Subbegowda; Medicinal Chemistry; vol. 9; 2; (2013); p. 240 – 248;,
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Adding a certain compound to certain chemical reactions, such as: 1100318-96-4, 4-Iodo-7H-pyrrolo[2,3-d]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, Safety of 4-Iodo-7H-pyrrolo[2,3-d]pyrimidine, blongs to pyrimidines compound. Safety of 4-Iodo-7H-pyrrolo[2,3-d]pyrimidine

Dry DMFWas added K2CO3 to a solution of 4-iodo-7h-pyrrolo [2,3-d] pyrimidine (4) and the mixture was stirred at room temperature for 30 minutes. After 30 minutes, 2- (trimethylsilyl) ethoxymethyl chloride was added dropwise to the solution,The reaction was stirred for 6 hours. For quenching, a saturated aqueous NH4Cl solution was added to the solution. The mixture was poured into ethyl acetate and extracted twice with ethyl acetate. The combined organic layers were dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel column chromatography (hexane / ethyl acetate) to give the desired compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1100318-96-4, 4-Iodo-7H-pyrrolo[2,3-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Gwangju Institute of Science and Technology; INDUSTRY-ACADEMIC COOPERATION FOUNDATION GYEONGSANG NATIONAL UNIVERSITY; Kim, Yong-Chul; Han, Son-Young; Ko, Hyo-Jin; Lee, Son-Mi; (28 pag.)KR2016/124034; (2016); A;,
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Reference of 59549-51-8, Adding some certain compound to certain chemical reactions, such as: 59549-51-8, name is 5-Bromo-2-chloro-4-(methylthio)pyrimidine,molecular formula is C5H4BrClN2S, 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 59549-51-8.

To a stirring suspension of 5-bromo-2-chloro-4-(methylthio)pyrimidine (1.0 g, 4.18 mmol) in ethanol (6.0 mL) was added 1-methylcyclopropanamine hydrochloride (0.674 g, 6.26 mmol) and DIEA (2.188 mL, 12.53 mmol). The mixture was stirred at 90 C for 16 h. Upon completion of the reaction as indicated by LCMS and TLC the reaction mixture was concentrated and purified by silica gel chromatography using a gradient of 0% – 20% ethyl acetate in hexanes. The product fractions were combined and concentrated to afford 5-bromo-N-(l-methylcyclopropyl)-4- (methylthio)pyrimidin-2-amine (0.665g, 58%> yield) as a white solid. MS (ESI) m/z 276.2[M+l]+.

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. 59549-51-8, 5-Bromo-2-chloro-4-(methylthio)pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SIGNAL PHARMACEUTICALS, LLC; BENNETT, Brydon, L.; ELSNER, Jan; ERDMAN, Paul; HILGRAF, Robert; LEBRUN, Laurie, Ann; MCCARRICK, Meg; MOGHADDAM, Mehran, F.; NAGY, Mark, A.; NORRIS, Stephen; PAISNER, David, A.; SLOSS, Marianne; ROMANOW, William, J.; SATOH, Yoshitaka; TIKHE, Jayashree; YOON, Won, Hyung; DELGADO, Mercedes; WO2012/145569; (2012); A1;,
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