Pyrimidines

Adding a certain compound to certain chemical reactions, such as: 144927-57-1, Ethyl 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate, 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: Ethyl 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate, blongs to pyrimidines compound. Recommanded Product: Ethyl 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate

To ethyl 4-chloro-7H-pyrrolo[2,3-if]pyrimidine-5-carboxylate (10.0 g, 44.3 mmol), (3-nitrophenyl)boronic acid (1 1.8 g, 70.9 mmol), PdCl2(dppf)-CH2Cl2 (3.62 g, 4.43 mmol) and aqueous sodium carbonate (2 M solution, 55.4 mL, 111 mmol) in a flask was added DMF (148 mL). The mixture was degassed for 10 minutes then heated at 1 15 C for 1.5 hours. The reaction was cooled to ambient temperature, then water was added and the mixture was extracted with DCM (*3) and EtOAc (*1). The combined organics were concentrated, diluted with EtOAc (300 mL) and washed with sorbitol/Na2C03 solution to remove excess boronic acid. The aqueous layer was extracted with EtOAc (x4). The combined organics were concentrated after which EtOAc and hexanes were added with stirring. The resulting precipitate was filtered to give solid product that was further triturated with DCM and hexanes to give ethyl 4-(3-nitrophenyl)-7H-pyrrolo[2,3- < ]pyrimidine-5-carboxylate. The combined organic fractions were concentrated under reduced pressure to give a residue containing product and DMF. Addition of MeOH and water led to formation of a precipitate which was filtered to afford additional ethyl 4-(3- nitrophenyl)-7H-pyrrolo[2,3-i ]pyrimidine-5-carboxylate. LRMS (ESI) calc'd for C,5Hi3N404 [M+H]+: 313, found 313. NMR (600 MHz, DMSO-D6) delta 13.17 (s, 1H), 8.99 (s, 1H), 8.43 (s, 1H), 8.39-8.36 (m, 2H), 8.12 (d, J= 7.8 Hz, 1H), 7.79 (t, J= 7.8 Hz, 1H), 3.93 (q, J= 7.2 Hz, 2H), 0.95 (t, J= 7.2 Hz, 3H). The synthetic route of 144927-57-1 has been constantly updated, and we look forward to future research findings. Reference:
Patent; MERCK SHARP & DOHME CORP.; AHEARN, Sean, P.; CHRISTOPHER, Matthew; JUNG, Joon; PU, Qinglin; RIVKIN, Alexey; SCOTT, Mark, E.; WITTER, David, J.; WOO, Hyun Chong; CASH, Brandon; DINSMORE, Christopher; GUERIN, David; WO2013/85802; (2013); A1;,
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Pyrimidine – Wikipedia

Application of 588-36-3 ,Some common heterocyclic compound, 588-36-3, molecular formula is C6H9N3OS, 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.

The mixture of intermediate compound 1 (14.6 mmol) and activated MnQ2 (80.0 mmol) in CH2C12 (200 mL) was stirred at room temperature for 6 h. After filtering off the black solid, the resulting intermediate aldehyde 2 wasdissolved in CH3OH (100 mL). The NaOMe (15.0 mmol) and 1- cyclopropylethan-1-one (16.0 mmol) were added at room temperature. The reaction mixture was allowed to react at reflux for 4 h. The resulting mixture was evaporated, dissolved in water, extracted with EtOAc, and purified by column chromatography to afford intermediate product 3 (65 % yield for steps).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,588-36-3, its application will become more common.

Reference:
Patent; THE SCRIPPS RESEARCH INSTITUTE; FENG, Yangbo; LOGRASSO, Philip; ZHENG, Ke; PARK, Chul Min; WO2015/84936; (2015); A1;,
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Pyrimidine – Wikipedia

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. 1111638-74-4, name is 4-(3-Iodo-1H-pyrazol-4-yl)-2-(methylthio)pyrimidine, molecular formula is C8H7IN4S, 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. Safety of 4-(3-Iodo-1H-pyrazol-4-yl)-2-(methylthio)pyrimidine

General procedure: To a solution of compound 5a (40 mg, 0.084 mmol) in dry THF (6 mL) was added 1 M TBAF in THF (0.17 muL). The reaction mixture was refluxed for 3.5 h and added to brine, extracted with EtOAc, dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by column chromatography over silica gel (CH2Cl2-MeOH) to afford compound 6a (23.3 mg, 81%) as a yellow solid.

With the rapid development of chemical substances, we look forward to future research findings about 1111638-74-4.

Reference:
Article; Sekimata, Katsuhiko; Sato, Tomohiro; Sakai, Naoki; Watanabe, Hisami; Mishima-Tsumagari, Chiemi; Taguri, Tomonori; Matsumoto, Takehisa; Fujii, Yoshifumi; Handa, Noriko; Honma, Teruki; Tanaka, Akiko; Shirouzu, Mikako; Yokoyama, Shigeyuki; Miyazono, Kohei; Hashizume, Yoshinobu; Koyama, Hiroo; Chemical and Pharmaceutical Bulletin; vol. 67; 3; (2019); p. 224 – 235;,
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Adding a certain compound to certain chemical reactions, such as: 2227-98-7, 4-Aminopyrrolo[3,2-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, COA of Formula: C6H6N4, blongs to pyrimidines compound. COA of Formula: C6H6N4

[0071] (2R)-2-[({4-Amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl}methyl)amino]-3- (butylsulfanyl)propan-l-ol (Q.2). Compound Q.l (0.400 g, 1.32 mmol) was dissolved in MeOH (4 mL) and aq. hydrochloric acid (36%, 1 mL) was added. After 15 min the solvent was evaporated and the resulting gum dissolved in MeOH (10 mL) and neutralized with Amberlyst A21 resin then passed through a short column of the same resin and eluted with MeOH. The fractions containing product were evaporated to an oily residue that was dissolved in tert butanol (4 mL) then 9-deazaadenine (0.177 g, 1.32 mmol) and aq. formaldehyde solution (37%, 0.12 mL, 1.60 mmol) added and the mixture stirred at 70 C for 16 h. Silica gel was added to absorb all the solvent then the solvent was evaporated and the residue chromatographed on silica gel (gradient of 5 – 15% 7M NH3/MeOH in CHC13) to give Q.2 as a colourless solid (0.131 g, 32%). XH NMR (500 MHz, CD3OD): delta 8.16 (s, 1H), 7.49 (s, 1H), 4.06 (d, J= 13.8 Hz, 1H), 3.97 (d, J= 13.9 Hz, 1H), 3.69 (dd, J= 11.2, 5.1 Hz, 1H), 3.63 (dd, J= 11.2, 5.4 Hz, 1H), 2.81-2.76 (m, 1H), 2.69 (dd, J= 13.5, 6.3 Hz, 1H), 2.53 (dd, J= 13.5, 6.9 Hz, 1H), 2.31 (ddd, J= 12.5, 8.0, 6.5 Hz, 1H), 2.25 (ddd, J= 12.5, 8.1, 6.7 Hz, 1H), 1.45-1.35 (m, 2H), 1.33-1.25 (m, 2H), 0.85 (t, J = 7.3 Hz, 3H). 13C NMR (125.7 MHz, CD3OD, centre line delta 49.0): delta 152.1 (C), 150.9 (CH), 146.6 (C), 129.1 (CH), 115.5 (C), 114.6 (C), 63.9 (CH2), 57.8 (CH), 41.2 (CH2), 34.5 (CH2), 32.7 (CH2), 32.6 (CH2), 22.9 (CH2), 13.9 (CH3). ESI-HRMS calcd for Ci4H24N5OS+, (M+H)+, 310.1697, found 310.1702.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,2227-98-7, 4-Aminopyrrolo[3,2-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; ALBERT EINSTEIN COLLEGE OF MEDICINE OF YESHIVA UNIVERSITY; SCHRAMM, Vern, L.; CLINCH, Keith; GULAB, Shivali, Ashwin; WO2015/123101; (2015); A1;,
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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. 42839-09-8, name is 2-Pyrimidinemethanol. A new synthetic method of this compound is introduced below., Recommanded Product: 2-Pyrimidinemethanol

Also, reacting 2-hydroxymethylpyrimidine with 3-mercaptopropylamine by the procedure of Example 1 and then reacting the resulting 2-[(3-aminopropyl)thiomethyl]-pyrimidine with dimethyl-N-cyanoimidodithiocarbonate and methylamine by the procedure of Example 3(d) gives N-cyano-N’-methyl-N”-[3-(2-pyrimidylmethylthio)propyl]guanidine.

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, 42839-09-8, 2-Pyrimidinemethanol.

Reference:
Patent; Smith Kline & French Laboratories Limited; US3950333; (1976); A;,
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Pyrimidine – Wikipedia

Synthetic Route of 4270-27-3, Adding some certain compound to certain chemical reactions, such as: 4270-27-3, name is 6-Chloropyrimidine-2,4(1H,3H)-dione,molecular formula is C4H3ClN2O2, 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 4270-27-3.

6-chloro-uracil (7 g, 1 eq.), methyl iodide (8.9 ml, 3 eq.) and anhydrous potassium carbonate (3.36 g, 0.5 eq.) were stirred in 30 ml of dimethylsulfoxide at room temperature for 3 h, then 38 ml of water was added and stirred in ice bath for 2 h. A white solid precipitated and the precipitate was collected by filtration and dried to give 5.12 g of a solid. MS (ESI): 161(M+H)

According to the analysis of related databases, 4270-27-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shanghai Institute Of Materia Medica Chinese Academy of Sciences; SHEN, Jianhua; WANG, Yiping; CHEN, Xinde; XU, Wenwei; WANG, Kai; (84 pag.)EP3239135; (2017); A1;,
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Pyrimidine – Wikipedia

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 941685-26-3, name is 4-Chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C12H18ClN3OSi

A 1000 mL round bottom flask was charged with 4-chloro-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine (10.00 g, 35.23 mmol), 1-butanol (25.0 mL), 1-(1-ethoxyethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (15.66 g, 52.85 mmol), water (25.0 mL) and potassium carbonate (12.17 g, 88.08 mmol). This solution was degased 4 times, filling with nitrogen each time. To the solution was added tetrakis(triphenylphosphine)palladium(0) (4.071 g, 3.523 mmol). The solution was degased 4 times, filling with nitrogen each time. The mixture was stirred overnight at 100 C. After being cooled to room temperature, the mixture was filtered through a bed of celite and the celite was rinsed with ethyl acetate (42 mL). The filtrate was combined, and the organic layer was separated. The aqueous layer was extracted with ethyl acetate. The organic extracts were combined and concentrated under vacuum with a bath temperature of 30-70 C. to give the final compound 4-(1H-pyrazol-4-yl)-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine. Yield: 78%. LC-MS: 316.2 (M+H)+.

With the rapid development of chemical substances, we look forward to future research findings about 941685-26-3.

Reference:
Patent; Huang, Taisheng; Xue, Chu-Biao; Wang, Anlai; Kong, Ling Quan; Ye, Hai Fen; Yao, Wenqing; Rodgers, James D.; Shepard, Stacey; Wang, Haisheng; Shao, Lixin; Li, Hui-Yin; Li, Qun; US2011/224190; (2011); A1;,
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Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 90914-41-3, 3-Bromo-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, Recommanded Product: 90914-41-3, blongs to pyrimidines compound. Recommanded Product: 90914-41-3

Step 5: Synthesis of 4-(4-((1-(3-bromo-1H-pyrazolo[3,4-d]pyrimidin-4-yl)piperidin-4-yl)amino)-6-methoxynaphthalen-2-yl)-N,N-dimethylpyrimidin-2-amine (144): To a solution of 4-(6-methoxy-4-(piperidin-4-ylamino)naphthalen-2-yl)-N,N-dimethylpyrimidin-2-amine (143) (196 mg, 0.43 mmol) and triethylamine (0.5 ml) in anhydrous tetrahydrofuran (8 ml) was added 3-bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine (122 mg, 0.52 mmol). The mixture was stirred at 50 C. for 24 hours before being poured into ethyl acetate (150 ml) washed with water (300 ml) and the organic layer dried over anhydrous magnesium sulfate. Evaporation to dryness gave a yellow foam that was crystallized from dichloromethane and ethyl acetate to give 4-(4-((1-(3-bromo-1H-pyrazolo[3,4-d]pyrimidin-4-yl)piperidin-4-yl)amino)-6-methoxynaphthalen-2-yl)-N,N-dimethylpyrimidin-2-amine (144) as a yellow solid (145 mg) M.p.=167-172 C. 1H NMR (DMSO-d6) 400 MHz delta 8.4-8.33 (m, 2H), 7.9-7.8 (m, 2H), 7.52 (m, 2H), 7.24-7.2 (m, 1H), 7.15-7.12 (m, 1H), 5.9-5.74 (m, 1H), 4.56-4.53 (m, 2H), 3.95 (s, 1H), 3.9 (s, 3H), 3.41-3.26 (m, 2H), 3.22 (s, 6H), 2.28-2.25 (m, 2H), 1.97-1.75 (m, 2H), LCMS m/e 574 and 576 (M+) Calculated for C27H28BrN9O.CH2Cl2: C, 51.00; H, 4.59; N, 19.12; found C 51.00, H 4.39, N 18.85.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,90914-41-3, 3-Bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; ArQule, Inc.; US2011/166137; (2011); A1;,
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Pyrimidine – Wikipedia

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. 55583-59-0, name is 2,5-Diamino-4,6-dichloropyrimidine, the common compound, a new synthetic route is introduced below. Formula: C4H4Cl2N4

In the reaction vessel, 4,6-dichloropyrimidine-2,5-diamine(501 mg, 2.79 mmol),Benzofuran-2-boronic acid (1.05 g, 6.46 mmol),Sodium carbonate (1.48 g, 14.0 mmol),And tetrakis (triphenylphosphine) palladium (0)To a solution of (161 mg, 0.140 mmol) in toluene (28 mL), ethanol (7 mL) and distilled water (7 mL) are added at room temperature, and the reaction solution is stirred under an argon atmosphere for 20 hours under heat reflux Was cooled to room temperature. Add distilled water (8 mL) and stir,The separated aqueous layer was extracted three times with ethyl acetate (12 mL).Thereafter, the whole organic layer is combined, saturated aqueous sodium chloride solution (12 mL) is added thereto, the mixture is stirred and washed, anhydrous sodium sulfate is added to the separated organic layer for dehydration, and the filtrate after filtration is concentrated under reduced pressure. Flash column chromatography of the obtained concentratePurified with (silica gel, n-hexane / ethyl acetate),4,6-Di (benzofuran-2-yl) pyrimidine-2, 5-diamine(0.748 g, 78% yield)

The synthetic route of 55583-59-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Microbial Chemistry Research Foundation; Kumagai, Naoya; Noda, Hidetoshi; Asada, Yasuko; Shibazaki, Masakatsu; (48 pag.)JP2019/64981; (2019); A;,
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Reference of 25193-95-7, Adding some certain compound to certain chemical reactions, such as: 25193-95-7, name is 5-(Hydroxymethyl)pyrimidine,molecular formula is C5H6N2O, 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 25193-95-7.

To a solution of pyrimidin-5-yl-methanol (100 mg, 0.91 mmol, 1.0 equiv; [CASRN 25193-95-7])in anhydrous THF (6 mL) and NEt3 (97 mg, 0.13 mL, 0.95 mmol, 1.05equiv) at 0C was added slowly a solution of methanesulfonyl chloride (104 mg,0.071 mL, 0.91 mmol, 1.0 equiv) dissolved in THF (1 mL). After 30 min, sodiumiodide (136 mg, 0.91 mmol, 1.0 equiv) was added and stirring at 0C continuedfor another 30 min, then the cooling bath was removed and the reaction allowedto reach rt. After 1 h, the reaction was again cooled down to 0C and asolution of 3-(4-trifluoromethyl-phenyl)-prop-2-yn-1-ol (182 mg, 0.91 mmol, 1.0equiv; [CAS RN 173546-21-9]) in THF (3 mL) was added, followed bytreatment with potassium tert-butoxide(239 mg, 2.09 mmol, 2.3 equiv). After 1 h, the reaction mixture was allowed toreach rt and stirring continued for 18 h. The reaction was quenched by addition of a 10%solution of KH2PO4 (50 mL) and the crude product extracted with diethylether (3x 50 mL). The combined organic layers were dried over MgSO4,concentrated under reduced pressure and the product purified by MPLC elutingwith a gradient of heptane / ethyl acetate. The title compound was isolated aslight yellow solid (56 mg, 21%). 1H NMR (600 MHz, [D6]DMSO): d = 4.56 (s, 2H), 4.70 (s, 2H), 7.66 – 7.72 (m, 2H), 7.74 – 7.78 (m, 2H),8.84 (s, 2H), 9.15 (s, 1H). 13C NMR (150 MHz, [D6]DMSO): d = 58.6, 66.6, 84.9, 88.5, 123.9 (q, JCF = 274.9 Hz), 125.6 (q, JCF = 3.8 Hz), 126.0, 128.8 (q, JCF = 32.0 Hz), 131.3, 132.2, 156.5, 157.9.19F NMR (375 MHz, [D6]DMSO): d = -61.4. HRMS (ESI+): m/z [M]+calcd for C15H11F3N2O: 292.0824,found: 292.0827.

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. 25193-95-7, 5-(Hydroxymethyl)pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Martin, Rainer E.; Lenz, Mario; Alzieu, Thibaut; Aebi, Johannes D.; Forzy, Liliane; Tetrahedron Letters; vol. 54; 49; (2013); p. 6703 – 6707;,
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