Pyrimidines

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. 58347-49-2, name is 7-Chloropyrazolo[1,5-a]pyrimidine, molecular formula is C6H4ClN3, 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. Recommanded Product: 58347-49-2

EXAMPLE 46(S)-A- { 5,7-Difluoro-3 -[ 1 -(pyrazolof 1 ,5 -alpha]pyrimidin-7-ylamino)ethyllquinolin-2-yl} – piperazin-2-oneA solution of Intermediate 30 (61.2 mg, 0.20 mmol), 7-chloropyrazolo[l,5-alpha]- pyrimidine (33.8 mg, 0.2 mmol) and DIPEA (28.5 mg, 0.22 mmol) in M-BuOH (3 mL) was heated at 12O0C for 16 h. The solvent was removed in vacuo and the residue purified by preparative HPLC to afford the title compound (14.9 mg, 18%) as a cream solid. 6H (CDCl3) 8.45 (IH, s), 8.13 (IH, d, J5.2 Hz), 8.02 (IH, s), 7.35 (IH, dd, J 8.8 Hz), 6.90 (IH, t, J8.8 Hz), 6.88 (IH, d, J6.4 Hz), 6.55 (IH, br s), 6.48 (IH, s), 5.89 (IH, d, J5.2 Hz), 5.12-5.18 (IH, m), 4.09 (2H, q, J 17.5 Hz), 3.52-3.68 (4H, m), 1.88 (3H, d, J6.8 Hz). LCMS (ES+) 424 (M+H)+, RT 3.07 minutes {Method 1).

With the rapid development of chemical substances, we look forward to future research findings about 58347-49-2.

Reference:
Patent; UCB PHARMA S.A.; ALLEN, Daniel, Rees; BROWN, Julien, Alistair; BUeRLI, Roland; HAUGHAN, Alan, Findlay; LANGHAM, Barry, John; MATTEUCCI, Mizio; OWENS, Andrew, Pate; RAPHY, Gilles; SHARPE, Andrew; WO2010/133836; (2010); A1;,
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Related Products of 100644-65-3, 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. 100644-65-3, name is 4-Chloro-1H-pyrazolo[3,4-d]pyrimidin-6-amine, molecular formula is C5H4ClN5, 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.

Sodium hydride (60% dispersion in mineral oil) (354 mg, 8.85 mmol) was added portionwise to a yellow suspension of 4-chloro- 1 H-pyrazolo [3 ,4-d]pyrimidin-6- amine (A-2) (1.25 g, 7.34 mmol) in dry DMF (5 mL). l-Bromo-2-chloroethane (3.68 mL, 44.2 mmol) was added dropwise. The resulting mixture was stirred for 2 h at room temperature. The DMF was evaporated. The residue was purified by chromatography on silica gel (eluant: 0-10% methanol/ CH2C12 gradient). The product was washed with hexanes and filtered to give 4-chloro-l-(2-chloroethyl)-lH-pyrazolo[3,4-d]pyrimidin-6- amine (A-3) (409 mg, 24% yield). NMR (500 MHz, CDC13) delta ppm 3.96 (t, 2H, J=6.5 Hz), 4.59 (t, 2H, J=6.5 Hz), 5.34 (s, 2H), 7.93 (s, 1H). MS (M+l): 232, 233, 234 (2 CI).

According to the analysis of related databases, 100644-65-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; TING, Pauline, C.; MA, Shuguang; BLUMENKRANTZ, Neil; CHOWDBURY, Swapan; NEUSTADT, Bernard, R.; WO2012/135084; (2012); A1;,
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Application of 62802-42-0, 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 62802-42-0 as follows.

Step 1 : 1,1-Dimethylethyl [1-(2-fluoro-5-pyrimidinyl)-4-piperidinyl]carbamate (194)To a stirred solution of 1 ,1-dimethylethyl 4-piperidinylcarbamate (500 mg, 2.50 mmol) and diisopropylethylamine (0.871 mL, 5.0 mmol) in acetonitrile (25 mL) was added 2- chloro-5-fluoropyrimidine (0.34 mL, 2.75 mmol) via syringe at RT. The reaction mixture was heated to reflux for 19 hours, then cooled to RT and concentrated under reduced pressure. The crude oil was purified by SiO2 flash chromatography (20% to 50% EtOAc in hexanes) to give 495 mg (67%) of the title product 194 as a viscous oil. 1H NMR (400 MHz, CDCI3): delta 8.17 (s, 2 H), 4.56 – 4.52 (m, 2 H), 4.47 – 4.41 (m, 1 H), 3.70 (br s, 1 H), 3.07 – 3.00 (m, 2 H), 2.02 – 1.98 (m, 2 H), 1.44 (s, 9 H), 1.39 -1.28 (m, 2 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,62802-42-0, its application will become more common.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2008/8895; (2008); A1;,
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Synthetic Route of 63810-78-6, 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. 63810-78-6, name is 5-Bromo-4-chloro-2-(methylthio)pyrimidine. A new synthetic method of this compound is introduced below.

Compound 44. A mixture of compound 42 (1.0 g, 4.22 mmol, 1.5 eq.), compound 43 (1.2 g, 2.82 mmol, 1 eq.), Pd(PPh3)4 (325 mg, 282 mumol, 0.1 eq.), and LiCl (239 mg, 5.63 mmol, 2 eq.) in toluene (10 mL) was degassed and purged with N2 for 3 times. Then the mixture was stirred at 100 C for 8 h under N2. The reaction mixture was cooled down to 25 oC and partitioned between sat. KF (30 mL) and EtOAc (40 mL). The organic phase was separated, washed with brine (20 mL), dried over Na2SO4, and concentrated in vacuo. The residue was purified by column chromatography (PE/EtOAc: 10/1 to 3/1) to afford compound 44 (400 mg, 1.18 mmol, 42% yield). 1H NMR (CDCl3, 400 MHz) delta 8.72 (s, 1H), 4.11 (s, 3H), 3.00 (d, J = 6.7 Hz, 2H), 2.57 (s, 3H), 1.07-0.92 (m, 1H), 0.57-0.46 (m, 2H), 0.32-0.17 (m, 2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,63810-78-6, 5-Bromo-4-chloro-2-(methylthio)pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; YISSUM RESEARCH DEVELOPMENT COMPANY OF THE HEBREW UNIVERSITY OF JERUSALEM LTD.; SNIR-ALKALAY, Irit; VACCA, Joseph; BEN-NERIAH, Yinon; (238 pag.)WO2019/155468; (2019); A1;,
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Synthetic Route of 84905-80-6, 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.84905-80-6, name is 4-Chloro-5H-pyrrolo[3,2-d]pyrimidine, molecular formula is C6H4ClN3, molecular weight is 153.57, as common compound, the synthetic route is as follows.

Step 3: Preparation of 7-bromo-4-chloro-5H-pyrrolo[3,2-d]pyrimidine Tetrahydrofuran (5 mL) and N-bromosuccinimide (116 mg) were added to 4-chloro-5H-pyrrolo[3,2-d]pyrimidine (100 mg). The mixture was stirred for 1 hr and, upon completion of the reaction, ethyl acetate was added thereto, and washed with water. The mixture was dried over anhydrous sodium sulfate, filtered and distilled under reduced pressure to obtain the title compound. 1H NMR (300 MHz, DMSO-d6): delta 12.95 (s, 1 H), 8.71 (s, 1 H), 8.24 (d, 1 H)

Statistics shows that 84905-80-6 is playing an increasingly important role. we look forward to future research findings about 4-Chloro-5H-pyrrolo[3,2-d]pyrimidine.

Reference:
Patent; Hanmi Pharmaceutical Co., Ltd.; PARK, Chul Hyun; KIM, Won Jeoung; JUNG, Young Hee; KIM, Nam Du; CHANG, Young Kil; KIM, Maeng Sup; EP2738174; (2014); A2;,
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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.7504-94-1, name is 2-Hydrazinylpyrimidine, molecular formula is C4H6N4, molecular weight is 110.1172, as common compound, the synthetic route is as follows.HPLC of Formula: C4H6N4

After adding 40 mg of 2-dimethylaminoethanol, 120 mg of triphenylphosphine and 0.200 ml of DEAD (2.2 M, toluene solution) to a 1 ml THF solution containing 100 mg of {2-(3-hydroxy-5-methoxyphenyl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene}carbamic acid methyl ester (Example (4c)) at 0 C., the mixture was stirred at room temperature for 16 hours and 30 minutes. The reaction mixture was concentrated, and the residue was crudely purified by silica gel column chromatography (ethyl acetate-heptane) to give 55 mg of a crude product. To a 1 ml DMF solution containing 55 mg of the obtained crude product there were added 12 mg of 2-hydrazinopyrimidine and 0.015 ml of triethylamine, and the mixture was stirred at 85 C. for 11 hours and 30 minutes under a nitrogen atmosphere. The reaction mixture was concentrated, and the residue was dissolved in 0.8 ml of methanol, 0.8 ml of THF and 0.1 ml of acetic acid. Next, 100 mg of sodium cyanotrihydroborate was added to the solution and the mixture was stirred at room temperature for 3 hours and 30 minutes. The reaction mixture was crudely purified by reverse-phase high performance liquid chromatography (acetonitrile-water, 0.1% acetic acid) to give a crude product. To a solution of the obtained crude product in 2.4 ml of a methanol:water:acetic acid=1:1:1 mixed solvent there was added 100 mg of iron powder, and the mixture was stirred at 65 C. for 18 hours and 30 minutes under a nitrogen atmosphere. After filtering the reaction mixture, it was crudely purified by reverse-phase high performance liquid chromatography (acetonitrile-water, 0.1% acetic acid) to give a crude product. The obtained crude product was optically resolved using a SUMICHIRAL OA-2500 column, and the first eluting enantiomer (4.35 mg) of the title compound was obtained as a light yellow solid. 1H-NMR (CD3OD) delta 1.92 (s, 6H) 2.49 (s, 6H) 2.96 (dd, J=5.2, 5.6 Hz, 2H) 3.76 (s, 3H) 4.14 (dd, J=5.2, 5.6 Hz, 2H) 5.58 (s, 1H) 6.47 (t, J=2.0 Hz, 1H) 6.77 (t, J=2.0 Hz, 2H) 6.85 (d, J=8.8 Hz, 2H) 7.30 (t, J=4.8 Hz, 1H) 7.60 (d, J=8.8 Hz, 2H) 8.77 (d, J=4.8 Hz, 2H) HPLC retention time: 11 min

At the same time, in my other blogs, there are other synthetic methods of this type of compound,7504-94-1, 2-Hydrazinylpyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Eisai R&D Management Co., Ltd.; US2008/15199; (2008); A1;,
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Pyrimidine – Wikipedia

Electric Literature of 3680-69-1 ,Some common heterocyclic compound, 3680-69-1, molecular formula is C6H4ClN3, 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.

[To a suspension of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (F-1) (3.99 g, 26.0 mmol, 1.0 eq) in anhydrous DCM (150 mL) under argon, N-bromosuccinimide (6.02 g, 33.8 mmol, 1.3 eq) is added and the resulting mixture is stirred at RT for 3 h. The reaction mixture is diluted with MeOH (30 mL) and then concentrated in vacuo. The residue is triturated with H2O (150 mL). This is collected by filtration and then re-crystallized in MeOH to afford the product, 5-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine (G-1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3680-69-1, its application will become more common.

Reference:
Patent; Ren, Pingda; Liu, Yi; Li, Liansheng; Chan, Katrina; Wilson, Troy Edward; Castro, Alfredo C.; Evans, Catherine A.; Snyder, Daniel A.; US2012/122838; (2012); A1;,
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Pyrimidine – Wikipedia

Electric Literature of 1211443-61-6, Adding some certain compound to certain chemical reactions, such as: 1211443-61-6, name is 2-Chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide,molecular formula is C14H17ClN4O, 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 1211443-61-6.

To a suspension of 2-chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide (5) (500 mg, 1.71 mmol) in 10 mL 1,4-dioxane was added 2-Amino-5-nitropyridine (356 mg, 2.56 mmol), Pd(OAc)2 (9.6 mg, 0.043 mmol), BINAP (53 mg, 0.09 mmol) and Cs2CO3 (834 mg, 2.56 mmol) and the flask was purged with Ar. Then the flask was sealed and the mixture was heated for 12 h at 100. The reaction was cooled to room temperature, the solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 200 mg (30%) of 7 as a yellow solid. 1H NMR (400 MHz, Chloroform-d) delta 9.29 (d, J = 2.7 Hz, 1H), 8.90 (s, 1H), 8.66 (d, J = 9.3 Hz, 1H), 8.47 (dd, J = 9.4, 2.8 Hz, 1H), 7.26 (s, 1H), 6.55 (s, 1H), 4.84 (p, J = 8.9 Hz, 1H), 3.18 (s, 6H), 2.63 – 2.47 (m, 2H), 2.24 – 2.02 (m, 4H), 1.90 – 1.66 (m, 2H).

According to the analysis of related databases, 1211443-61-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Li, Yongtao; Guo, Qingxiang; Zhang, Chao; Huang, Zhi; Wang, Tianqi; Wang, Xin; Wang, Xiang; Xu, Guangwei; Liu, Yanhua; Yang, Shengyong; Fan, Yan; Xiang, Rong; Bioorganic and Medicinal Chemistry Letters; vol. 27; 15; (2017); p. 3231 – 3237;,
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Adding a certain compound to certain chemical reactions, such as: 4489-34-3, 4,6-Dichloro-2-methylsulfonylpyrimidine, 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: 4,6-Dichloro-2-methylsulfonylpyrimidine, blongs to pyrimidines compound. Recommanded Product: 4,6-Dichloro-2-methylsulfonylpyrimidine

General procedure: The general synthetic route for the preparation of tozasertib (a-d) and tozasertib analogs (B: a, e-g; A: a, h-j) is shown in Fig. 1. Reagents and conditions: (a) 3-chloroperoxybenzoic acid, DCM, rt, 3h; (b) N-(4- mercaptophenyl)cyclopropanecarboxamide, TEA, CH3CN, 80 C, 3-1 Oh; (c) 5-methyl- 1 H-pyrazol-3-amine, DIPEA, DMF, 95 C, 16h; (d) amine (1-methylpiperazine or morpholine), DMF, DIPEA, 90 C, 6-12h; (e) corresponding thiol, TEA, CH3CN, 80 C, 3-1 Oh; (f) 5-methyl-1 H-pyrazol-3-amine, DIPEA, dioxane, 95 C, 3-6 h, (g) amine (1-methylpiperazine or morpholine), DMF, DIPEA, 90 C, 6-12h; (h) thiophenol, TEA, THF, 50 C; (i) corresponding amine, DIPEA, dioxane, 95 C, 3-6 h; (j) amine (1- methylpiperazine or morpholine), DMF, DIPEA, 90 C, 6-12h. (0097) The structures and batch purities (>90%) of the compounds have been confirmed by using standard analytical methods (LC/MS and NMR).

The synthetic route of 4489-34-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOMED X GMBH; SAMEH, Eid; FULLE, Simone; MERGET, Benjamin; TURK, Samo; (43 pag.)WO2019/101843; (2019); 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. 2434-53-9, name is 6-Amino-1-methylpyrimidine-2,4(1H,3H)-dione. A new synthetic method of this compound is introduced below., Safety of 6-Amino-1-methylpyrimidine-2,4(1H,3H)-dione

General procedure: A solution of 6-aminouracils 1 (1.0mmol), alpha-azidochalcones 2 (1.0mmol), and NEt3 (0.5mmol) in DMF (4mL) was heated at 50C for 30min. After completion of the reaction which was monitored by TLC, the mixture was cooled down to room temperature. Then, water (10mL) was added to the mixture and extracted three times with EtOAc (3¡Á15mL). The combined organic extracts were washed with brine, dried over Na2SO4 and then concentrated. The precipitate was filtered and washed with Et2O to afford pure product 3.

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, 2434-53-9, 6-Amino-1-methylpyrimidine-2,4(1H,3H)-dione.

Reference:
Article; Adib, Mehdi; Peytam, Fariba; Rahmanian-Jazi, Mahmoud; Mahernia, Shabnam; Bijanzadeh, Hamid Reza; Jahani, Mehdi; Mohammadi-Khanaposhtani, Maryam; Imanparast, Somaye; Faramarzi, Mohammad Ali; Mahdavi, Mohammad; Larijani, Bagher; European Journal of Medicinal Chemistry; vol. 155; (2018); p. 353 – 363;,
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