Day: March 16, 2021

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 76196-80-0, name is Methyl 5-methylpyrimidine-2-carboxylate. This compound has unique chemical properties. The synthetic route is as follows. Formula: C7H8N2O2

A mixture of methyl 5-methylpyrimidine-2-carboxylate (0.500 g, 3.286 mmol), 1-bromopyrrolidine-2,5-dione (NBS, 0.643 g, 3.615 mmol) and Azobisisobutyronitrile (AIBN, 0.216 g, 1.3 14 mmol) in carbon tetrachloride (4 mL) prepared at the room temperature was heated at reflux for 10 hr, and cooled down to the ambient temperature. Then, water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with aqueous saturated sodium chloride solution, dried with anhydrous MgSO4, filtered, and concentrated in vacuo. The residue was chromatographed (Si02, 12 g cartridge; ethyl acetate / hexane = 0 % to 30 %) to give methyl 5-(bromomethyl)pyrimidine-2-carboxylate as white solid (0.380 g, 50.0%).

With the rapid development of chemical substances, we look forward to future research findings about 76196-80-0.

Reference:
Patent; CHONG KUN DANG PHARMACEUTICAL CORP.; LEE, Jaekwang; HAN, Younghue; KIM, Yuntae; CHOI, Daekyu; MIN, Jaeki; BAE, Miseon; YANG, Hyunmo; KIM, Dohoon; (644 pag.)WO2017/18803; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 330786-24-8, Adding some certain compound to certain chemical reactions, such as: 330786-24-8, name is 3-(4-Phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine,molecular formula is C17H13N5O, 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 330786-24-8.

3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (120.00 mg, 395.62 mumol) was weighed into a single-mouth flask and anhydrous tetrahydrofuran (10 ml) was added. , triphenylphosphine (311.30 mg, 1.19 mmol), cyclopentanol (34.08 mg, 395.62 mumol), diethyl azodicarboxylate (239.99 mg, 1.19 mmol) were added under argon atmosphere, and the reaction was monitored by TLC at room temperature overnight. complete. The reaction solution was concentrated and column chromatography afforded 117.00 mg of BTK-7 in a yield of 79.62%.

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. 330786-24-8, 3-(4-Phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Shanghai Institute of Technology; Yao Zhiyi; Yang Yan; Xia Xiaoming; Xue Nannan; Shu Qisheng; Wang Qingxuan; Wang Dongsheng; (7 pag.)CN107827892; (2018); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 1013916-37-4, 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 1013916-37-4, name is 2-Chloro-8-cyclopentyl-5-methylpyrido[2,3-d]pyrimidin-7(8H)-one. This compound has unique chemical properties. The synthetic route is as follows.

To a glass lined vessel was added 2-chloro-8-cyclopentyl-5-methyl-8/-/-pyrido[2,3-c]pyrimidin-7- one (9.35 g, 1.0 equiv.) along with acetonitrile (65 mL, 7.0 vol). N-Bromosuccinimide (9.67 g, 1.5 equiv.) and oxalic acid (0.65 g, 0.2 equiv.) were added. The reaction mixture was heated to 60¡À5 C. The reaction was stirred at 60C until starting material was consumed (at least 6 hours). The slurry was cooled to 20C and H20 (9 mL, 1 vol) was added. To the slurry was added a solution of sodium bisulfite (3.88 g, 1.0 equiv) in H20 (38 mL, 4 vol). The slurry was granulated for 1 hour, then filtered directly onto a 2 Whatman paper filter. The reaction vessel was washed with water (19 mL, 2 vol) followed by a 7:3 mix of methanol/acetonitrile (28 mL, 3 vol), and the washes were transferred onto the filter cake. The product was dried in the vacuum oven at 50-55C. 6-Bromo-2-chloro-8-cyclopentyl-5-methyl-8/-/-pyrido[2,3-c]pyrimidin-7-one (10.52 g; 87%) was isolated as a pale yellow solid.The product was further purified by recrystallization from toluene and n-heptanes. Toluene (60 mL, 6 vol) and 6-bromo-2-chloro-8-cyclopentyl-5-methyl-8/-/-pyrido[2,3-c]pyrimidin- 7-one (10.00 g, 1 equiv) were added to a reaction vessel and heated to 80C. The warm reaction mixture was filtered through an appropriate cartridge to ensure the removal of insoluble Pd and other insoluble contaminants. The filter cartridge was washed with 80C toluene (5 mL, 0.5 vol). The slurry was cooled to 25C at 1 C/min. n-Heptane (70 mL, 7 vol) was added to the reaction slurry at 1 mL/min. The slurry was further cooled to 0C at 1 C/min. The slurry was granulated at 0C for at least 1 hour.The slurry was filtered directly onto a 2 Whatman paper filter. n-Heptane (30 mL, 3 vol) was charged to the reaction vessel and the wash was transferred onto the filter cake and the product was dried in the vacuum oven at 50-55C. 6-Bromo-2-chloro-8-cyclopentyl-5-methyl-8/-/- pyrido[2,3-c]pyrimidin-7-one (8.73 g, 87%) was isolated as a cream colored solid.1H NMR (500 MHz, DMSO-de): delta 9.20 (s, 1 H), 5.82 (m, 1 H), 2.65 (s, 3H), 2.11 (m, 2H), 2.04 (m, 2H), 1.86 (m, 2H), 1.64 (m, 2H);13C NMR (125 MHz, DMSO-cfe): delta 158.2, 158.2, 157.6, 154.1 , 144.0, 120.9, 113.0, 54.4, 28.3, 25.7, 18.3; HRMS: Calcd for dsHuNsOi BnCli (M+H)+: 342.00033, Found: 342.00037.

According to the analysis of related databases, 1013916-37-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER INC.; CHEKAL, Brian Patrick; IDE, Nathan D.; WO2014/128588; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 1152475-42-7, 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. 1152475-42-7, name is 7-Bromo-2-chlorothieno[3,2-d]pyrimidine, molecular formula is C6H2BrClN2S, 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.

7-Bromo-2-chlorothieno[3,2-d]pyrimidine (200 mg, 0.81 mmol) was dissolved in 2-butanol (4 mL) and then potassium carbonate (223 mg, 1.61 mmol) and 3,4,5-trimethoxybenzenamine (110 mg, 0.81 mmol) were added. After blowing nitrogen to the reaction mixture for 10 minutes, Pd2(dba)3 (50 mg, 0.048 mmol) and Xphos (35 mg, 0.073 mmol) were added. The reaction mixture was stirred at 80 C for 2.5 hours and then filtered with celite. The filtrate was diluted with ethyl acetate and washed with brine. The organic layer was dried with magnesium sulfate, filtered with celite, and then concentrated. Purification by chromatography (15% ethyl acetate/hexane) yielded the target compound (120 mg, 43% yield). [0504] 1H NMR (300 MHz, DMSO-d 6) delta 9.42 (s, 1H), 8.33 (s, 1H), 7.85 (s, 1H), 6.65 (s, 2H), 3.76 (s, 6H), 3.60 (s, 3H), MS m/z: 352.45 [M+1].

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 1152475-42-7, 7-Bromo-2-chlorothieno[3,2-d]pyrimidine.

Reference:
Patent; KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY; SIM, Tae Bo; CHOI, Hwan Geun; HAH, Jung Mi; HAM, Young Jin; JUN, Eun Jin; LEE, Jung Hun; KIM, Hwan; WO2011/49332; (2011); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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;,
Pyrimidine | C4H4N2 – PubChem,
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;,
Pyrimidine | C4H4N2 – PubChem,
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;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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;,
Pyrimidine | C4H4N2 – PubChem,
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;,
Pyrimidine | C4H4N2 – PubChem,
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;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia