Day: November 23, 2020

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 5750-76-5, name is 2,4,5-Trichloropyrimidine. This compound has unique chemical properties. The synthetic route is as follows. 5750-76-5

General procedure: Take 6 (23.44 mmol) and DIPEA (4.5 g, 35.16 mmol) in 50 mL dioxane was slowly added 5 (3.8 g, 23.44 mmol), warmed to 60 C. After the reaction for 5 hours, the reaction was completed, cooled, 400 mL of water was added to precipitate a yellow-white solid, suction filtered and dried to give a white solid which was directly used in the next reaction without further purification.

Statistics shows that 5750-76-5 is playing an increasingly important role. we look forward to future research findings about 2,4,5-Trichloropyrimidine.

Reference:
Patent; Dalian Medical University; Ma Xiaodong; Ge Yang; Zhang Jianbin; Liu He; Huang Shanshan; Li Zhen; Wang Changyuan; Liu Zhihao; Peng Jinyong; Liu Kexin; (26 pag.)CN106565614; (2017); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

113583-35-0, 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 113583-35-0, name is 2-Methanesulfonyl-4,6-dimethoxypyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

This example is used to describe the pyrimidine salicylic acid compounds of the present invention and processes for their preparation.1 mmol of Compound A was dissolved in 30 mL of re-evaporated toluene, 2 mmol of potassium carbonate was added, reacted at 20 C for 2 hours, 4,6-dimethoxy-2-methylsulfonylpyrimidine (1 mmol) was added and reacted at 120C for 12 h. The solvent was distilled off under reduced pressure, and a small amount of water was added to completely dissolve the solid. The aqueous layer was washed with ether several times. The aqueous layer was acidified with concentrated hydrochloric acid to pH=1, extracted with dichloromethane, dried over anhydrous sodium sulfate, Acid compound A1. The yield of compound A1 from compound A was 78%

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 113583-35-0, 2-Methanesulfonyl-4,6-dimethoxypyrimidine.

Reference:
Patent; HUAZHONG NORMAL UNIVERSITY; YANG, GUANGFU; LIU, YUCHAO; CHEN, QIONG; CHEN, JIE; CUI, HAILAN; TANG, WEI; (17 pag.)CN104140397; (2016); B;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

3740-92-9, 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. 3740-92-9, name is 4,6-Dichloro-2-phenylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 1,3-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2(1H)-one (249 mg, 1 mmol), 4,6-dichloro-2-phenylpyrimidine (171 mg, 1.0 mmol), Pd(PPh3)4 (116 mg, 0.1 mmol), aqueous sodium carbonate (2.0 M, 1 mL, 2 mmol) in dioxane (5 mL) was stirred and heated at 100¡ã C. for 2 h. The reaction mixture was diluted with water and extracted with EtOAc (3*). The extracts were combined, washed with brine, dried (Na2SO4) and concentrated. The residue was purified by flash column chromatography (EA:Hex, 0-80percent) to provide the 173 mg (67percent) of the desired product as an off-white solid. 1H NMR (400 MHz, DMSO-d6) delta ppm 2.13 (s, 3 H) 3.61 (s, 3H) 7.51-7.66 (m, 4H) 8.01 (s, 1H) 8.29 (s, 1H) 8.49 (dd, J=7.83, 1.77 Hz, 2H) 8.87 (d, J=2.27 Hz, 1H). LCMS (M+H)+312.

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, 3740-92-9, 4,6-Dichloro-2-phenylpyrimidine.

Reference:
Patent; CELGENE QUANTICEL RESEARCH, INC.; Bennett, Michael John; Betancort, Juan Manuel; Boloor, Amogh; Kanouni, Toufike; Stafford, Jeffrey Alan; Veal, James Marvin; Wallace, Michael Brennan; (250 pag.)US2017/298040; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

4595-59-9, 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. 4595-59-9, name is 5-Bromopyrimidine. A new synthetic method of this compound is introduced below.

The5-bromo-pyrimidine (9.4 mmol) is dissolved in tetrahydrofuran steams again 30ml in. At -78 C lower, will n-BuLi (11.3 mmol) in drops to the reactionsystem, and stirring 30 minutes. N-methoxy-N-methyl acetamide (11.8 mmol) oftetrahydrofuran solution (15 ml) at -78 C in the system dropping, andstirring 1 hour. Under room temperature, add saturated ammonium chlorideaqueous solution, ethyl acetate extraction 3 times. Concentrated extract,column chromatography (ethyl acetate: petroleum ether = 1 the […] 10)separated to obtain title compound 175 mg per litre. 1 H-NMR (CDCl 3)delta 9.37 (1H, s), 9.24 (2H, s), 2.66 (3H, s).

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. 4595-59-9, 5-Bromopyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CHIA TAI TIANQING PHARMACEUTICALGROUP CO LTD; Beijing Centaurus Biopharma Technology?Co.,?Ltd.; XIAO, DENGMING; LIANG, ZHI; HU, YUANDONG; HU, QUAN; ZHANG, QINGHUI; HAN, YONGXIN; WANG, HUAN; PENG, YONG; KONG, FANSHENG; LUO, HONG; (60 pag.)CN103130792; (2016); B;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

1500-85-2, 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. 1500-85-2, name is 7H-Pyrrolo[2,3-d]pyrimidin-4-amine, molecular formula is C6H6N4, 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.

General procedure: Procedure G: To a solution of 7H-pyrrolo[2,3-d]pyrimidin-4-amine (1, 0.32 g, 2.39 mmol) and 2?-chloro-4?-methylspiro[cyclohexane-1,7?-pyrrolo[3,4-b]pyridin]-5?(6?H)-one (2, 0.6 g, 2.39 mmol) in 1,4-dioxane (15 mL) was added cesium carbonate (2.33 g, 7.17 mmol). The reaction mixture was purged with argon for 5 min. and then XanthPhos (69 mg, 0.11 mmol), XPhos (57 mg, 0.11 mmol), tris(dibenzylideneacetone)dipalladium(0) (109 mg, 0.11 mmol) and palladium acetate (27 mg, 0.11 mmol) were added and the reaction mixture purged for an additional 5 min. The purged reaction mixture was stirred at 100 C. for 4 h. After TLC showed completion, the reaction mixture was filtered through a bed of celite and the resulting filtrate was concentrated. The crude product was purified by preparative HPLC. The desired fractions were concentrated to dryness under vacuum to afford 2?-(4-amino-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-4?-methylspiro[cyclohexane-1,7?-pyrrolo[3,4-b]pyridin]-5?(6?H)-one as a yellow solid. Yield: 0.095 g, 11%;

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. 1500-85-2, 7H-Pyrrolo[2,3-d]pyrimidin-4-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; EFFECTOR THERAPEUTICS, INC.; Sprengeler, Paul A.; Reich, Siegfried H.; Ernst, Justin T.; Webber, Stephen E.; (55 pag.)US2017/121339; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

3934-20-1, 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. 3934-20-1, name is 2,4-Dichloropyrimidine. A new synthetic method of this compound is introduced below.

A mixture of 2,4-dichloroprymidine 5 (1.00g, 6.7mmol), phenylboronic acid (0.99g, 8.1mmol), (1,1?-bis(diphenylphosphino)ferrocene)dichloropalladium(II) (0.51g, 0.7mmol) and sodium carbonate (2.13g, 20.1mmol) in DMF/1,4-dioxane/water (4:2:1, 10mL) was degassed with nitrogen and stirred at 80C for 10h. After completion of the reaction, the reaction mixture was diluted with dichloromethane (50ml), washed with brine (30mL¡Á3), dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by chromatography (ethyl acetate/petroleum ether) on silica gel to give 8h as a white solid (70%): mp 87.7-88.2C; 1H NMR (400MHz, CDCl3) delta: 8.65 (d, J=5.3Hz, 1H), 8.11 (dd, J=8.1, 1.9Hz, 2H), 7.66 (d, J=5.3Hz, 1H), 7.58-7.51 (m, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,3934-20-1, 2,4-Dichloropyrimidine, and friends who are interested can also refer to it.

Reference:
Article; Sun, Wuji; Hu, Shengquan; Fang, Shubiao; Yan, Hong; Bioorganic Chemistry; vol. 78; (2018); p. 393 – 405;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

4595-59-9 , The common heterocyclic compound, 4595-59-9, name is 5-Bromopyrimidine, molecular formula is C4H3BrN2, 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.

General procedure: Benzyl bromide (1 mmol), alkyl halide (1.1 mmol), thiourea (1.2 mmol), and K2CO3(3 mmol) were added to 5 mL of DMF at 100 C. The reaction was stopped after the consumptionof the benzyl bromide, which was monitored by gas chromatography (GC). Then, the reaction mixture was diluted with de-ionized water and extracted with CH2Cl2. Thecombined organic extracts were dried over anhydrous MgSO4, filtered, and concentrated byrotary evaporation to generate a crude product. Purification by silica gel chromatographyeluting with n-hexane afforded pure thioethers.

The synthetic route of 4595-59-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lu, Xiaogang; Wang, Hongmei; Gao, Runli; Pei, Chengxin; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 190; 1; (2015); p. 45 – 52;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

49845-33-2 , The common heterocyclic compound, 49845-33-2, name is 2,4-Dichloro-5-nitropyrimidine, molecular formula is C4HCl2N3O2, 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.

A solution of methyl amine-ethanol(7.6ml) and N,N-diisopropylethylamine(13.2ml) were dissolved into 150ml dichloromethane. The mixture was added dropwise to a solution of 2,4-dichloro-5-nitropyrimidine(10.0g) in dichloromethane(30ml) at 0¡ãC. After the completion of the dropwise addition, the mixture was kept at the same temperature to react for half an hour. Purification was conducted by a column chromatography to obtain a yellow solid(8.3g) in a yield of 85.4percent.?1H NMR(400 MHz, CDCl3): delta 9.05(s, 1H), 8.41(s, 1H), 3.22(s, 3H)ppm.

According to the analysis of related databases, 49845-33-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Si Chuan University; CSPC Zhongqi Pharmaceutical Technology (Shijiazhuang) Co., Ltd.; YANG, Shengyong; WEI, Yuquan; EP2578584; (2013); 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. 7752-82-1, name is 5-Bromopyrimidin-2-amine. A new synthetic method of this compound is introduced below., 7752-82-1

To a solution of 2-amino pyridine (30 g, 0.31 mol) in DME (120 mL) was added chloro acetone (40.5 mL, 0.47 mol) at room temperature. The reaction mixture was heated to reflux, and then stirred for 48 hours. The volatiles were concentrated under reduced pressure. Then the residue was purified by column chromatography eluting with 1% MeOH/DCM to afford Int-2 (20 g, 48%) as a liquid. Mass (m/z): 133 [M++1]. 1H NMR (200 MHz, dmso-d6): delta8.05 (d, J=8.2 Hz, 1H), 7.35 (s, 1H), 7.1 (t, J=6.8 Hz, 1H), 6.7 (t, J=6.8 Hz, 1H), 6.5 (d, J=8.2 Hz, 1H), 2.45 (s, 3H). To a solution of Int-2 (10 g, 76.7 mmol) in acetonitrile (50 mL) was added N-iodo succinamide (20.4 g, 80 mmol) portion wise at room temperature and then stirred for 48 hours. The precipitated solid was filtered off. The crude material was re-crystallized from ethyl acetate/water to afford Int-3 (9 g, 49%) as solid. Mass (m/z): 259 [M++1]. 1H NMR (200 MHz, dmso-d6): delta 8.22 (d, J=8 Hz, 1H), 7.47 (d, J=7.2 Hz, 1H), 7.29 (t, J=7.0 Hz, 1H), 2.35 (s, 3H). To a solution of Int-3 (6.0 g, 29.2 mmol) in IPA-H2O (75 mL, 2:1) was added PdCl2(dppf).DCM (4.7 g, 5.8 mmol), followed by the addition of tert-butyl amine (3.1 g, 43.8 mmol) at room temperature and the resulting reaction mixture was degassed for 15 minutes. Then Int-4 (2.9 g, 18.6 mmol) was added to the reaction mixture at room temperature. The reaction mixture was heated to 100 C. and then stirred for 16 hours. The reaction mixture was diluted with water (100 mL), extracted with EtOAc (3¡Á100 mL), washed with water, brine and dried over anhydrous Na2SO4. The organic layer was concentrated under reduced pressure. The crude material was purified by column chromatography eluting with 1% MeOH/DCM to afford Int-5 (1.6 g, 28%). Mass (m/z): 244 [M++1]. 1H NMR (200 MHz, dmso-d6): delta 8.51 (t, J=5 Hz, 2H), 7.71 (s, 1H), 7.63-7.55 (m, 2H), 7.34 (t, J=7 Hz, 1H), 6.94 (t, J=7 Hz, 1H), 2.43 (s, 3H). To a stirred mixture of 5-bromo 2-aminopyrimidine (8 g, 45.97 mmol) in MeOH-CH3CN (200 mL) in a steel bomb were added Pd(CH3CN)2Cl (2.38 g, 9.19 mmol), racemic-BINAP (5.7 g, 9.19 mmol), DIPEA (10.4 mL, 53.7 mmol) at room temperature and then closed the steel vessel tightly. Then CO gas (100 psi) was purged into the steel bomb and the stirring was continued at 120 C. for 45 hours. The reaction mixture was allowed to room temperature. The reaction mixture was filtered through a pad of celite. The celite pad was washed with excess of methanol and the filtrate was concentrated under vacuum. The crude material was purified by column chromatography eluting with 0.75% MeOH/DCM to afford Int-6 (5 g, 71%) as solid. Mass (m/z): 154 [M++1]. 1H NMR (200 MHz, dmso-d6): delta 8.65 (s, 3H), 7.49 (brs, 2H), 3.58 (s, 3H) To a stirred mixture of Int-5 (3 g, 2.34 mmol) and Int-6 (1.8 g, 12.34 mmol) in 1,4-dioxane (90 mL) were added Pd(OAc)2 (279 mg, 1.23 mmol) and Xanthpos (710 mg, 1.23 mmol) followed by cesium carbonate (6 g, 18.5 mmol) at room temperature. The resulting mixture was degassed and stirred at reflux temperature for 30 hours. The reaction mixture was cooled to room temperature and then stirred for 15 minutes. The precipitated solids were filtered off, washed with water (2¡Á10 mL) and dried under vacuum. The crude material was purified by column chromatography eluting with 1.5% MeOH/DCM to afford Int-7 (0.6 g, 13.6%) as solid. Mass (m/z): 361.2 [M++1]. 1H NMR (500 MHz, dmso-d6): delta 10.76 (brs, 1H), 8.97 (s, 2H), 8.56 (d, J=7, 1H), 8.47 (d, J=5.5 Hz, 1H), 8.38 (s, 1H), 7.58 (d, J=9.5 Hz 1H), 7.34-7.29 (m, 2H), 6.99 (t, J=76 Hz, 1H), 3.84 (s, 3H), 2.46 (s, 3H). To a stirred solution of Int-7 (0.5 g, 1.38 mmol) in MeOH-CH3CN (1:2, 25 mL) was added aqueous NH2OH solution (15 mL) at 0 C. After being stirred for 20 minutes at the same temperature, NaOH (0.44 g, 11.10 mmol) in water (1 mL) was added drop wise to the reaction mixture at 0 C. The reaction mixture was warmed to room temperature and stirred for 2 days. The volatiles were concentrated under vacuum and the obtained residue was diluted with water and neutralized to about pH 7 with 2 N HCl at 0 C. The precipitated solids were filtered off, washed with water (2¡Á10 mL) and dried under vacuum to afford the title compound (0.4 g, 80%) as off-white solid. Mass (m/z): 362.1 [M++1]. 1H NMR (200 MHz, dmso-d6): delta 11.2 (bs, 1H), 10.5 (s, 1H), 9.12 (bs, 1H), 8.84 (s, 2H), 8.57 (d, J=7.0 Hz, 1H), 8.45 (d, J=5.0 Hz, 1H), 8.38 (s, 1H), 7.58 (d, J=9.0 Hz, 1H), 7.32 (t, J=7.5 Hz, 1H), 7.25 (d, J=4.0 Hz, 1H), 6.98 (d, J=7.0 Hz, 1H), 2.49 (s, 3H). 13C NMR (125 MHz, dmso-d6): delta 160.7, 157.1, 153.0, 148.7, 144.5, 142.3, 137.9, 125.2, 123.9, 118.8, 118.2, 117.0, 116.6, 112.7, 112.4, 14.3.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,7752-82-1, 5-Bromopyrimidin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; Melvin, JR., Lawrence S.; Graupe, Michael; Venkataramani, Chandrasekar; US2010/29638; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 4595-59-9, 5-Bromopyrimidine, 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, 4595-59-9, blongs to pyrimidines compound. 4595-59-9

Argon is bubbled for 15 minutes into a mixture of 9.3 g of tert-butyl 1-piperazinecarboxylate, 7.95 g of 5-bromopyrimidine and 6.5 g of sodium tert-butoxide in 250 ml of toluene, which is then heated at reflux, 0.277 g of palladium acetate and 1.7 ml of tri-tert-butylphosphine are added and reflux is continued for 24 hours. 0.277 g of palladium acetate is added and the mixture is heated at reflux for 8 hours. The reaction mixture is cooled to AT, water is added, the mixture is subjected to extraction with AcOEt, the organic phase is filtered and dried over Na2SO4 and the solvent is evaporated under vacuum. The residue is chromatographed on silica gel, eluting with DCM, then with a DCM/AcOEt (50/50; v/v) mixture and finally with a DCM/MeOH (95/5; v/v) mixture. This gives 3.95 g of the expected product following recrystallization from a DCM/hexane/iso ether mixture.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4595-59-9, its application will become more common.

Reference:
Patent; sanofi-aventis; US2005/176722; (2005); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia