Tag: M.W:100-200

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

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

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

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

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

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

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 stirred solution of 5-bromopyrimidin-2-amine(A39, 1.0 g, 5.74 mmol) in DMF (20 mL) was added ethyl 3-bromo pyruvate(A15, 0.86 mL, 6.89 mmol) . The reaction mixture was Stirred for 16 h at Room temp and then concentrated under reduced pressure. The crude product was triturated with water and washed with n-pentane and dried to afford ethyl 6-bromoimidazo[l,2-a]pyrimidine-2-carboxylate A40 as light brown solid Yield: 1.50 g,(87%). LC-MS m/z : 268.20[M-H]

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; JUBILANT BIOSYS LIMITED; VADIVELU, Saravanan; RAJAGOPAL, Sridharan; BURRI, Raghunadha Reddy; GARAPATY, Shivani; SIVANANDHAN, Dhanalakshmi; THAKUR, Manish Kumar; NATARAJAN, Tamizharasan; SWAMY, Indu N; NAGARAJU, Nagendra; KANAGARAJ, Subramaniam; MOHD, Zainuddin; SARKAR, Sayantani; SAMANTA, Swapan Kumar; ., Hariprakash; (284 pag.)WO2019/102494; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

7226-23-5, A common compound: 7226-23-5, name is 1,3-Dimethyltetrahydropyrimidin-2(1H)-one,molecular formula is C6H12N2O, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

A solution of diisopropylamine (951 muL, 6.79 mmol) in dry tetrahydrofuran (6 mL) and 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (2 mL) was cooled to -78 C. under nitrogen and then treated with a 2.5M solution of n-butyllithium in hexanes (2.5 mL, 6.79 mmol). The resulting reaction mixture was stirred at -78 C. for 30 min and then treated dropwise with a solution of (3,4-bis-methanesulfonyl-phenyl)-acetic acid methyl ester (1.89 g, 6.17 mmol) in dry tetrahydrofuran (12 mL) and 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (4 mL). The resulting reaction mixture was allowed to stir at -78 C. for 1 h, at which time, a solution of iodomethylcyclopentane (1.56 g, 7.40 mmol) in a small amount of dry tetrahydrofuran was added dropwise. The reaction mixture was allowed to warm to 25 C. where it was stirred for 64 h. The reaction mixture was quenched with water (150 mL) and then concentrated in vacuo to remove tetrahydrofuran. The remaining residue was further diluted with water (100 mL) and then extracted with ethyl acetate (1*250 mL). The organic layer was washed with a saturated aqueous sodium chloride solution (1*100 mL), dried over magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 70-230 mesh, 3/1 hexanes/ethyl acetate) afforded 2-(3,4-bis-methanesulfonyl-phenyl)-3-cyclopentyl-propionic acid methyl ester (1.61 g, 67%) as a yellow oil: EI-HRMS m/e calcd for C17H24O6S2 (M+) 388.1014, found 388.1014.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 7226-23-5.

Reference:
Patent; Bizzarro, Fred Thomas; Corbett, Wendy Lea; Grippo, Joseph Francis; Haynes, Nancy-Ellen; Holland, George William; Kester, Robert Francis; Sarabu, Ramakanth; US2001/39344; (2001); A1;; ; Patent; Hoffman-La Roche Inc.; US6610846; (2003); B1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

2380-63-4, 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 2380-63-4, name is 1H-Pyrazolo[3,4-d]pyrimidin-4-amine. This compound has unique chemical properties. The synthetic route is as follows.

The A10.7g (5.2mmol), bromocyclopentane 1.55g (10.4mmol, 2eq.) And cesium carbonate 3.39g (10.4mmol, 2eq.), In 12mL DMF solution, 110 deg.] C overnight, was concentrated acetic acid ethyl, dried, Biotage silica gel column chromatography (dichloromethane / methanol = 1%) to give a pale yellow solid A90.84g, yield 80%.

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 2380-63-4, 1H-Pyrazolo[3,4-d]pyrimidin-4-amine.

Reference:
Patent; Nanjing Yong Shan Biological Technology Co., Ltd.; Wang Yazhou; Jin Qiu; Tang Feng; Huang Wei; Hua Yulin; (10 pag.)CN103113375; (2017); B;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

1193-24-4, 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 1193-24-4 as follows.

Example 2; To a 1000 mL four-neck flask, 89.7 g of 4,6-dihydroxypyrimidine and 179.3 g of chlorobenzene were added. The obtained mixture was adjusted at 40C, and then, 129.6 g of sulfuryl chloride was added dropwise thereto over 1 hour. The obtained mixture was maintained at the same temperature for 6 hours. To the obtained reaction mixture, 269.9 g of phosphorus oxychloride was added at the same temperature. Further, 178.1 g of triethylamine was added dropwise thereto over 2 hours at an inner temperature of 40 to 80C. After completion of the addition, the obtained mixture was maintained at 83C for 10 hours. The obtained reaction mixture was cooled to room temperature. To another 100 mL four-neck flask, 269.0 g of water was added followed by adjusting at 40C. To it, the obtained reaction mixture was added dropwise over 30 minutes. The inner temperature during the addition was 30 to 50C. The obtained mixture was filtrated using Radiolite (registered trademark) and the obtained filtrate was separated to an organic layer and an aqueous layer. The aqueous layer was extracted with 44.8 g of chlorobenzene, and the obtained chlorobenzene layer was mixed with the previously obtained organic layer. The organic layer after mixing was washed with 44.8 g of water and then, concentrated under reduced pressure to obtain 169.2 g of black oily matter. The oily matter was analyzed by high performance liquid chromatography internal standard method, and 126.9 g of 4,5,6-trichlorpyrimidine was containd in the oily matter. The yield was 86%.

The chemical industry reduces the impact on the environment during synthesis 1193-24-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Sumitomo Chemical Company, Limited; EP2128141; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia