Tag: M.W=300-400

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.761440-16-8, name is 2,5-Dichloro-N-(2-(isopropylsulfonyl)phenyl)pyrimidin-4-amine, molecular formula is C13H13Cl2N3O2S, molecular weight is 346.23, as common compound, the synthetic route is as follows.HPLC of Formula: C13H13Cl2N3O2S

2,5-dichloro-N-(2-(isopropylsulfonyl)phenyl)py-rimidine-4-amine (472 mg, i.36 mmol) was dissolved in 0.08 M HC1-ethoxyethanol (i .0 mE), to which the compound (200 mg, 0.979 mmol) prepared in preparative example 2i was added, followed by stirring at 80 C. for i2 hours. The reaction mixture was cooled to room temperature, neutralized with sodium hydrogen carbonate aqueous solution, and extracted twice with ethylacetate. The extracted organic layer was dried over sodium sulfate and then filtered. The solvent was eliminated by distillation under reduced pressure. Then, purification was performed by silica gel column chromatography (eluent: methanol dichloromethane, 1/9) to give the target compound 2-(4-((5- chioro-4-((2-(isopropylsulfonyl)phenyl)amino)pyrimidine- 2-yl)amino)-5-methoxy-2-methylphenyl)-2- methylpropanenitrile as a white solid (433 mg, 0.875 mmol, yield: 86%).10584] ?H-NMR (300 MHz, CDC13) oe 9.53 (s, br, 1H),8.52 (d, J=8.3 Hz, 1H), 8.18 (s, 1H), 8.12 (s, 1H), 7.94 (d,J=7.9 Hz, 1H), 7.66 (t, J=7.3 Hz, 1H), 7.53 (s, br, 1H), 7.28(t, J=7.8 Hz, 1H), 6.83 (s, 1H), 3.90 (s, 3H), 3.26 (sept, J=6.9Hz, 1H), 2.44 (s, 3H), 1.79 (s, 6H), 1.32 (d, J=6.9 Hz, 6H);LC/MS 513.8 [M+H].

At the same time, in my other blogs, there are other synthetic methods of this type of compound,761440-16-8, 2,5-Dichloro-N-(2-(isopropylsulfonyl)phenyl)pyrimidin-4-amine, and friends who are interested can also refer to it.

Reference:
Patent; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; Kim, Pilho; Kim, Hyoung Rae; Cho, Sung Yun; Ha, Jae Du; Jung, Hee Jung; Yun, Chang Soo; Hwang, Jong Yeon; Park, Chi Hoon; Lee, Chong Ock; Ahn, Sunjoo; Chae, Chong Hak; (97 pag.)US2018/111905; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 153435-63-3 ,Some common heterocyclic compound, 153435-63-3, molecular formula is C16H30N2Sn, 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.

Step 1: methyl 1-methyl-4-(pyrimidin-2-yl)-1H-pyrazole-3-carboxylate A mixture of methyl 4-bromo-1-methyl-1H-pyrazole-3-carboxylate (1.5 g, 6.84 mmol, 1.0 eq), 2-(tributylstannyl)pyrimidine (2.4 mL, 7.52 mmol, 1.1 eq), CsF (2.1 g, 13.67 mmol, 2.0 eq), Pd(PPh3)4 (0.79 g, 0.68 mmol, 0.1 eq) and CuI (0.13 g, 0.68 mmol, 0.1 eq) in DMF (120 mL) was degassed for 10 min and then heated overnight at oil bath at 110C. The completion of the reaction was monitored by analytical HPLC. When complete, the mixture was cooled and concentrated. The crude was dissolved with EtOAc and washed with Sat’d NaHCO3 and brine. The solvent was removed to obtain the crude, which was purified by silica gel to obtain the desired product. ESI-MS (m/z): 218.99 [M+1]+.

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. 153435-63-3, 2-(Tributylstannyl)pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; EOLAS THERAPEUTICS, INC.; KAMENECKA, Theodore, M.; HOLENZ, Joerg; WESOLOWSKI, Steven; HE, Yuanjun; BUeRLI, Roland; (201 pag.)WO2017/139603; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 1109284-33-4, 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 1109284-33-4, name is 6-Bromo-3-iodopyrazolo[1,5-a]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

In the flask, 3-iodo-6-bromopyrazolo[1,5-a]pyrimidine (1 g, 3.1 mmol) was added.4-diphenylaminophenylboronic acid (1.8 g, 6.2 mmol),Potassium carbonate (0.86g, 6.2mmol),Tetrakistriphenylphosphine palladium (50mg),Tetrahydrofuran (20 mL) and water (10 mL),Under the protection of nitrogen,Heated for 12 hours,cool down,Extracted with dichloromethane,dry,concentrate,The crude product was purified by column chromatography to yield 1.59 g of product.

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 1109284-33-4, 6-Bromo-3-iodopyrazolo[1,5-a]pyrimidine.

Reference:
Patent; Shanghai Daoyi Chemical Technology Co., Ltd.; Huang Jinhai; Su Jianhua; (18 pag.)CN108484608; (2018); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 302964-08-5, Adding some certain compound to certain chemical reactions, such as: 302964-08-5, name is 2-((6-Chloro-2-methylpyrimidin-4-yl)amino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide,molecular formula is C16H13Cl2N5OS, 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 302964-08-5.

General Procedure A. To a suspension of thiazole-carboxamide 44 (1.0 eq, prepared as outlined in McIntyre, J A et al., Drugs of the Future, 2006, 31(4): 291) in 1,4-dioxane (10 mL/1 mmol) at rt was added diisopropylethylamine (DIPEA, 5.0 eq) followed by the piperazine 45-d4 (1.5 eq to 5.0 eq; generally 1.5 eq of the piperazine analogue was enough to achieve the complete displacement with extended reaction time). The reaction mixture was stirred under reflux conditions until no starting material was detectable (24-72 h), was stripped of solvent in vacuo, then dry-loaded onto a silica-gel column with 94:5:1 CH2Cl2/MeOH/ammonium hydroxide as eluent to give the desired product in 96 to >99% purity. Occasionally, residual solvents, detected by 1H-NMR, were removed by co-evaporation with water. Compound 100: 1H-NMR (300 MHz, DMSO-d6): delta 2.24 (s, 3H), 2.41 (s, 3H), 2.48-2.51 (m, 4H, obscured by DMSO peak), 3.51 (bs, 4H), 4.42 (s, 1H), 6.05 (s, 1H), 7.23-7.31 (m, 2H), 7.41 (dd, J1=7.3, J2=2.0, 1H), 8.22 (s, 1H), 9.90 (s, 1H), 11.50 (s, 1H). 13C-NMR (75 MHz, DMSO-d6): delta 18.20, 25.49, 43.48, 52.57, 82.48, 125.57, 126.92, 128.08, 128.94, 132.32, 133.40, 138.71, 140.71, 156.80, 159.80, 162.26, 162.44, 165.05. HPLC (method: 20 mm C18-RP column-gradient method 2-95% ACN+0.1% formic acid in 3.3 min with 1.7 min hold at 95% ACN; Wavelength: 254 nm): retention time: 2.57 min. MS (M+H): 492.0. Elemental Analysis (C22H22D4ClN7O2S.0.25H2O): Calculated: C=53.22; H=5.38; Cl=7.14; N=19.75; S=

According to the analysis of related databases, 302964-08-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CONCERT PHARMACEUTICALS INC.; US2009/149399; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 428854-24-4, 2-(1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl)pyrimidine-4,5,6-triamine, 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, name: 2-(1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl)pyrimidine-4,5,6-triamine, blongs to pyrimidines compound. name: 2-(1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl)pyrimidine-4,5,6-triamine

B, to 500 ml reaction vial the adding step a 29.0g (0.083mol) compound 3,150 ml methanol, 9.7g (0.1mol) carbonic acid dimethyl ester (compound 4), in 30 C stirring reaction under 6h; after the reaction, the obtained reaction solution in the 50 C, vacuum 0.09 MPa reducing pressure and evaporating the solvent, the residue obtained by adding 150 ml ethyl acetate stirring 15 min, filter, the filtration cake at the 65 C, vacuum 0.09 MPa dry the 5h, to obtain 4,6-diamino-2 – [1 – (2-fluorobenzyl) – 1H-pyrazolo [3,4-b] pyridin-3-yl] – 5-pyrimidinyl amino a acid methyl ester (compound 5) 29.8g (yield 88%);

The synthetic route of 428854-24-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Drug Technology Co., Ltd.; Mao, Ying; Bi, Tianhao; Li, Jinhua; Liu, Zhiqing; Lou, Lili; Zhang, Jiamei; (11 pag.)CN105294686; (2016); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 374930-88-8, Adding some certain compound to certain chemical reactions, such as: 374930-88-8, name is tert-Butyl 4-(5-bromopyrimidin-2-yl)piperazine-1-carboxylate,molecular formula is C13H19BrN4O2, 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 374930-88-8.

Synthesis of tert-butyl 4-(5-acetylpyrimidin-2-yl)piperazine-1-carboxylate To a mixture of tert-butyl 4-(5-bromopyrimidin-2-yl)piperazine-1-carboxylate (5.0 g, 14.6 mmol), palladium diacetate (240 mg, 1.46 mmol) and triphenylphosphine (376 mg, 2.92 mmol) in dioxane (100 mL) was added tributyl(1-ethoxyvinyl)stannane (5.3 mL, 16.1 mL) under N2, and the reaction mixture was stirred at 80 C. overnight. The reaction was cooled to RT and diluted with THF (100 mL), followed by the addition of 2 N HCl (100 mL). The mixture was stirred at RT for 30 mins, and LCMS showed the reaction was completed. The reaction mixture was diluted with ethyl acetate (200 mL). The organic phase was separated, washed with water (3*100 mL), dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel column chromatography to afford the title compound (3.0 g, 67%). MS (ES+) C15H22N4O3 requires: 306, found: 251 [M-56+H]+.

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. 374930-88-8, tert-Butyl 4-(5-bromopyrimidin-2-yl)piperazine-1-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BLUEPRINT MEDICINES CORPORATION; Hodous, Brian L.; Kim, Joseph L.; Miduturu, Chandrasekhar V.; Wilson, Douglas; Zhang, Yulian; US2015/111857; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 1111638-74-4 ,Some common heterocyclic compound, 1111638-74-4, molecular formula is C8H7IN4S, 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: 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.

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. 1111638-74-4, 4-(3-Iodo-1H-pyrazol-4-yl)-2-(methylthio)pyrimidine, other downstream synthetic routes, hurry up and to see.

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

Reference of 330786-24-8 ,Some common heterocyclic compound, 330786-24-8, molecular formula is C17H13N5O, 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.

6) Add IM6 (4.5 g, 0.015 mol) in sequence to a 250 mL three-necked flask. N-Boc Hydroxylpiperazine (3.6 g, 0.018 mol), Triphenylphosphine (7.9 g, 0.03 mol) and tetrahydrofuran (45 mL) were cooled in an ice bath. DIAD (6.1 g, 0.03 mol) was added dropwise with stirring. The temperature was controlled to not exceed 20 degrees Celsius. After the addition was complete, the mixture was stirred at room temperature for about 5 hours. Add 45 mL concentrated hydrochloric acid to the reaction flask and stir at room temperature for about 5 h. The tetrahydrofuran was concentrated and removed, poured into 150 mL of water and washed with dichloromethane. The aqueous layer was adjusted to neutral pH with potassium carbonate and extracted with dichloromethane. The organic layers were combined, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated to give IM7 (4.0 g , 69%).

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; Nanjing Yi Hua Pharmaceutical Co., Ltd.; Yuan Jing; Liu Wu; Zhang Xia; (7 pag.)CN107641123; (2018); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 862730-04-9, 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. 862730-04-9, name is 3-Iodo-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine. A new synthetic method of this compound is introduced below.

Synthesis of 3-(4-amino-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-N-(4,5-dihydrothiazol-2-yl)benzamide (BA30); A solution of [3-((4,5-dihydrothiazol-2-yl)carbamoyl)phenyl]boronic acid (19 mg, 0.08 mmol) in EtOH (3.3 ml) was added to a solution of 3-iodo-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine (20 mg, 0.07 mmol) in DME (12 ml). Pd(PPh3)4 (16 mg, 0.014 mmol) and saturated Na2CO3 (1.9 ml) were added and the reaction was heated to 80 C. under an argon atmosphere overnight. After cooling, the reaction was extracted with saturated NaCl and CH2Cl2. Organic phases were combined, concentrated in vacuo and purified by RP-HPLC (MeCN:H2O:0.1% TFA) to yield BA30 (17.8 mg, 67% yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,862730-04-9, 3-Iodo-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine, and friends who are interested can also refer to it.

Reference:
Patent; Regents of the University of California; US2007/293516; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 1111638-74-4 ,Some common heterocyclic compound, 1111638-74-4, molecular formula is C8H7IN4S, 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: 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.

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. 1111638-74-4, 4-(3-Iodo-1H-pyrazol-4-yl)-2-(methylthio)pyrimidine, other downstream synthetic routes, hurry up and to see.

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