Month: February 2021

Synthetic Route of 89793-12-4 ,Some common heterocyclic compound, 89793-12-4, molecular formula is C7H7ClN2O2, 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 solution of compound 5 (9.6 g, 26 mmol), 2-Cl-pyrimidine (4.9 g, 26 mmol) in 150 ml 1 ,4-Dioxane was added DIPEA (7.7 g, 60 mmol). The mixture was stirred at 110¡ã C. overnight. ECMS was used to monitor the reaction to completion. Water (50 ml) was added and the mixture was extracted with EtOAc. The combined organic extracts were washed and dried. The target compound 6 (11 g, 90percent) was purified by flash chromatography with PE/EA from 30:1 to2:1.

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. 89793-12-4, Ethyl 2-chloropyrimidine-5-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Acetylon Pharmaceuticals, Inc.; Jones, Simon Stewart; Yang, Min; Tamang, David Lee; US2015/105384; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 22536-61-4, 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. 22536-61-4, name is 2-Chloro-5-methylpyrimidine, molecular formula is C5H5ClN2, 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.

0.40 g of 2-chloro-5-methylpyrimidine was dissolved in 15 ml of carbontetrachloride and then added with 0.83 g of N-bromosuccinimide and 0.05 g of azobisisobutyronitrile, followed by heating under reflux for 8 hours. The reaction mixture was cooled down to room temperature and then filtrated, followed by the filtrate being concentrated under reduced pressure. The residue was subjected to a silica gel column chromatography to obtain 0.27 g of 5-bromomethyl-2-chloropyrimidine represented by above formula.1H-NMR (CDCl3, TMS) , delta (ppm) : 4.43 (2H, s), 8.67 (2H, s)

According to the analysis of related databases, 22536-61-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sumitomo Chemical Company, Limited; EP1555259; (2005); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 137234-74-3, 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. 137234-74-3, name is 4-Chloro-6-ethyl-5-fluoropyrimidine. A new synthetic method of this compound is introduced below.

PREPARATION EXAMPLE 19: Preparation of 4-(1-Bromoethyl)-6-chloro-5-fluoropyrimidine A solution of 5 g of 6-chloro-4-ethyl-5-fluoropyrimidine, 6.65 g of NBS, and 0.51 g of AIBN in 50 ml of methylene chloride was stirred for 12 hrs under reflux. The reaction was cooled to room temperature and added with 30 ml of pure water. The organic layer was obtained, and the aqueous fraction was extracted with 30 ml of methylene chloride. The organic layers thus obtained were pooled and washed with 30 ml of 10 % sodium metabisulfite, and then with pure water. After dehydration with a desiccant, the obtained product was concentrated under reduced pressure to afford 6.95 g of the title compound (Yield: 95.1%). 1H NMR (CDCl3) delta 8.80(s, 1H), 5.35(q, 1H), 2.08(d, 3H) ppm

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,137234-74-3, its application will become more common.

Reference:
Patent; Boryung Pharmaceutical Co., Ltd.; KIM, Ji Han; KIM, Je Hak; LEE, Joon Kwang; JUNG, Hahn-Sun; HAN, Nam Seok; PARK, Yong; KANG, Seung-Hoon; JEONG, Hee Jin; LEE, Kyung-Tae; CHOI, Hye Eun; CHI, Yong Ha; LEE, Joo Han; PAIK, Soo Heui; EP2754655; (2014); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 4433-40-3, name is 5-(Hydroxymethyl)pyrimidine-2,4(1H,3H)-dione, the common compound, a new synthetic route is introduced below. Quality Control of 5-(Hydroxymethyl)pyrimidine-2,4(1H,3H)-dione

To a suspension of 5-(hydroxymethyl)pyrimidine-2,4(1H,3H)-dione (35.0 g, 246.3 mmol) in toluene (100 mL) was added POCl3 (105 mL, 1147 mmol) followed by slow addition of DIPEA (120 mL, 689 mmol), the mixture was tirred at 110-120 oC for 8 h. Then the reaction mixture was poured to a mixture of water (100 mL) and ethyl acetate (200 mL), extracted with ethyl acetate (1 L ¡Á 2), washed with brine (200 mL ¡Á 3), died with Na2SO4. Purified by silica gel (DCM) to give 2,4-dichloro-5- (chloromethyl)pyrimidine as light yellow solid (22 g), yield 46percent. LC/MS (ESI) m/z = 197 (M + H) +.

The synthetic route of 4433-40-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE BROAD INSTITUTE, INC.; DANA-FARBER CANCER INSTITUTE, INC.; THE GENERAL HOSPITAL CORPORATION D/B/A MASSACHUSETTS GENERAL HOSPITAL; GRAY, Nathanael, S.; LIANG, Yanke; CHOI, Hwan, Geun; SUNDBERG, Thomas; SHAMJI, Alykhan; XAVIER, Ramnik; FISHER, David E.; (251 pag.)WO2018/9544; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 5750-76-5, 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. 5750-76-5, name is 2,4,5-Trichloropyrimidine. A new synthetic method of this compound is introduced below.

General procedure: A solution of 2,4,5-trichloropyrimidine(1.82 g, 10 mmol), (2-aminophenyl)dimethylphosphine oxide(1.69 g, 10 mmol) and N,N-diisopropylethylamine (1.94 g, 15 mmol)in propan-2-ol (25 mL) was heated under reflux for 12 h. The solvent was removed by evaporation and the residue was dissolvedin CH2Cl2 (100 mL). The solution was washed with water andsaturated sodium chloride solution and dried, filtered andconcentrated. The residuewas purified by flash chromatography onsilica gel (0e2% MeOH in DCM) to afford compound 51l (1.60 g,50%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,5750-76-5, 2,4,5-Trichloropyrimidine, and friends who are interested can also refer to it.

Reference:
Article; Chen, Yongfei; Wu, Jiaxin; Wang, Aoli; Qi, Ziping; Jiang, Taoshan; Chen, Cheng; Zou, Fengming; Hu, Chen; Wang, Wei; Wu, Hong; Hu, Zhenquan; Wang, Wenchao; Wang, Beilei; Wang, Li; Ren, Tao; Zhang, Shanchun; Liu, Qingsong; Liu, Jing; European Journal of Medicinal Chemistry; vol. 139; (2017); p. 674 – 697;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 7033-39-8 ,Some common heterocyclic compound, 7033-39-8, molecular formula is C6H7BrN2O2, 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 mixture of 1,3-dimethyluracil (0.140 g, 1 mmol), CuBr (0.057 g, 0.4 mmol, 0.4 equiv), and the aryl iodide (2 mmol, 2 equiv) in DMF (2 mL) was added LiOtBu (0.320 g, 4 mmol, 4 equiv). The reaction mixture was heated at reflux temperature for 1 h. After cooling to the room temperature, the reaction was quenched by adding saturated aqueous NH4Cl solution.The solvent was removed under reduced pressure. The residue was partitioned between EtOAc and H2O. The organic layer was washed with saturated aqueous NaCl solution, dried over anhydrous MgSO4, and then concentrated under reduced pressure to dryness. The residue was purified by flash column chromatography to give the product.

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. 7033-39-8, 5-Bromo-1,3-dimethylpyrimidine-2,4(1H,3H)-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Cheng, Chien; Shih, Yu-Chiao; Chen, Hui-Ting; Chien, Tun-Cheng; Tetrahedron; vol. 69; 4; (2013); p. 1387 – 1396;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 10457-14-4 ,Some common heterocyclic compound, 10457-14-4, molecular formula is C10H20N2O2Si2, 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.

Compound 8c (703 mg, 1.24 mmol), bis-TMS uracil (630 mg, 2.46 mmol), and silver(I)triflate (630 mg, 2.46 mmol) were placed into a microwave vial under argon, and anhydrous dichloroethane (5 mL) and acetonitrile (5 mL) were added. The mixture was heated at 135 C. for 30 minutes via use of a microwave reactor. The reaction mixture was cooled to room temperature, filtered, and the volatiles were removed in vacuo. The crude material was purified via chromatography on silica gel (eluent: hexanes/EtOAc) affording Compound 8d (504 mg, 0.845 mmol) as a single isomer. 1H-NMR (400 MHz, CDCl3): delta 8.08 (d, J=7.2 Hz, 2H), 8.03-8.00 (m, 4H), 7.62-7.37 (m, 10H), 6.36 (d, J=5.6 Hz, 1H), 6.11 (m, 1H), 5.66 (dq, J=7.2/2.8 Hz, 1H), 4.50 (dd, J=8.4/2.4 Hz, 1H), 4.90 (m, 1H), 1.57 (d, J=6.8 Hz, 3H) ppm. MS=596 (M+H+). LC/MS retention time on a 6 minute LC/MS method (Polar RP column)=4.43 min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,10457-14-4, its application will become more common.

Reference:
Patent; GILEAD SCIENCES, INC.; US2012/263678; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 271-70-5, 7H-Pyrrolo[2,3-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, 271-70-5, blongs to pyrimidines compound. category: pyrimidines

General procedure: Procedure C: A solution of 4-methyl-7H-pyrrolo[2,3-d]pyrimidine (1, 0.4 g, 3.0 mmol), 5-bromo-2-(4-methoxybenzyl) isoindolin-1-one (2, 1.0 g, 4.5 mmol) and potassium phosphate (1.91 g, 9.0 mmol) in 1, 4-dioxane (15 ml) was degassed with nitrogen for 10 min. Copper (I) iodide (0.28 g, 1.5 mmol) and trans-1, 2-diaminocyclohexane (0.17 g, 1.5 mmol) were added and the reaction was refluxed at 90 C. for 16 h. Progress of the reaction was monitored by TLC. After completion, solvent was removed under reduced pressure. The reaction mixture was diluted with water and extracted twice with ethyl acetate. The organic layer was separated, dried over sodium sulphate, filtered and concentrated under reduced pressure to afford 2-(4-methoxybenzyl)-5-(4-methyl-7H-pyrrolo [2, 3-d] pyrimidin-7-yl) isoindolin-1-one (3) as a yellow solid. Yield: 0.55 g, 47%;

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,271-70-5, its application will become more common.

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

Adding a certain compound to certain chemical reactions, such as: 74901-69-2, 2,4-Dichloro-6,7-dihydrothieno[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, 74901-69-2, blongs to pyrimidines compound. Quality Control of 2,4-Dichloro-6,7-dihydrothieno[3,2-d]pyrimidine

To a solution of 2,4-dichloro-6,7-dihydrothieno[3,2-d]pyrimidine (2.50 g, 12 mmol) in DMSO (8 mL) was added DIPEA (4.2 mL, 24 mmol) and 6-oxaspiro[3.3]heptan-2- amine hydrochloride (2.00 g, 13 mmol) was added. The reaction mixture was stirred at rt overnight. Water ( 10 mL) was added and the obtained slurry was stirred for 30 min before filtration and subsequent washings with water afforded the title compound as solid material. 1H NMR (DMSO-d6) delta: 7.43 (d, J = 7.1 Hz, 1H), 4.62 (s, 2H), 4.49 (s, 2H), 4.26 (h, J = 8.1 Hz, 1H), 3.39 – 3.31 (m, 2H), 3.17 – 3.08 (m, 2H), 2.62 – 2.53 (m, 2H), 2.30 – 2.16 (m, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,74901-69-2, its application will become more common.

Reference:
Patent; LEO PHARMA A/S; LARSEN, Jens; (110 pag.)WO2019/57806; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 151266-23-8 , The common heterocyclic compound, 151266-23-8, name is 3-Iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine, molecular formula is C5H4IN5, 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 3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine (103) (2.0 g, 7.66 mmol) in anhydrous N,N-dimethylformamide (50 mL) under an argon atmosphere, potassium carbonate (4.23 g, 30.6 mmol) and bromocyclopentane (1.37 g, 9.20 mmol, 1.2 eq) were added sequentially. The resulting mixture was stirred at 80 C. for 5 h and then was allowed to cool to room temperature. The mixture was filtered and the filtrate was concentrated to half volume in vacuo and then partitioned between water and ethyl acetate. The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to afford the desired product, 1-cyclopentyl-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine (601) (1.27 g, 50.4% yield) as a yellow solid. ESI-MS (M+H)+ m/z: 330.1.

The synthetic route of 151266-23-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Intellikine LLC; Ren, Pingda; Liu, Yi; Wilson, Troy Edward; Li, Liansheng; Chan, Katrina; US2015/225407; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia