Tag: M.W:200-300

137281-39-1, 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. 137281-39-1, name is 4-(2-(2-Amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl)benzoic acid. A new synthetic method of this compound is introduced below.

Example -1: Preparation of Pemetrexed Dimethyl ester of Formula V (R=methyl)4-(2-(2-amino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl)benzoic acid (lOg, 0.034 moles) and N,N-dimethylformamide (50 mL) were stirred for 10-15 minutes under nitrogen atmosphere at room temperature and the reaction mass was cooled to 0 – 5C. 1 -Hydroxybenzotriazole (4.53g) and l-Ethyl-3-(3-dimethylaminopropyl)carbodiimide (6.43) was added at 0 -5C and the reaction mass was maintained for 1-2 hours at 0 – 5C. Then L- glutamic acid dimethyl ester Hydrochloride (8.50g, 0.040 moles) and Diisopropyl ethylamine (4.34g) was then added to reaction mass at 0-5C and the temperature was raised to room temperature. The reaction mass was stirred at room temperature for 2-3 hours and DM Water (500ml) was added. The reaction mass was stirred at room temperature for 10-15 hours. The product was thus filtered under vacuum was crystallized with methanol: acetone mixture and Methanol and Dichloromethane mixture. The product was dried under vacuum oven at 50- 55C for 10-15 hours. Yield (w/w) : 12.5gYield (%) : 80.4%Purity : 98.0%

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. 137281-39-1, 4-(2-(2-Amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl)benzoic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FRESENIUS KABI ONCOLOGY LTD.; SINGH, Govind; GIRIGANI, Sathyanarayana; KUMAR, Sruzen, Suneel; LAHIRI, Saswata; BUBEY, Sushil, Kumar; WO2012/56285; (2012); A1;,
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 130049-82-0, name is 3-(2-Chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidine-4-one. This compound has unique chemical properties. The synthetic route is as follows. 130049-82-0

Example 2 Step-I: Preparation of Crude Paliperidone3-(2-Chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]-pyrimidin-4-one (25 g) was added to ethanol (500 ml) at 25-30 C. under stirring. 6-Fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (20.1 g) and anhydrous sodium carbonate (38 g) were added to the above solution and then heated to 58-62 C. The resulting mass was stirred for 24 hours at 58-62 C. The reaction mass was cooled to 25 C., the inorganic material was filtered out and the resulting mass was washed with ethanol (75 ml). The ethanol was distilled under vacuum in water bath at 50 C. and the resulting residue was dissolved in methylene dichloride (1250 ml). The methylene chloride solution was washed with water (600 ml) 3 times and then dried with anhydrous sodium sulfate. Sodium sulfate was filtered and methylene dichloride was distilled under vacuum at 30-40 C. After complete distillation of methylene chloride, methanol (75 ml) was added to the residue, stirred for 2 hours, filtered the material and dried at 50 C. under high vacuum to yield 23.0 g of crude paliperidone (HPLC Purity: 95.11%; content of the keto impurity: 0.24 wt %).Step-II: Purification of PaliperidoneCrude paliperidone (23 g, obtained in step-I) was heated with dimethylformamide (115 ml) under stirring at 56 C. for 3 hours. The resulting mass was cooled to 25 C., and material was filtered and washed initially with dimethylformamide (23 ml) followed by methanol (23 ml). The resulting solid was heated to 56 C. with dimethylformamide (69 ml) and the mass was stirred for 3 hours and then cooled to 25 C. The resulting mass was filtered and washed initially with dimethylformamide (23 ml) followed by methanol (23 ml). The resulting solid was stirred with methanol (80 ml) for 3 hours, filtered, washed with methanol (80 ml), and then dried in an air oven at 25 C. for 3 hours to yield 13.6 g of paliperidone. The product was then dissolved in methanol (816 ml) at 65 C. to provide a clear solution and the solution was cooled to 50 C. This procedure was followed by the addition of activated carbon (3.5 gm). The resulting mass was stirred for 30 minutes at 50 C. and then filtered on a Hiflo bed. Sodium borohydride (10 mg) was added to the resulting solution and then stirred for 2 hours at 50 C. followed by distillation of methanol until the paliperidone crystallized out. The resulting solution was cooled to 25 C., filtered the material, washed with methanol and then dried at 60 C. under vacuum to yield 10.7 g of pure paliperidone (HPLC Purity: 99.95%; Content of the keto impurity: 0.035 wt %).; Example 4 Purification of PaliperidoneCrude paliperidone (20 g, obtained in step-I of example 2) was heated with sulfolane (100 ml) under stirring at 60 C. for 3 hours, the resulting mass was cooled to 25 C. The material was filtered and washed initially with sulfolane (20 ml) followed by methanol (20 ml). The filtered solid was slurried with sulfolane (60 ml), the resulting slurry was heated to 60 C. under stirring and then maintained for 3 hours. The resulting mass was cooled to 25 C., filtered the solid and washed initially with sulfolane (20 ml) followed by methanol (20 ml). The filtered solid was stirred with water (200 ml) for 1 hour and then the material was filtered and washed with water (100 ml) followed by methanol (50 ml). The resulting solid was then stirred with methanol (100 ml) for 1 hour, and the material was filtered and washed with methanol (50 ml) and then dried in an air oven at 25 C. for 3 hours to yield 13.3 g of paliperidone. The product was then dissolved in methanol (800 ml) at 65 C. to provide a clear solution. The solution was cooled to 50 C. followed by the addition of silica gel (20 g) with stirring for 30 minutes at 50 C. The resulting solution was filtered to remove the silica gel. Sodium borohydride (10 mg) was added to the resulting filtrate and the temperature was maintained for 2 hours at 50 C. Methanol was distilled until paliperidone crystallized out and the resulting solution was cooled to 25 C. The separated solid was filtered, washed with methanol and then dried at 60 C. under vacuum to yield 11 g of pure paliperidone (HPLC Purity 99.7%; Content of the keto impurity at 0.96 RRT: 0.02 wt %).

Statistics shows that 130049-82-0 is playing an increasingly important role. we look forward to future research findings about 3-(2-Chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidine-4-one.

Reference:
Patent; ACTAVIS GROUP PTC EHF; US2009/247553; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

720-01-4, 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.720-01-4, name is Ethyl 4-chloro-2-trifluoromethylpyrimidine-5-carboxylate, molecular formula is C8H6ClF3N2O2, molecular weight is 254.59, as common compound, the synthetic route is as follows.

To a solution of ethyl 4-chloro-2-(trifluoromethyl)pyrimidine-5-carboxylate(30.2 g, 1 19.0 mmol) in ethanol (594 mL) under nitrogen were added palladium (10% on carbon, 50% water wet; 2.58g, 1.21 mmol) and diisopropylethylamine (50.0 mL, 286.0 mmol). The mixture stirred68 under hydrogen (1 atm). After 6 h, the mixture was filtered with Celite. The filtrate was concentrated and ethyl acetate was added. The mixture was washed with sat. NaHCO3 (2x), brine, dried over Na2SO4, filtered and concentrated to give the title compound (25.6 g). MS 221.1 (M+l ).

Statistics shows that 720-01-4 is playing an increasingly important role. we look forward to future research findings about Ethyl 4-chloro-2-trifluoromethylpyrimidine-5-carboxylate.

Reference:
Patent; MERCK SHARP &; DOHME CORP.; BURGEY, Christopher, S.; DENG, Zhengwu, J.; NGUYEN, Diem, N.; PAONE, Daniel, V.; POTTEIGER, Craig, M.; STAUFFER, Shaun, R.; SEGERDELL, Carolyn; NOMLAND, Ashley; LIM, John, J.; WO2010/111058; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

A common compound: 720-01-4, name is Ethyl 4-chloro-2-trifluoromethylpyrimidine-5-carboxylate,molecular formula is C8H6ClF3N2O2, 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., 720-01-4

Example 18 ETHYL 4-HYDRAZINO-2-TRIFLUOROMETHYLPYRIMIDINE-5-CARBOXYLATE A solution of ethyl 4-chloro-2-trifluoromethylpyrimidine-5-carboxylate (0.20 g, 0.79 mmol), hydrazine (0.18 g, 6.0 mmol) and THF was stirred for 1 h at room temperature. The solution was filtered and dried to give the title compound in a 96% yield; 1 H NMR (CDCl3) delta 9.26 (bs, 1H), 8.90 (s, 1H), 4.40 (q, 2H), 4.24 (bs, 2H), 1.41 (t,3H).

With the rapid development of chemical substances, we look forward to future research findings about 720-01-4.

Reference:
Patent; Signal Pharmaceuticals, Inc.; US5935966; (1999); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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.113583-35-0, name is 2-Methanesulfonyl-4,6-dimethoxypyrimidine, molecular formula is C7H10N2O4S, molecular weight is 218.23, as common compound, the synthetic route is as follows.113583-35-0

0.48 g (2.66 mmol) of 2-mercapto-5-fluorobenzoic acid was added.2-methanesulfonyl-4,6-dimethoxypyrimidine 0.87g(4.0 mmol), 0.1 g (0.3 mmol) of tetrabutylammonium bromide in 95% ethanol,The reaction was refluxed for 15 h, and the pH was measured every two hours.Adjust the pH with a saturated aqueous solution of NaHCO3,The pH of the reaction system was maintained at 7 or higher.Post-reaction treatment: spin the reaction system,Extracted three times with NaOH aqueous solution and ethyl acetate,Extract the water layer and adjust the pH to 3-4 with HCl.At this point the aqueous solution turned into a milky white suspension.The aqueous layer was then extracted with ethyl acetate.Add silica gel and spin over the column.The column was passed through a 80:1 (dichloromethane:methanol) eluent.The product was obtained in 0.15 g.The yield was 18%.

Statistics shows that 113583-35-0 is playing an increasingly important role. we look forward to future research findings about 2-Methanesulfonyl-4,6-dimethoxypyrimidine.

Reference:
Patent; Nankai University; Wang Jianguo; Song Guoqing; Wu Renjun; (25 pag.)CN109111405; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

171887-03-9 , The common heterocyclic compound, 171887-03-9, name is N-(2-Amino-4,6-dichloropyrimidine-5-yl)formamide, molecular formula is C5H4Cl2N4O, 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.

5.7 mmol) and DIPEA (2.6 mL; 15.2 mmol) were added to a solutionof 3-amino-1-trityloxymethylphospholane 1-oxide 15 (1.5 g;3.8 mmol) in n-butanol (50 mL). The reaction mixture was stirredfor 40 h at 130 C and evaporated. 3-(2-Amino-6-chloropurine-9-yl)-1-trityloxymethylphospholane 1-oxide 23 was purified bychromatography on silica gel (first isocraticwash with 50% acetone/toluene, second elution with gradient of 0e10% ethanol in chloroform).ESI-MS calcd for C29H28ClN5O2P (M H) 544.2, 546.2 found544.1, 546.1.

According to the analysis of related databases, 171887-03-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Pav, Ond?ej; Bud??insky, Milo?; Rosenberg, Ivan; Tetrahedron; vol. 73; 34; (2017); p. 5220 – 5228;,
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. 130049-82-0, name is 3-(2-Chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidine-4-one, the common compound, a new synthetic route is introduced below. 130049-82-0

Example 4; Preparation of Crude Paliperidone Using N,N-Dimethyl Amino Pyridine (DMAP)A 100 ml Flask equipped with a mechanical stirrer, reflux condenser was charged with CMHTP (7.15 gm), FBIP.HCl (5 gm), diisopropyl ethyl amine (6.5 gm), 4-N,N-dimethyl amino pyridine (0.125 gm) and methanol (50 ml) and stirred at room temperature. The reaction mixture was then refluxed at 60-70 C. for 8 to 10 hr. After completion of the reaction the reaction mixture was cooled to 0 C. and the product obtained was filtered and suck dried. The wet product was dried under vacuum at 50-55 C.Crude Paliperidone: 99.7%N-Oxide Impurity: 0.06%Carboxylate impurity: Not detected

Statistics shows that 130049-82-0 is playing an increasingly important role. we look forward to future research findings about 3-(2-Chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidine-4-one.

Reference:
Patent; ORCHID CHEMICALS & PHARMACEUTICALS LTD.; US2012/165527; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

720-01-4, 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. 720-01-4, name is Ethyl 4-chloro-2-trifluoromethylpyrimidine-5-carboxylate, molecular formula is C8H6ClF3N2O2, 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.

To a solution of ethyl-4-chloro-2-(trifluoromethyl)pyrimidin-5-carboxylate (24) (510 mg, 2.0 mmol) in DCM (10 ml_) at 0C was added diisobutylaluminum hydride (1 M solution in toluene) (6.0 ml_, 6.0 mmol). The mixture was slowly allowed to warm to room temperature and was stirred overnight. The reaction mixture was quenched with sat. aq. Rochelle’s salt and stirred for 30 min before concentrating down the solution. The product was then extracted into EtOAc (3 x 30 ml_) and the combined organic layers were washed with brine (50 ml_), dried (MgS04) and solvent evaporated to leave a clear oil. The crude was purified by column chromatography (S1O2, 10 g, gradient elution 10% EtOAc in petrol to 50% EtOAc in petrol). The desired fractions were concentrated under reduced pressure to afford the title compound as a yellow oil (96 mg, 23%); 1H NMR (500 MHz, Chloroform- d) d 9.01 (s, 1 H), 4.92 (s, 2H); LCMS (4 minute method) product at Rt = 0.44 min and ES+ m/z the desired mass ion was not observed.

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. 720-01-4, Ethyl 4-chloro-2-trifluoromethylpyrimidine-5-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE UNIVERSITY OF SUSSEX; CARDIFF UNIVERSITY; UNIVERSITY COLLEGE CARDIFF CONSULTANTS LIMITED; WARD, Simon; BESWICK, Paul; PENNICOTT, Lewis; REUILLON, Tristan; CHUCKOWREE, Irina; VILLALONGA-BARBER, Carolina; PORTER, Roderick, Alan; (120 pag.)WO2019/166822; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 3740-92-9

3.77g ((4-(5H-benzofuro[3,2-c]carbazol-5-yl)phenyl)boronic acid) (10mmol, 1eq) with 9g (22mmol, 4eq)4,6-Dichloro-2phenylpyrimidine, N2 was exchanged three times, and 0.16 g (0.1 mmol, 1percent eq) of tetrakistriphenylphosphine palladium was added under the protection of N2.2M K2CO3 aqueous solution, ethanol, toluene (volume ratio = 1:2:1), a total of 100ml in an anaerobic environment for 12h,The ethanol and toluene were distilled off under reduced pressure, dissolved in dichloromethane, and the organic phase was washed with water.The filtrate was subjected to column chromatography to obtain 3.12 g of (5-(4-(6-chloro-2-phenylpyrimidin-4-yl)phenyl)-5H-benzofuro[3,2-c]carbazole) (60percent);

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; Huazhong University of Science and Technology; Wang Lei; Zhang Qing; Zhuang Shaoqing; (40 pag.)CN108285452; (2018); A;,
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. 113583-35-0, name is 2-Methanesulfonyl-4,6-dimethoxypyrimidine, molecular formula is C7H10N2O4S, 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. 113583-35-0

Example 3 Methyl 2-(4,6-dimethoxy-pyrimidin-2-yloxy)-3-methoxy-3,3-diphenylpropionate 2.86 g (10 mmol) of methyl 2-hydroxy-3-methoxy-3,3-diphenylpropionate were dissolved in 40 ml of dimethylformamide, and 0.3 g (12 mmol) of sodium hydride was added. The mixture was stirred for 1 h and then 2.2 g (10 mmol) of 4,6-dimethoxy-2-methylsulfonylpyrimidine were added. After stirring at room temperature for 24 h, cautious hydrolysis was carried out with 10 ml of water, the pH was adjusted to 5 with acetic acid, and the solvent was removed by distillation under high vacuum. The residue was taken up in 100 ml of ethyl acetate, washed with water and dried over magnesium sulfate, and the solvent was distilled out. The residue was mixed with 10 ml of ether, and the resulting precipitate was filtered off with suction. After drying, 3.48 g (82%) of a white powder remained. Melting point 81 C.

The chemical industry reduces the impact on the environment during synthesis 113583-35-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; BASF Aktiengesellschaft; US5932730; (1999); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia