Pyrimidines

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.14080-50-3, name is Thieno[2,3-d]pyrimidin-4(3H)-one, molecular formula is C6H4N2OS, molecular weight is 152.1738, as common compound, the synthetic route is as follows.name: Thieno[2,3-d]pyrimidin-4(3H)-one

Example 307 Synthesis of 4-chlorothieno[2,3-d]pyrimidine DMF (1.53 ml, 19.7 mmol) in dichloromethane (50 ml) was cooled to 0 C. and oxalyl chloride (2.5 ml, 29.6 mmol) was added slowly forming a white gel. Thieno[2,3-d]pyrimidin-4(3H)-one (1.5 g, 9.86 mmol) was added and the reaction mixture was refluxed for 3 hours. The mixture was cooled down to room temperature and poured into water. The mixture was extracted with dichloromethane, dried over sodium sulfate and concentrated in vacuo. The crude residue was purified by silica gel chromatography (EtOAc/hexane 15:1) to yield the title compound as a white solid (1.61 g, 96%). 1H NMR (300 MHz, CDCl3, 25 C.): delta=8.88 (s, 1H, CH), 7.64 (d, J=6.0 Hz, 1H, CH), 7.47 (d, J=5.8 Hz, 1H, CH) ppm. HRMS: calcd for C6H4ClN2S 170.97837. found 170.97804.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,14080-50-3, Thieno[2,3-d]pyrimidin-4(3H)-one, and friends who are interested can also refer to it.

Reference:
Patent; Katholieke Universiteit Leuven, K.U. Leuven R&D; Herman, Jean; Louat, Thierry; US2014/88088; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 24391-41-1, 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 24391-41-1, name is 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 14b (0.132 mmol), 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5- carbonitrile (24 mg, 0.132 mmol) and TEA (0.09 mL, 0.66 mmol) in n-BuOH (10 mL) was heated at reflux for 2 hours. The reaction mixture was concentrated purified by flash column chromatography eluting with MeOH/water to afford compound 107 as a slight yellow solid (17 mg, yield: 31%). MS (m/z): 420.7 (M+H)+. 1H-NMR (400 MHz, DMSO-d6) delta: 8.29 (s, 1H), 8.03 (s, 1H), 6.77 (t, J= 5.1 Hz, 1H), 6.16 (t, J= 4.0 Hz, 1H), 5.50 (m, 1H), 4.26 (m, 1H), 4.15 – 4.08 (m, 2H), 3.69 (m, 1H), 2.37 – 2.01 (m, 5H), 1.00 (d, J= 6.6 Hz, 3H), 0.93 (d, J= 6.5 Hz, 3H).

According to the analysis of related databases, 24391-41-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; HUTCHISON MEDIPHARMA LIMITED; SU, Wei-Guo; DAI, Guangxiu; XIAO, Kun; JIA, Hong; VENABLE, Jennifer Diane; BEMBENEK, Scott Damian; WO2014/15523; (2014); A1;,
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Electric Literature of 22276-95-5 , The common heterocyclic compound, 22276-95-5, name is 5-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine, molecular formula is C6H3BrClN3, 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 5-bromo-4-cUoro-7H-pyrrolo[2 -d]pyrirnidine D3 (l.OOg) inDMF (10 mL) at 0 C was added sodium hydride (0.224 g, 5.59 mmol) and the mixture stirred for 20 minutes, Benzenesulfonyl chloride (0.66 mL, 5.16 mmol) was then added dropwise and the reaction mixture stirred in the cool bath for 1 hour. The mixture was poured onto water (140 mL) and the precipitate filtered, washed with water and dried in a vacuum oven to give D5 (1.60 g) as an off white solid, lH NMR (CDC13) delta 8.77 (1H, s), 8.23 (2H, dd), 7.85 (1H, s), 7.70 (1H, m), 7.59 (2H, ddd), MS(ES+) 372 [M(Ci2H779Br35Cl 302S)+H]+. The crude product was used without further purification into the preparation of D6..

The synthetic route of 22276-95-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CONVERGENCE PHARMACEUTICALS LIMITED; WITTY, David R.; NORTON, David; TIERNEY, Jason Paul; LORTHIOIR, Ghislaine; SIME, Mairi; PHILPOTT, Karen Louise; WO2012/80735; (2012); A1;,
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Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 87591-74-0, 2-(Chloromethyl)-6-methyl-4H-pyrido[1,2-a]pyrimidin-4-one, 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, Safety of 2-(Chloromethyl)-6-methyl-4H-pyrido[1,2-a]pyrimidin-4-one, blongs to pyrimidines compound. Safety of 2-(Chloromethyl)-6-methyl-4H-pyrido[1,2-a]pyrimidin-4-one

A solution of 1H-benzo[d]imidazole (58.9 mg, 0.499 mmol), 2-(chloromethyl)-6-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (CAS 87591-74-0, 104.9 mg, 0.503 mmol), and powdered potassium carbonate (104.9 mg, 0.759 mmol) in DMF (2.50 mL) was stirred in a sealed tube at room temperature for 64 hours. The solution was diluted with methanol to 5 mL, filtered, and purified by reverse-phase HPLC to give 8 (32.07 mg, 22%) as a white solid. 1H NMR (400 MHz, DMSO-d6) ppm 2.88 (s, 3 H) 5.43 (s, 2 H) 5.81 (s, 1 H) 6.91 (d, J=6.82 Hz, 1 H) 7.19 – 7.27 (m, 2 H) 7.33 – 7.37 (m, 1 H) 7.54 – 7.59 (m, 1 H) 7.63 – 7.70 (m, 2 H) 8.35 (s, 1 H). HRMS: [M+H]+ calc. 291.124038, found 291.12374, error -1.02 ppm.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,87591-74-0, 2-(Chloromethyl)-6-methyl-4H-pyrido[1,2-a]pyrimidin-4-one, and friends who are interested can also refer to it.

Reference:
Article; Guo, Chuangxing; Linton, Angelica; Jalaie, Mehran; Kephart, Susan; Ornelas, Martha; Pairish, Mason; Greasley, Samantha; Richardson, Paul; Maegley, Karen; Hickey, Michael; Li, John; Wu, Xin; Ji, Xiaodong; Xie, Zhi; Bioorganic and Medicinal Chemistry Letters; vol. 23; 11; (2013); p. 3358 – 3363;,
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Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 10457-14-4, 2,4-Bis((trimethylsilyl)oxy)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, 10457-14-4, blongs to pyrimidines compound. SDS of cas: 10457-14-4

The reaction mixture of the compound 3 (18.0 g, 33.8 mmol) obtained in the step 2, 2,4-bis((trimethylsilyl)oxy)pyrimidine (15.2 g, 59.2 mmol) and silver trifluoromethanesulfonate (AgOTf) (13.0 g, 50.9 mmol) in acetonitrile (MeCN)/ 1,2-dichloroethene (DCE) (163 mL/163 mL) was stirred at 100 C for 5 h, cooled down to 25 C and quenched with brine. The precipitates were filtered off and the filtrate was extracted with DCM. The organic layer was dried over MgSO4, filtered and evaporated. The residue was purified by silica gel column chromatography (DCM : EtOAc = 5 : 1) to give the compound 4 (14.5 g, 64%) as a yellow solid. 1H NMR (400 MHz, CDC13) delta 8.47 (br s, 1 H), 8.07-7.92 (m, 6 H), 7.70 (d, J= 8.4 Hz, 1 H), 7.62-7.53 (m, 3 H), 7.48-7.34 (m, 6 H), 6.33 (d, J= 5.6 Hz, 1 H), 5.88 (t, J= 5.6 Hz, 1 H), 5.61 (d, J= 8.4 Hz, 1 H), 5.07-5.04 (m, 1 H), 4.93 (dd, J= 13.2, 2.8 Hz, 1 H), 4.58 (dd, J= 12.8, 3.2 Hz, 1 H).

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; KAINOS MEDICINE, INC.; SHIN, Sunmi; KIM, Hyangmi; OH, Su-Sung; WO2015/72784; (2015); A1;,
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Pyrimidine – Wikipedia

Reference of 944129-00-4, 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 944129-00-4, name is Methyl 6-amino-2-chloropyrimidine-4-carboxylate. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of methyl 6-amino-2-chloropyrimidine-4-carboxylate (260 mg, 1.39 mmol, 1.00 equiv) and 2-bromo-1,1-dimethoxyethane (1.1 g, 6.51 mmol, 4.00 equiv) in acetonitrile (6 mL) was irradiated with microwave radiation for 1 h at 120 C. The solids were collected by filtration to give the title compound (162 mg, 55%) as an off-white solid. LC-MS (ES, m/z): 212 [M+H].

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 944129-00-4, Methyl 6-amino-2-chloropyrimidine-4-carboxylate.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BLAQUIERE, Nicole; BURCH, Jason; CASTANEDO, Georgette; FENG, Jianwen A.; HU, Baihua; LIN, Xingyu; STABEN, Steven; WU, Guosheng; YUEN, Po-wai; WO2015/25026; (2015); A1;,
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Pyrimidine – Wikipedia

Related Products of 58536-46-2 ,Some common heterocyclic compound, 58536-46-2, molecular formula is C22H15BrN2, 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.

11.9 g (34 mmol) of 4-(4-bromophenyl)-2,6-diphenylpyrimidine are dissolved in 300 ml of THF and subsequently cooled to -100 C. 22 ml (38 mmol) of a 1.6M solution of n-butyllithium in hexane are slowly added dropwise to the reaction mixture with stirring. The reaction mixture is stirred for 30 min. 200 ml (34 mmol) of a solution of 2-bromo-1,3-diphenyl-2,3-dihydro-1H-benzo-1,3,2-diazaborole in toluene are subsequently added dropwise. The reaction mixture is warmed to 0 C. over a period of 4 h, then 600 ml of ethanol are added dropwise. The precipitated solid is recrystallised from toluene and subsequently sublimed. Yield: 11 g (60% of theory, purity >99.9%).

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. 58536-46-2, 4-(4-Bromophenyl)-2,6-diphenylpyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Merck Patent GmbH; Mujica-Fernaud, Teresa; Parham, Amir Hossain; Stoessel, Philipp; Pflumm, Christof; Buesing, Arne; Eberle, Thomas; (30 pag.)US10032992; (2018); B2;,
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Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 56-09-7, 2-Amino-6-hydroxypyrimidin-4(3H)-one, 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, 56-09-7, blongs to pyrimidines compound. SDS of cas: 56-09-7

a 2-Amino-4,6-dichloro-pyrimidine-5-carbaldehyde Following the method of Bell et al. (J. Heterocyclic Chem. 1983, 20, 41), to 97.0 ml (1.06 mol) phosphorus oxychloride in a 2-necked flask cooled to 5 C. was added dropwise with stirring 32.5 ml (0.42 mol) DMF. The mixture was allowed to warm to room temperature and then 25.0 g (0.20 mol) 2-amino-4,6-dihydroxy-pyrimidine was added in small portions over 30 minutes. The reaction mixture was then heated at 100 C. for 4.5 hours before being poured cautiously onto water cooled to 10 C. and left standing at room temperature overnight. The resulting crystals were collected by filtration, and extracted with 4*450 ml hot ethyl acetate.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,56-09-7, its application will become more common.

Reference:
Patent; Borroni, Edilio Maurizio; Huber-Trottmann, Gerda; Kilpatrick, Gavin John; Norcross, Roger David; US2001/27196; (2001); A1;,
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Pyrimidine – Wikipedia

Synthetic Route of 3524-87-6, 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. 3524-87-6, name is 6-Methylpyrimidin-4(3H)-one, molecular formula is C5H6N2O, 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 70 g (0.64 mol) A-1 in acetic acid is added 127 g (0.56 mol) NIS portion wise at RT within 15 min. The reaction is stirred at RT until all starting material is consumed (30 h). The reaction mixture is diluted with water and the solid product is filtered off, washed with an aqueous sodium thiosulfate solution to remove excess iodine and dried in vacuo. Yield: 90 g (60%).

According to the analysis of related databases, 3524-87-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; WUNBERG, Tobias; KRAEMER, Oliver; van der VEEN, Lars; US2013/23533; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 330786-24-8 , The common heterocyclic compound, 330786-24-8, name is 3-(4-Phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine, 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.

Intermediate 4 A mixture of about 60.67 g (0.2 mol) of (S) -2- (hydroxymethyl) piperidine-1-carboxylic acid tert-(0.3 mol) was dissolved in 360 mL of THF while 78.698 (0.3 1 01) triphenylphosphine was added. (0.3mol) of diisopropyl azodicarboxylate and 300mL of tetrahydrofuran solution, lh drop complete system slowly warming up to 30 C insulation reaction 24h, the system temperature to 0-5 (: After the reaction was complete, the solvent was evaporated, and 450 mL of methylene chloride (DCM) was added. The mixture was stirred at room temperature for 10 min, filtered, and the filtrate was bubbled with hydrogen chloride gas. The mixture was stirred for 4 h. After the reaction was complete, The organic layer was washed with 5% sodium hydrogencarbonate solution to neutral and then saturated brine, and the organic layer was dried and filtered to dryness to obtain about 62.18 g of intermediate 5 in a yield of 80.45%.

The synthetic route of 330786-24-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiangsu Zhongbang Pharmacy Limited Company; Li, Weisi; Huang, Shuang; Wu, Xiaogang; Yang, Jian; Chen, Guoping; Liu, Liping; (14 pag.)CN105859728; (2016); A;,
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