Pyrimidines

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. 374930-88-8, name is tert-Butyl 4-(5-bromopyrimidin-2-yl)piperazine-1-carboxylate, molecular formula is C13H19BrN4O2, 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. SDS of cas: 374930-88-8

To a solution of dicyclohexylamine (3.43 g, 18.94 mmol) in THF (60 mL) at -78 C. was added n-BuLi (2.5 M, 7.9 mL, 18.94 mmol) dropwise. The mixture was stirred at RT for 10 min, followed by the addition of methyl 2-(4-fluorophenyl)acetate (2.69 g, 16.02 mmol) in toluene (60 mL). After stirred at RT for another 10 min, tert-butyl 4-(5-bromopyrimidin-2-yl)piperazine-1-carboxylate (5.0 g, 14.57 mmol), Pd2(dba)3 (667 mg, 0.728 mmol) and P(t-Bu)3 (10%, 1.47 g, 0.728 mmol) were added sequentially. The reaction mixture was stirred at RT for 15 h, quenched by water (150 mL) and extracted with EA. The combined organic layers were washed with water and brine, dried over Na2SO4, filtered and concentrated. The residue was passed a column (silica gel, PE_EA=6:1) to afford the title compound (0.5 g, 8%) as an orange solid. MS (ES+) C22H27FN4O4 requires: 430. found: 431 [M+H]+.

With the rapid development of chemical substances, we look forward to future research findings about 374930-88-8.

Reference:
Patent; Hodous, Brian L.; Kim, Joseph L.; Wilson, Kevin J.; Wilson, Douglas; Zhang, Yulian; US2015/111887; (2015); A1;,
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Reference of 4595-60-2, 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 4595-60-2 as follows.

A mixture of 4-chloro-3-nitrophenylboronic acid (520 mg, 2.58 mmoles), 2-bromopyrimidine (410 mg, 2.58 mmoles), tetrakis(triphenylphosphine)palladium(0) (100 mg, 0.08 mmoles) and sodium carbonate (800 mg, 7.5 mmoles) in water (2.5 ml_) and dimethylformamide (15 ml_) was heated at 1000C for 1hour. Water was added and the mixture extracted with ethyl acetate (x2). The combined extracts were dried and evaporated then chromatographed (dichloromethane-methanol) to give the title compound (390 mg, 64%). 1 H NMR (400 MHz, CHLOROFORM-d) delta ppm 7.32 (t, J=4.93 Hz, 1 H) 7.69 (d, J=8.59 Hz, 1 H) 8.64 (dd, J=8.34, 2.02 Hz,1 H) 8.87 (d, J=5.05 Hz, 2 H) 9.02 (d, J=2.02 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,4595-60-2, its application will become more common.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2006/127458; (2006); A2;,
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Pyrimidine – Wikipedia

Electric Literature of 330786-24-8, Adding some certain compound to certain chemical reactions, such as: 330786-24-8, name is 3-(4-Phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine,molecular formula is C17H13N5O, 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 330786-24-8.

9g tri-n-butylphosphine dissolved in 100mL anhydrous tetrahydrofuran and cooled down to 0-5 degrees.9g of diisopropyl azodicarboxylate was added dropwise under N2 protection. After the addition was completed,The reaction temperature was controlled at 0-5 degrees for 1 h. The above tributylphosphine andA mixture of diisopropyl azodicarboxylate was slowly poured into 4 g of solution3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine andIn 3.5 g of (S)-1-Boc-3-hydroxypiperidine in 50 mL of anhydrous tetrahydrofuran,Stir 0-5 degrees overnight. After the reaction liquid is concentrated under reduced pressure,Purification by column to obtain the product 6.8g, yield 75%

According to the analysis of related databases, 330786-24-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shanghai Fupu Biological Technology Co., Ltd.; Liu Zheng; (13 pag.)CN106279284; (2017); A;,
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Application of 5177-27-5, 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.5177-27-5, name is 5-Amino-2,4-dichloropyrimidine, molecular formula is C4H3Cl2N3, molecular weight is 163.9927, as common compound, the synthetic route is as follows.

A mixture of Pd(OAc)2 (20 mg, 0.070 mmol), PPh3 (80 mg, 0.30 mmol), potassium (2-furyl)trifluoroborate (530 mg, 3.00 mmol), K2CO3 (340 mg, 2.46 mmol), and 2,4-dichloropyrimidine-5-amine (8d) (200 mg, 1.20 mmol) in EtOH (50 mL, 96%) was stirred at 80 C for 16 h under Ar, and evaporated in vacuo. The product was purified by flash chromatography on silica gel eluting with EtOAc/CH2Cl2/hexane (1:5:5); yield 220 mg (80%), mp 173-175 C (dec), yellow solid. 1H NMR (CDCl3, 300 MHz) delta 8.28 (s, 1H, H-4), 7.62 (dd, J=1.7, 0.8 Hz, 1H, H-5 in furyl), 7.53 (dd, J=1.7, 0.8 Hz, 1H, H-5 in furyl), 7.37 (dd, J=3.5, 0.8 Hz, 1H, H-3 in furyl), 7.12 (dd, J=3.5, 0.8 Hz, 1H, H-3 in furyl), 6.61 (dd, J=3.5, 1.7 Hz, 1H, H-4 in furyl), 6.50 (dd, J=3.5, 1.7 Hz, 1H, H-4 in furyl), 3.86 (br s, 2H, NH2); 13C NMR (CDCl3, 75 MHz) delta 153.3 (C-2 in furyl), 152.5 (C-2 in furyl), 148.7 (C-2, C-5, or C-6), 145.8 (C-4), 144.0 (C-5 in furyl), 143.8 (C-5 in furyl), 139.1 (C-2, C-5, or C-6), 134.1 (C-2, C-5, or C-6), 112.8 (C-3 in furyl), 112.4 (C-4 in furyl), 112.0 (C-4 in furyl), 110.4 (C-3 in furyl); MS EI m/z (rel %) 227 (100, M+), 198 (37), 171 (7), 114 (6), 78 (6); HRMS (EI) calcd for C12H9N3O2: 227.0695. Found 227.0694.

The chemical industry reduces the impact on the environment during synthesis 5177-27-5, I believe this compound will play a more active role in future production and life.

Reference:
Article; Read, Matthew L.; Krapp, Andreas; Miranda, Pedro O.; Gundersen, Lise-Lotte; Tetrahedron; vol. 68; 7; (2012); p. 1869 – 1885;,
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Application of 3177-24-0, 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 3177-24-0 as follows.

[00607] General conditions for the preparation of 2-amino-4-chloropyrimidine-5-carbonitrile:[00608] To a solution of 2,4-dichloropyrimidine-5-carbonitrile (E-1) (2.0 g, 11.5 mmol) in 1,4-dioxane (20 mL) at 0 C, ammonium hydroxide (28-30%, 4.4 mL, 34.5 mmol) is added dropwise, and the resulting mixture is stirred while warming from 0 C to RT for 2 h. Then, the mixture is partitioned between ethyl acetate (200 mL) and water (50 mL). The organic layer is washed with brine, dried over Na2SO4 and filtered. The filtrate is mixed with silica gel and then concentrated in vacuo. The residue is purified by silica gel chromatography eluting with 0- 100% ethyl acetate/hexanes to afford the product (E-2) (917 mg) and a mixture of (E-2) and (E-3). Additional (E-3) can be obtained from this mixture by a second column chromatographic purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3177-24-0, its application will become more common.

Reference:
Patent; INFINITY PHARMACEUTICALS, INC.; CASTRO, Alfredo, C.; EVANS, Catherine, A.; WO2015/168079; (2015); A1;,
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Synthetic Route of 934524-10-4, 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 934524-10-4, name is 2,4-Dichloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

A solution of 2,4-dichloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine (0.35g, 1.0 mmol), D-alaninol (0.10 mL, 1.3 mmol) and TEA (0.20 mL, 1.4 mmol) in dioxane (6 mL) was stirred at 7O0C for 20 h. Water and EtOAc were added. The organic phase was washed with IN HCl, then with 5% NaHCO3, dried over Na2SO4, concentrated in vacuo to give (R)-2-(2-chloro-7- tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)propan-l-ol (0.38 g).

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 934524-10-4, 2,4-Dichloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine.

Reference:
Patent; PORTOLA PHARMACEUTICALS, INC.; WO2009/131687; (2009); A2;,
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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. 287714-35-6, name is Methyl 2-chloropyrimidine-5-carboxylate. This compound has unique chemical properties. The synthetic route is as follows. name: Methyl 2-chloropyrimidine-5-carboxylate

Example A6; a).Preparatipn.of intermediate 32; A solution of 2-chloro-5-pyrimidinecarboxylic acid, methyl ester (0.058 mol) in /V5TV- dimethyl- acetamide (80ml) was added dropwise to a solution of 4- piperidinemethanamine (0.116 mol) and TV-ethyl -TV-(I -methyl ethyl)- 2-propanamine (0.145 mol) in TV^N-dimethyl- acetamide (150ml) under N2 flow. The mixture was stirred at room temperature for 1 hour and 30 minutes, poured out into ice water and extracted with EtOAc, then with DCM. The organic layer was washed with water, dried (MgSO4), filtered and the solvent was evaporated. The residue was crystallized from DIPE. The precipitate was filtered off and dried, yielding 1Og (65%) of intermediate 32.

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, 287714-35-6, Methyl 2-chloropyrimidine-5-carboxylate.

Reference:
Patent; JANSSEN PHARMACEUTICA N.V.; WO2006/136553; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 38275-57-9, 5-Bromopyrimidine-2-carbonitrile, 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, category: pyrimidines, blongs to pyrimidines compound. category: pyrimidines

D. 1-(5-bromopyrimidin-2-yl)ethanone To a 50 mL 1 neck flask equipped with magnetic stirrer, nitrogen inlet and thermometer was charged 0.68 grams (g) of 5-Bromo-pyrimidine-2-carbonitrile (3.7 mmol), and 20 mL of anhydrous ether. The solution was cooled to ~0 C., and the methyl magnesium bromide solution 3.0M in ether; 1.1 ml, 3.3 mmol) was added dropwise. Allowed to slowly warm to room temperature, and quenched with aqueous ammonium chloride solution. Extracted with 3*50 mls of ether and washed with brine. Dried over anhydrous magnesium sulfate, and concentrated under vacuum on a rotary evaporator. The crude product thus obtained was chromatographed on silica gel with ethyl acetate and hexane. afforded 0.22 g of a white solid which was consistent with the title compound upon analysis by NMR. The NMR data is as follows: 300 MHz 1H NMR (CDCl3, TMS=0 ppm) 2.75 (s, 3H); 9.00 (s 2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,38275-57-9, 5-Bromopyrimidine-2-carbonitrile, and friends who are interested can also refer to it.

Reference:
Patent; DOW AGROSCIENCES LLC; US2009/253708; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 3177-20-6, 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 3177-20-6, name is Methyl 2,4-dichloropyrimidine-5-carboxylate. This compound has unique chemical properties. The synthetic route is as follows.

Following the preparation protocol of Section5.1.2.1, the reaction mixture of methyl 2,4-dichloropyrimidine-5-carboxylate (8e) (228 mg, 1.10 mmol), K2CO3 (276 mg,2.0 mmol) and 4-hydroxyl benzo[d]oxazole (3) (135 mg, 1.0 mmol)in DMF (1 mL) and acetone (9 mL) was stirred at 40 C for 6 h togive compound 9g as a white solid (268 mg, 87.7percent); mp 131?133C; 1H NMR (400 MHz, DMSO d6) d (ppm) 9.13 (s, 1H), 8.76 (s, 1H),7.80 (d, J = 8.0 Hz, 1H), 7.56 (t, J = 8.0 Hz, 1H), 7.37 (d, J = 8.0 Hz,1H), 3.93 (s, 3H); HRMS (ESI): m/z, Calcd. for C13H9O4N3Cl[M+H]+: 306.0276, Found 306.0273

According to the analysis of related databases, 3177-20-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Cui, Guonan; Jin, Jing; Chen, Hualong; Cao, Ran; Chen, Xiaoguang; Xu, Bailing; Bioorganic and Medicinal Chemistry; vol. 26; 8; (2018); p. 2186 – 2197;,
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Electric Literature of 282102-07-2, 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 282102-07-2, name is 2-Chloro-4-methoxy-5-nitropyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

d.2 [2-(4-Methoxy-5-nitro-pyrimidin-2-yloxy)-ethyl]-propyl-carbamic acid te/t-butyl esterTo a solution of (2-hydroxy-ethyl)-propyl-carbamic acid te/t-butyl ester(1.07 g, 5.28 mmol) in THF (40 ml) at 0C was added NaH (0.25 g, 5.80 mmol). After stirring the suspension at 00C for 30 minutes a solution of 2-chloro-4-methoxy-5-nitropyrimidine (1 g, 5.28 mmol) in THF (10 ml) was added and the mixture was stirred at room temperature for 16 h. The mixture was added to water, which was extracted three times with dichloromethane.The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure to obtain the title compound.MS (ESI) m/z: 357.15 [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 282102-07-2, 2-Chloro-4-methoxy-5-nitropyrimidine.

Reference:
Patent; ABBOTT GMBH & CO. KG; WO2007/118859; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia