Day: September 22, 2021

Adding a certain compound to certain chemical reactions, such as: 58347-49-2, 7-Chloropyrazolo[1,5-a]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, Safety of 7-Chloropyrazolo[1,5-a]pyrimidine, blongs to pyrimidines compound. Safety of 7-Chloropyrazolo[1,5-a]pyrimidine

EXAMPLE 18N-r(35r)-l-{7-Fluoro-8-methyl-3-r(15r)-l-(pyrazolorL5-alphalpyrimidin-7-ylamino>;)ethyl1- quinolin-2-vUpyrrolidin-3-yl]cyclopropanecarboxamide(5)-(-)-3 -Amino- 1-pyrrolidinecarboxylic acid tert-butyl ester (500 mg, 2.68 mmol), DCM (30 mL), DIPEA (2 mL) and cyclopropanecarbonyl chloride (0.275 mL, 3 mmol) were combined at r.t. under a nitrogen atmosphere. The reaction mixture was stirred for 1 day, then diluted with DCM (50 mL) and washed with water (50 mL). The organic layer was separated, dried (MgSO4) and concentrated in vacuo to give a brown oil. This oil, MeOH (10 mL) and 2N HCl in Et2O (5 mL) were stirred at r.t. for 3 days. The reaction mixture was then concentrated in vacuo. The resulting material, Intermediate 15 (500 mg, 1.48 mmol), H-BuOH (16 mL) and DIPEA (2 mL) were combined in a sealed tube and heated to 13O0C for 15 days. The reaction mixture was cooled, concentrated onto silica and purified by column chromatography (SiO2, 0-100% EtOAc in isohexane) to give a tan solid. This material, MeOH (10 mL) and 2N HCl in Et2O (7 mL) were combined and stirred at r.t. for 24 h. The reaction mixture was concentrated to give a brown glass. A portion of this material (50 mg, 0.127 mmol), n- BuOH (6 mL), DIPEA (1 mL) and 7-chloropyrazolo[l,5-alpha]pyrimidine (50 mg, 0.25 mmol) were combined in a sealed tube and heated under microwave irradiation to 16O0C for 2 h. The reaction mixture was then concentrated to dryness and purified by preparative HPLC to give the title compound (32.3 mg, 54%) as a brown glass. 6H (DMSO-d6) 8.44 (IH, d, J6.91 Hz), 8.38 (IH, d, J6.91 Hz), 8.25 (IH, s), 8.17 (IH, d, J 2.27 Hz), 8.10 (IH, d, J5.21 Hz), 7.57 (IH, dd, J8.84, 6.41 Hz), 7.10 (IH, t, J9.10 Hz), 6.49 (IH, d, J2.27 Hz), 6.06 (IH, d, J 5.28 Hz), 5.27 (IH, m), 4.50-4.42 (IH, m), 4.07- 3.94 (2H, m), 3.82-3.74 (IH, m), 3.60 (IH, dd, J 10.47, 5.21 Hz), 2.51 (3H, s), 2.32-2.23 (IH, m), 2.04-1.94 (IH, m), 1.77 (3H, d, J6.54 Hz), 1.66-1.58 (IH, m), 0.77-0.67 (4H, m). LCMS (ES+) 474 (M+H)+, RT 2.51 minutes {Method I).

The synthetic route of 58347-49-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UCB PHARMA S.A.; ALLEN, Daniel, Rees; BROWN, Julien, Alistair; BUeRLI, Roland; HAUGHAN, Alan, Findlay; LANGHAM, Barry, John; MATTEUCCI, Mizio; OWENS, Andrew, Pate; RAPHY, Gilles; SHARPE, Andrew; WO2010/133836; (2010); A1;,
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.591-55-9, name is 5-Aminopyrimidine, molecular formula is C4H5N3, molecular weight is 95.1, as common compound, the synthetic route is as follows.Computed Properties of C4H5N3

General procedure: A solution of Pd(OAc)2 and BINAP in dry toluene was warmed at 45 C for 5 min. The leaving group-containing purine was then added under N2 bubbling; the mixture was kept at 45 C for 10 min. and KOtBu was added. After 10 min, the appropriate nucleophile was added. The mixture was heated at 100 C under N2 until reaction completion (3 h to 2 days depending upon the nucleophile used). After cooling to room temperature,the mixture was filtered through Celite, and concentrated. The residue was dissolved in CH2Cl2 (75 mL) and washed (1 × 10 mL) with water and brine (2 × 10 mL). The organic layer was dried and concentrated under vacuum. The residue was purified by chromatography on silica gel using various amounts of EtOAc/cyclohexane/ethanol as eluants.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,591-55-9, 5-Aminopyrimidine, and friends who are interested can also refer to it.

Reference:
Article; Houz, Sandrine; Hoang, Nha-Thu; Lozach, Olivier; Le Bras, Jacques; Meijer, Laurent; Galons, Herv; Demange, Luc; Molecules; vol. 19; 9; (2014); p. 15237 – 15257;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 32779-37-6 , The common heterocyclic compound, 32779-37-6, name is 2,5-Dibromopyrimidine, molecular formula is C4H2Br2N2, 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.

11126] To a solution of intermediate B-S (520 g, 2.45 mmol) in DMA (8.2 mE) was added DIPEA (0.84 mE, 4.90 mmol) followed by 2,5-dibromopyrimidine (661 g, 2.69 mmol). The reaction mixture was heated at 120 C. for 30 minutes using microwave and was then diluted with water and EtOAc. The aqueous phase was extracted twice with EtOAc and the combined organic layers were washed with a saturated solution of NaC1, dried over Mg504, filtered and evaporated. Purification via silica gel chromatography (0-40% EtOAc in hexanes) gave the title compound (651 g, 72%). MS (ESI): mass calcd. for C,5H2,BrN4O2, 368.1; m/z found, 370.9 [M+H]. ?H NMR (500 MHz, CDC13) oe 8.28 (is, 2H),5.56 (s, 1H), 4.29 (s, 1H), 4.23-4.15 (m, 1H), 3.99-3.91 (m, 1H), 2.03-1.93 (m, 1H), 1.87-1.63 (m, 2H), 1.62-1.32 (m, 12H).

The synthetic route of 32779-37-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Janssen Pharmaceutica NV; COATE, Heather R.; DVORAK, Curt A.; FITZGERALD, Anne E.; LEBOLD, Terry P.; PREVILLE, Cathy; SHIREMAN, Brock T.; (473 pag.)US2016/46640; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 3934-20-1, Adding some certain compound to certain chemical reactions, such as: 3934-20-1, name is 2,4-Dichloropyrimidine,molecular formula is C4H2Cl2N2, 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 3934-20-1.

Under nitrogen, 100mL three-mouthed flask successively add 002-2 (1.3g, 8.73mmol), 13mL DME, FeCl3 (1.414g, 8.72mmol) and 001-5 (974mg, 7.43mmol). In an oil bath at 64 deg.C react overnight. After completion of the reaction, the reaction mixture was down to room temperature, filtered, the filter cake washed 3 times with 20mL of methanol, the organic phases were combined and concentrated to dryness, and driedto give 1.0g 005-1 (47%), as a yellow solid.

According to the analysis of related databases, 3934-20-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shanghai Shaletech Technology Co., Ltd; Jiang, Yueheng; (28 pag.)CN105237515; (2016); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 51-20-7, 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. 51-20-7, name is 5-Bromouracil. A new synthetic method of this compound is introduced below.

General procedure: Nitrogenous compounds (1eq. each) viz. thymine (for 2), 5-bromouracil (for 3), adenine (for 4), were first dissolved in warm DMSO. To this solution TEA and a solution of [6]-shogaol (1eq.) in DMSO was added. Reaction mixture was stirred at room temperature for 24h. The crude product was extracted using ethyl acetate (3×50mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated under reduced pressure to get crude product as a syrupy residue which was further purified by flash chromatography to afford the corresponding pure product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,51-20-7, 5-Bromouracil, and friends who are interested can also refer to it.

Reference:
Article; Singh, Vinay Kr; Doharey, Pawan K.; Kumar, Vikash; Saxena; Siddiqi; Rathaur, Sushma; Narender, Tadigoppula; European Journal of Medicinal Chemistry; vol. 93; (2015); p. 74 – 82;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 3764-01-0, 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 3764-01-0, name is 2,4,6-Trichloropyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

The 4-chloro-2-(2-difluoromethylbenzimidazol-l-yl)-6-mophiholinopyrimidine used as a starting material was prepared as follows :-; Diisopropylethylamine (6.3 g) was added to a stirred solution of 2,4,6-trichloropyrimidine (10 g) in methylene chloride (100 ml) that had been cooled to 0°C. Morpholine (4.3 g) was added slowly and the resultant reaction mixture was stirred at ambient temperature for 3 hours. The mixture was washed with a saturated aqueous sodium bicarbonate solution. The organic layer was separated, dried over magnesium sulphate and evaporated. The residue was purified by column chromatography on silica using an increasingly polar solvent gradient from mixtures of isohexane and methylene chloride. The more polar isomeric product was collected. There was thus obtained 2,4-dichloro- 6-morpholinopyrimidine as a solid (7.8 g); NMR Spectrum: (DMSOd6) 3.60-3.74 (m, 8H), 6.96 (s, IH); Mass Spectrum: M+H+ 234.

According to the analysis of related databases, 3764-01-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; BUTTERWORTH, Sam; GRIFFEN, Edward, Jolyon; PASS, Martin; WO2008/32072; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 3934-20-1, Adding some certain compound to certain chemical reactions, such as: 3934-20-1, name is 2,4-Dichloropyrimidine,molecular formula is C4H2Cl2N2, 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 3934-20-1.

Example 2 Preparation of Intermediate 4-(4-chloro-pyrimidin-2-yl)-piperazine-1-carboxylic Acid Tert-Butyl Ester (I-2a): To a suspension of 2,4-dichloropyrimidine (1.00 g, 6.71 mmol) in 13.4 mL of toluene was added 4-methyl-piperazine-1-carboxylic acid tert-butyl ester (1.34 g, 6.71 mmol). The reaction was heated to reflux overnight, then cooled to room temperature and concentrated in vacuo. The residue was taken up in 20 mL of water and extracted with ethyl acetate (2*40 mL). The combined organic layers were washed with brine (25 mL), then dried over sodium sulfate, filtered, and concentrated in vacuo to an off-white solid. Flash column chromatography (silica gel, gradient elution from 5% ethyl acetate-hexanes to 20% ethyl acetate-hexanes) yielded 1.14 g of the title compound (I-2a). 1H NMR (400 MHz, CDCl3) delta 8.15 (d, 1H); 6.52 (d, 1H); 3.80 (m, 4H); 3.48 (m, 4H); 1.47 (s, 9H). MS (APCI+) Calc: 298, Found: 299.1 (M+1).

According to the analysis of related databases, 3934-20-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chiang, Phoebe; Novomisle, William A.; Welch JR., Willard M.; US2003/105106; (2003); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 3680-69-1 ,Some common heterocyclic compound, 3680-69-1, molecular formula is C6H4ClN3, 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 4-chloro-7H-pyrrolo[2,3-d] pyrimidine (15.4 g,0.100 mol) in tetrahydrofuran, 60% sodium hydride (8.0 g, 0.200 mol)was added in batches under ice bath. The reaction mixture was stirredunder ice bath for 0.5 h, and then chloromethyl pivalate (30.1 g,0.200 mol) was added to the mixture. Subsequently, the reaction wasstirred at room temperature for 1.5 h. After completed, the mixture waspoured into saturated ammonium chloride solution. The mixture wasextracted with ethyl acetate (50 ml×5), the organic layer was washedwith brine, dried over anhydrous Na2SO4, and then filtered and concentratedto yield 4 as a yellow solid (27.5 g, 85.0%). MS (ESI) m/z:268.4 [M+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. 3680-69-1, 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Jiang, Feng; Zang, Linghe; Miao, Xiuqi; Jia, Fang; Wang, Jie; Zhu, Minglin; Gong, Ping; Jiang, Nan; Zhai, Xin; Bioorganic and Medicinal Chemistry; vol. 27; 18; (2019); p. 4089 – 4100;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 96548-91-3, 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 96548-91-3, name is 2-Fluoropyrimidin-4-amine. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 2-fluoropyrimidin-4-amine (1.94 g, 17.1 mmol), ethyl 4-chloro-2-phenylpyrimidine-5-carboxylate (3.0 g, 11.4 mmol) and cesium carbonate (5.57 g, 17.1 mmol, Aldrich) was heated to 85 C. for 18 h. The mixture was cooled to RT, diluted with H2O and extracted with CH2Cl2 (2*) and CHCl3 (2*). The combined organics were dried over Na2SO4, Filtered and concentrated. Purifications by flash chromatography (0?15?50% EtOAc/Hexanes) afforded the title product. MS m/z 340 (MH)+.

According to the analysis of related databases, 96548-91-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Andersen, Denise Lyn; Chang, Catherine H.; Falsey, James R.; Frohn, Michael J.; Hong, Fang-Tsao; Liao, Hongyu; Liu, Longbin; Lopez, Patricia; Retz, Daniel Martin; Rishton, Gilbert M.; Rzasa, Robert M.; Siegmund, Aaron; Tadesse, Seifu; Tamayo, Nuria; Tegley, Christopher M.; US2006/69110; (2006); A1;,
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. 6972-27-6, name is 6-Chloro-1,3-dimethylpyrimidine-2,4(1H,3H)-dione, molecular formula is C6H7ClN2O2, 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. COA of Formula: C6H7ClN2O2

Step 2: 6-(hydroxyamino)-l,3-dimethylpyrimidine-2,4(lH,3H)-dione: A solution of Step 1 intermediate (10 g, 57.261 mmol), hydroxylamine hydrochloride (12.15 g, 176.361 mmol) and sodium acetate (33.81 g, 412.28 mmol) in isopropyl alcohol (280 ml) were refluxed for 4 h. The reaction mixture was concentrated under reduced pressure, diluted with water and stirred for 1 h. The precipitated solid was collected by filtration, washed with water (25 ml) and dried to obtain 9.56 g of the product as a pale brown solid; NMR (300 MHz, DMSO-i/6) delta 3.07 (s, 3H), 3.16 (s, 3H), 3.67 (s, 2H), 10.45 (br s, lH).

With the rapid development of chemical substances, we look forward to future research findings about 6972-27-6.

Reference:
Patent; GLENMARK PHARMACEUTICALS S.A.; CHAUDHARI, Sachin, Sundarlal; KUMAR, Sukeerthi; THOMAS, Abraham; PATIL, Nisha, Parag; KADAM, Ashok, Bhausaheb; WAGHMARE, Nayan, Taterao; KHAIRATKAR-JOSHI, Neelima; MUKHOPADHYAY, Indranil; WO2011/114184; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia