Month: March 2022

Synthetic Route of 38275-61-5 ,Some common heterocyclic compound, 38275-61-5, molecular formula is C5H3ClN2O2, 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-Chloro-pyrimidine-2-carboxylic acid {4-[2-((S)-2-amino-4,5-dihydro-oxazol-4-yl)-ethyl]-phenyl}-amide The title compound was obtained in analogy to example S3 using 5-chloropyrimidine-2-carboxylic acid (CAS 38275-61-5) instead of 4-chlorobenzoic acid in step c). White solid. MS (ISP): 348.3 ([{37Cl}M+H]+), 346.1 ([{35Cl}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. 38275-61-5, 5-Chloropyrimidine-2-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hoener, Marius; Raab, Susanne; Risterucci, Celine; Sewing, Sabine; US2012/28964; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 274-71-5, 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. 274-71-5, name is Pyrazolo[2,3-a]pyrimidine, molecular formula is C6H5N3, 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 pyrazolo[1,5-ajpyrimidine (1 g, 8.39 mmol) in acetonitrile (5 mL) was added NBS (1.494 g, 8.39 mmol) and the reaction mixture stirred at room temperature for 8 h. The reaction mixture was concentrated under reduced pressure and the residue purified by silica gel chromatography (0-30% petroleum ether/EtOAc) to afford 3-bromopyrazolo[1,5-ajpyrimidine (1.2 g, 6.06 mmol, 72% yield) as a brown solid. LCMS (ESI) m/e 198.0 [(M+H), calcd for C6H5BrN3198.01; LC/MS retention time (method A2): tR = 1.43 mm.

According to the analysis of related databases, 274-71-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BRONSON, Joanne J.; CHEN, Ling; DITTA, Jonathan L.; DZIERBA, Carolyn Diane; JALAGAM, Prasada Rao; LUO, Guanglin; MACOR, John E.; MAISHAL, Tarun Kumar; NARA, Susheel Jethanand; RAJAMANI, Ramkumar; SISTLA, Ramesh Kumar; THANGAVEL, Soodamani; (318 pag.)WO2017/59080; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 1209459-80-2, 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. 1209459-80-2, name is Methyl 6-bromopyrimidine-4-carboxylate. A new synthetic method of this compound is introduced below.

Tripotassium phosphate (2eq) was added in one portion to a stirred solution of 8-chloro-6-(4,4,5,5-tetramethyl- [l,3,2]dioxaborolan-2-yl)-chroman (leq) and methyl 4-bromopyridine-2-carboxylate (2eq) in DMF (lOvol). The mixture was degassed with nitrogen for 5 minutes, after which time Pd(dppf)2C12 (0.2eq) was added in one portion, the mixture was then heated to 60oC and stirred at this temperature for 16 hours under a nitrogen atmosphere. After this time the reaction mixture was cooled to room temperature and partitioned between ethyl acetate (5 vol) and water (5 vol). The organic layer was separated, washed sequentially with water (5vol) then brine (5vol) before being dried (MgS04), filtered andconcentrated. The resulting residue was purified using a Biotage Isolera (lOOg silica column eluting with a gradient from 0% heptane to 80% DCM / 20% heptane) to give the desired compound as a white solid

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1209459-80-2, Methyl 6-bromopyrimidine-4-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; COURTNEY, Stephen Martin; PRIME, Michael; MITCHELL, William; BROWN, Christopher John; DE AGUIAR PENA, Paula C.; JOHNSON, Peter; DOMINGUEZ, Celia; TOLEDO-SHERMAN, Leticia M.; MUNOZ, Ignacio; WO2013/33085; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 1122-44-7 , The common heterocyclic compound, 1122-44-7, name is 4-Amino-5-iodopyrimidin-2(1H)-one, molecular formula is C4H4IN3O, 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 stirred solution of 4-amino-5-iodouracil (200 mg, 0.84 mmol) in anhydrous dimethylformamide (15 mL) at room temperature in a nitrogen atmosphere were added tetrakis (triphenyl phosphine)palladium (98 mg, 0.08 mmol), copper(I)iodide (32 mg, 0.17 mmol), diisopropylethylamine (0.28 mL, 1.7 mmol) and 1-phenylacetylene (0.33 mL, 2.53 mmol). The reaction mixture was stirred at room temperature. After 22 h, 10 drops of 5% of the disodium salt of EDTA/H2O were added to the reaction mixture, and the mixture was concentrated in vacuo. The residue obtained was purified on silica gel column using MeOH/CHCl3 (4:96, v/v) as an eluent to give 7. This was obtained as a solid in 67% yield; mp > 250 C; 1H NMR (DMSO-d6): delta 6.93 (s, 1H, NH2), 7.40 (m, 3H, C6H5), 7.60 (m, 2H, C6H5), 7.66 (s, 1H, NH2), 7.83 (s, 1H, H-6), 11.01 (br s, 1H, NH); 13C NMR (DMSO-d6): delta: 56.48 (C-beta), 82.30 (C-alpha), 94.18 (C-5), 128.75, 128.90, 131.61 (C-phenyl), 147.30 (C-6), 155.52 (C-2), 165.30 (C-4). FTIR (KBr) cm-1: 3461 (Ar C-H), 3399 (NH), 3139 (NH2), 2219 (C?C), 1890, 1657 (C=O), 1457, 1230, 1027, 911, 749, 687, 559 cm-1. Anal. C12H9N3O (M.W. 211.12). Calcd C 68.24, H 4.29, N 19.8. Found C 68.64, H 4.57, N 19.51.

The synthetic route of 1122-44-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Garg, Gaurav; Pande, Milind; Agrawal, Ambika; Li, Jie; Kumar, Rakesh; Bioorganic and Medicinal Chemistry; vol. 24; 8; (2016); p. 1771 – 1777;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 1159981-95-9, 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 1159981-95-9, name is 5-Bromopyrazolo[1,5-a]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 5-bromopyrazolo[1,5-a]pyrimidine (200 mg, 1.00 mmol), Pd(PPh3)4 (117 mg, 0.101 mmol), copper(I) iodide (96 mg, 0.101 mmol), and hexa-n-butylditin (0.51 mL, 1.0 mmol) in toluene (0.5 mL) at 110 C. was added ethyl (S)-2-(2-bromo-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-(tert-butoxy)acetate (0.50 g, 1.0 mmol) in toluene (3 mL) over 30 minutes. Reaction mixture was stirred nine hours at 110 C., cooled to room temperature. Ethyl acetate and lithium chloride were added and stirred over the weekend. Reaction mixture was filtered, concentrated and purified by CombiFlash (ethyl acetate/hexanes) to give desired product. LCMS-ESI+: calc’d for C28H28ClN4O3S: 535.2 (M+H+); Found 535.2 (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 1159981-95-9, 5-Bromopyrazolo[1,5-a]pyrimidine.

Reference:
Patent; Gilead Sciences, Inc.; Cai, Zhenhong R.; Guo, Hongyan; Ji, Mingzhe; Jin, Haolun; Lee, Amy; McFadden, Ryan; Mitchell, Michael L.; Munoz, Manuel; Pyun, Hyung-Jung; Xu, Lianhong; Yang, Hong; (272 pag.)US2018/118734; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 138538-42-8, name is 6-Methylpyrimidine-4-carboxylic acid. A new synthetic method of this compound is introduced below., Safety of 6-Methylpyrimidine-4-carboxylic acid

Preparative Example 8; Step A; To a 500 ml round bottom flask was added 400 mL H2O and KMnO4 (140 mmoles) and then commercially available 4,6-dimethyl-pyrmidine (35 mmole) and mixture refluxed for 20 hours. The mixture was filtered through celite and then acidified to pH 3. The aqueous was then evaporated under reduced pressure to give a solid. To the solid was then added 300 ml of methanol saturated with dry HCl. The mixture was then refluxed for 15 hours. The volatile components of the reaction mixture was then removed under reduced pressure to give an oil. To the oil was then added 150 ml of methylene chloride and organic washed with saturated NaHCO3. The aqueous was removed and then the organic layer was dried over MgSO4, filtered and then the volatile components removed under reduced pressure to give and oil. The oil was purified by column chromatography (SiO2, 10% either-methylene chloride) to give 6-methyl-pyrimidine-4-carboxylic acid.

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, 138538-42-8, 6-Methylpyrimidine-4-carboxylic acid.

Reference:
Patent; Alantos Pharmaceuticals Holding, Inc.; US2008/21024; (2008); 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 32998-03-1, name is 2,6-Dichloro-N-methylpyrimidin-4-amine. This compound has unique chemical properties. The synthetic route is as follows. name: 2,6-Dichloro-N-methylpyrimidin-4-amine

EXAMPLE 42 N-Methyl-2,6-di-(4′-t-butoxycarbonyl-1′-piperazinyl)-4-pyrimidinamine (V) A mixture of 2,6-dichloro-4-methylaminopyrimidine (III, EXAMPLE 1, 5 g) dissolved in o-xylene (300 ml) is treated with mono-t-BOC-piperazine (IV, 20.92 g) and the reaction mixture is refluxed for 50 hr. The reaction mixture is concentrated under reduced pressure. The resulting residue is partitioned between chloroform and saturated sodium bicarbonate. The organic layer is separated, washed with saline, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The crude product (24.53 g) is chromatographed on silica gel (590 g). The column is packed and eluted with chloroform/acetone (97/3). An initial fraction of 400 ml is collected followed by 8 ml fractions. Based on their TLC homogeneity, fractions 132-326 are combined and concentrated to give the title compound, NMR (CDCl3, TMS) 4.94, 4.96, 3.75-3.65, 3.55-3.4, 2.85 and 1.48 8; MS (m/z) M+ (found) 477, other ions at m/z 420, 376, 364, 348, 321,265, 221, 178, 164 and 57.

With the rapid development of chemical substances, we look forward to future research findings about 32998-03-1.

Reference:
Patent; The Upjohn Company; US5502187; (1996); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 87789-35-3, 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 87789-35-3, name is 5,7-Dichloro-2-(methylthio)thiazolo[4,5-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

Synthesis of ethyl 5-chloro-2-(methylthio)thiazolo[4,5-d]pyrimidine-7-carboxylate: The title compound was prepared from 5,7-dichloro-2-(methylthio)thiazolo[4,5-d]pyrimidine (commercially obtained from Combi-Block, San Diego, CA) using chemistry similar to that described in Example 1. ESI MS: m/z [M+H+] for C9H8ClN3O2S2, calcd 290.0, found 290.1.

According to the analysis of related databases, 87789-35-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Corvus Pharmaceuticals, Inc.; LI, Zhihong; FILONOVA, Lubov, Konstantinovna; VERNER, Erik; (375 pag.)EP3616753; (2020); 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. 830346-47-9, name is 1-(2-Fluoro-6-(trifluoromethyl)benzyl)-6-methylpyrimidine-2,4(1H,3H)-dione, molecular formula is C13H10F4N2O2, 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. Quality Control of 1-(2-Fluoro-6-(trifluoromethyl)benzyl)-6-methylpyrimidine-2,4(1H,3H)-dione

Step 1D: Preparation of 5-bromo-1-[2-fluoro-6-(trifluoromethyl)benzyl]-6- methylpyrimidine-2,4 (1H,3H)-dione 1-1; Bromine (16.5 mL, 0.32 mmol) was added to 1-[2-fluoro-6- (trifluoromethyl)benzyl]-6-methylpyrimidine-2,4(IH,3H)-dione 1c (48.5 g, 0.16 mol) in 145 mL of acetic acid. The resulting mixture became clear then formed precipitate within an hour. After 2 hours stirring, the yellow solid was filtered and washed with cold EtOAc to an almost white solid. The filtrate was washed with sat. NaHC03 and dried over Na2S04. Evaporation gave a yellow solid which was washed with EtOAC to give a light yellow solid. The two solids were combined to give 59.4 g of 1-1 (0.156 mol) total. 1H NMR (CDC13) No. 2.4 (3H, s), 5.48 (2H, s), 7.25 – 7.58 (3H, m), 8.61 (1H, s) ; MS (CI) m/z 380.9 (MH+).

With the rapid development of chemical substances, we look forward to future research findings about 830346-47-9.

Reference:
Patent; NEUROCRINE BIOSCIENCES, INC.; WO2005/113516; (2005); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 1074-68-6 ,Some common heterocyclic compound, 1074-68-6, molecular formula is C6H6N2OS, 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.

Preparation of 3-hydroxy-3-(2-methylsulfanyl-pyrimidin-4-yl)-propionic acid tert-butyl ester (18): To a cold (0 C.) solution of diisopropylamine (5.7 mL, 40.5 mmol) in THF (130 mL) is added dropwise n-butyllithium (16.2 mL of a 2.5 M solution in hexanes, 40.5 mmol). The mixture is stirred for 45 min at 0 C., then the solution is cooled to -78 C. tert-Butyl acetate (5.5 mL, 40.5 mmol) is added dropwise to the reaction mixture. After stirring 40 min at -78 C., a solution of 2-methylsulfanyl-pyrimidine-4-carbaldehyde (5.0 g, 32.4 mmol) is added dropwise. After 30 min at -78 C., the solution is poured into aqueous saturated NH4Cl. The aqueous phase is extracted with EtOAc. The organic phase is dried (MgSO4), filtered and concentrated in vacuo. The crude residue is purified over silica (5% EtOAc/hexanes, followed by 20% EtOAc/hexanes) to afford 7.2 g (82% yield) of the desired product. 1H NMR (300 MHz, CDCl3) delta 8.52 (d, J=5.1 Hz, 1H), 7.22 (d, J=5.1 Hz, 1H), 5.00 (dd, J=8.4, 3.6 Hz, 1H), 2.93 (dd, J=16.5, 3.6 Hz, 1H), 2.70 (dd, J=16.5, 7.8 Hz, 1H), 2.58 (s, 3H), 1.46 (s, 9H); ESI+ MS: m/z (rel intensity) 271.1 (85, 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. 1074-68-6, 2-Methylsulfanylpyrimidine-4-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; The Procter & Gamble Company; US2005/113392; (2005); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia