Day: June 4, 2021

Reference of 1224944-77-7, 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.1224944-77-7, name is Ethyl 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate, molecular formula is C9H8ClN3O2, molecular weight is 225.63, as common compound, the synthetic route is as follows.

Nitrogen was bubbled through a solution of ethyl 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate (5.40 g, 23.94 mmol) in dioxane/EtOH H2O (130 mL, 20:3:3). 2-(trifluoromethyl)phenylboronic acid (6.80 g, 35.90 mmol), Pd(PPh3)4 (2.80 g, 2.39 mmol), and Cs2CO3 (15.60 g, 47.88 mmol) were added and the reaction mixture was heated at reflux for 2 h. The mixture was cooled to room temp, poured into EtOAc (300 mL) washed with brine, dried (MgSO4), and concentrated. The crude residue was purified by MPLC eluting with pentane/EtOAc (0-100%) to give ethyl 5-(2-(trifluoromethyl)phenyl)pyrazolo[1,5-a]pyrimidine-3-carboxylate (6.30 g, 78 % yield). MS (ESI) calcd for C16H12F3N3O2 (m/z): 335.09; found: 336 [M+H]

Statistics shows that 1224944-77-7 is playing an increasingly important role. we look forward to future research findings about Ethyl 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate.

Reference:
Patent; SIRTRIS PHARMACEUTICALS, INC.; CASAUBON, Rebecca, L.; NARAYAN, Radha; OALMANN, Christopher; VU, Chi, B.; WO2013/59587; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 3680-69-1, Adding some certain compound to certain chemical reactions, such as: 3680-69-1, name is 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine,molecular formula is C6H4ClN3, 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 3680-69-1.

3H, m), 2.4 (3H, s), 1.31 (3H, J=6.8 Hz, d); MS (ES+) [M+H]+=455.6.15. Example 15(S)-N-(3-bromophenyl)-4-(5-chloro-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-N’-cyano-2-methylpiperazine-1-carboximidamide A. Preparation of 4,5-dichloro-7H-pyrrolo[2,3-d]pyrimidine: 4-Chloro-pyrrolo[2,3-d]pyrimidine (0.5 g, 3.26 mmol) was suspended in anhydrous CH2Cl2 (25 ml), and N-chlorosuccinimide (0.87 g, 6.52 mmol) was added. The reaction mixture was refluxed for 3 days, then cooled to room temperature. The white solid was collected by filtration to give 5-dichloro-7H-pyrrolo[2,3-d]pyrimidine (0.54 g, 2.9 mmol, 88%).1H NMR (CD3OD): delta 8.57 (1H, s), 7.60 (1H, s); MS (ES+) [M+H]+=188.

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:
Patent; Harrison, Bryce Alden; Kimball, Spencer David; Mabon, Ross; Rawlins, David Brent; Rice, Dennis S.; Voronkov, Michael Victor; Zhang, Yulian; US2009/42893; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 10397-13-4, 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 10397-13-4, name is 4-(4,6-Dichloropyrimidin-2-yl)morpholine. This compound has unique chemical properties. The synthetic route is as follows.

0388] To a slurry of 2-mophiholino-4,6-dichloropyrimidine (prepared as inMethod 22, 2.0 g, 8.54 mmol) in NMP (14 mL), triethylamine (1.43 mL, 10.25 mmol) was added. The heterogeneous mixture was stirred for 15 minutes, then treated with morpholine (0.75 mL, 8.54 mmol). Upon refluxing at 85 0C under argon for 2 hours, the solution was cooled, then added to EtOAc (160 mL). The organic solution was washed with 25 mL of NaHCO3(sat.) (2 x), water (2 x) and brine, dried over Na2SO4, filtered and concentrated. The crude material was dissolved in 200 mL EtOAc and filtered through a SiO2 pad, further eluting with EtOAc, yielding 2.2 g (93%) of 2,4-dimorpholino-6- chloropyrimidine as an off-white solid. LCMS (m/z): 285.0 (MH+), 1H NMR (CDCl3): delta 5.86 (s, IH), 3.71-3.76(m, 12H), 3.52-3.56(m, 4H).

According to the analysis of related databases, 10397-13-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; WO2007/84786; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 287714-35-6, 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 287714-35-6, name is Methyl 2-chloropyrimidine-5-carboxylate. This compound has unique chemical properties. The synthetic route is as follows.

To a mixture of compound 5 (200 mg, 562.09 umol, 1 eq, HCl) in DMSO (5 mL) was added Cs2CO3 (549.42 mg, 1.69 mmol, 3 eq) and 5A (97.00 mg, 562.09 umol, 1 eq) at 25 C, the reaction was stirred at 15 C for 10 hr. LCMS showed compound 5 was consumed completely and one main peak with desired mass was detected. The reaction mixture was added water (15 mL), filtered and the filtered cake was concentrated under reduced pressure to give a residue. The crude product was used into the next step without further purification. Compound 6 (210 mg, 413.53 umol, 73.57% yield, 89.69% purity) was obtained as a white solid, and checked by HNMR and HPLC. LCMS: RT = 1.421 min, MS cal.: 455.1, [M+H]+ = 456.1. 1H NMR (400MHz, CHLOROFORM-d) d ppm 8.85 (s, 2H), 6.79 – 6.74 (m, 2H), 6.72 – 6.66 (m, 2H), 4.70 (s, 2H), 4.61 (td, J = 4.9, 14.0 Hz, 2H), 3.89 (s, 3H), 3.82 – 3.76 (m, 3H), 3.73 (s, 3H), 3.69 – 3.59 (m, 2H), 2.11 (ddd, J = 4.1, 9.6, 13.6 Hz, 2H), 1.84 – 1.66 (m, 2H). HPLC: RT= 2.725 min. In some embodiments, LCMS and/or HPLC runs for compounds of the present disclosure may use different conditions and different retention times for the same compound may be observed for different runs.

According to the analysis of related databases, 287714-35-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KLEO PHARMACEUTICALS, INC.; BUNIN, Anna; IBEN, Lawrence G.; MANION, Douglas; SPIEGEL, David Adam; WELSCH, Matthew Ernest; (397 pag.)WO2019/136442; (2019); 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 63558-65-6, name is 4-Chloro-5-iodopyrimidine. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C4H2ClIN2

Step 1: (l-BenzyI-lH-pyrazol-3-yl)(4-chloropyrimidin-5-yl)methanol 4-Chloro-5-iodopyrimidine (300 mg, 1.25 mmol) was weighed into a 100 mL 2 necked RBF and the flask was purged with argon. This starting material was dissolved in THF (10 mL) and the solution was cooled to -78 C. To the solution was added n-Butyllithium (2.50 M in hexane; 1.0 mL, 2.5 mmol) at -78 C and then the mixture was stirred for 30 min. To this mixture was added dropwise a solution of 1 -benzyl- lH-pyrazole-3-carbaldehyde (211 mg, 1.1 mmol) in THF (4 mL), and the resulting mixture was stirred for 30 min. The reaction was quenched by addition of saturated NH4CI (50 mL) and extracted with EtOAc (50 mLx4). The combined organic layers were washed with brine, dried over Na2S04, filtered, and concentrated in vacuo. The residue was purified on silica gel to provide (1-benzyl- lH-pyrazol-3-yl)(4-chloropyrimidin-5-yl)methanol (304 mg, 85%) as a light yellow oil. LCMS (FA): m/z = 301.4 (M+H).

With the rapid development of chemical substances, we look forward to future research findings about 63558-65-6.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; DUFFEY, Matthew, O.; ENGLAND, Dylan, B.; HU, Zhigen; ITO, Mitsuhiro; LANGSTON, Steven, P.; MCINTYRE, Charles; MIZUTANI, Hirotake; XU, He; WO2015/2994; (2015); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 115617-41-9, 4,5-Dichloro-6-ethylpyrimidine, 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, 115617-41-9, blongs to pyrimidines compound. COA of Formula: C6H6Cl2N2

(1) Synthesis of 5-chloro-6-ethyl-4-[alpha-(2,2,3-trifluorobenzo-1,4-dioxane-6-yl) ethylamino] pyrimidine 0.7 g (4.0 mmol) of 4,5-dichloro-6-ethylpyrimidine which is a material compound (IIb), 0.8 g (3.4 mmol) of 1-(2,2,3-trifluorobenzo-1,4-dioxane-6-yl)ethylamine which is a material compound (IIIc) and a catalytic amount of 4-(N,N-dimethylamino)pyridine were suspended in 5 ml of triethylamine and the suspension was heated under reflux for 5 hours. After the reaction, extraction with toluene and washing with water were conducted. After drying with anhydrous sodium sulfate, toluene was removed by evaporation under reduced pressure. The resulting oily product was purified by silicagel column chromatography (Wako gel C-200, eluted with toluene:ethyl acetate = 5:1) to give 0.5 g of the desired compound as colorless oily product (indicated in Table 12 as Compound No. 41).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,115617-41-9, its application will become more common.

Reference:
Patent; UBE INDUSTRIES, LTD.; EP424125; (1991); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 22536-66-9 ,Some common heterocyclic compound, 22536-66-9, molecular formula is C5H4ClN3O, 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.

A mixture of DIEA (0.111 ml, 0.635 mmol), (S)-3-(1-aminoethyl)-6-chloroquinolin-2(1H)-one II-1 (70.7 mg, 0.317 mmol), and 2-chloropyrimidine-4-carboxamide (50 mg, 0.317 mmol) in DMSO (2 ml) was heated to 110 C. for overnight, added EtOAc, washed with water, dried and concentrated. The biotage purification with 0-5% MeOH/DCM on a 25 g column afforded (S)-2-((1-(6-chloro-2-oxo-1,2-dihydroquinolin-3-yl)ethyl)amino)pyrimidine-4-carboxamide I-114 (49 mg, 44.9%). 1H NMR (300 MHz, DMSO-d6): delta 11.02 (br s, 1H), 8.45 (d, J=4.7 Hz, 1H), 8.00 (br, 1H), 7.79 (br, 2H), 7.72 (s, 1H), 7.47 (d, J=8.79 Hz, 1H), 7.28 (d, J=8.8 Hz, 1H), 7.02 (d, J=4.69 Hz, 1H), 5.29 (m, 1H), 1.41 (d, J=7.04 Hz, 3H).

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. 22536-66-9, 2-Chloropyrimidine-4-carboxamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Forma Therapeutics, Inc.; Lin, Jian; Ericsson, Anna; Campbell, Ann-Marie; Gustafson, Gary; Wang, Zhongguo; Diebold, R Bruce; Ashwell, Susan; Lancia, JR., David R.; Caravella, Justin Andrew; Lu, Wei; (171 pag.)US2016/83365; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 4994-86-9, 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. 4994-86-9, name is 4-Chloro-2-methylpyrimidine, molecular formula is C5H5ClN2, 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.

A mixture of 4-chloro-2-methylpyrimidine (0.2 g, 1.556 mmol), (3-fluoro-4- methoxyphenyl)boronic acid (0.264 g, 1.556 mmol), and CS2CO3 (1.014 g, 3.11 mmol) in 1,4-dioxane (5 mL) and water (3 mL) was purged with nitrogen gas for 30 min. The reaction mixture was added PdCh (dppfJ-CfhCh adduct (0.127 g, 0.156 mmol) and was again purged with nitrogen gas for 10 min. The reaction mixture was heated at 80 C for 12 h. The reaction mixture was allowed to cool to room temperature and was concentrated under reduced pressure. The residue was taken up in ethyl acetate (50 mL) and water (40 mL), then the biphasic mixture was filtered through celite. The celite was washed with ethyl acetate (50 mL). The aqueous layer was separated out and the organic layer was dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to afford a brown solid. The crude solid was purified by silica gel chromatography (EtOAc in pet ether) to afford 4-(3- fluoro-4-methoxyphenyl)-2-methylpyrimidine (0.128 g, 0.587 mmol, 38% yield) as a light yellow solid as an off-white color solid. LCMS (ESI) m/e 219.1 [(M+H)+, calcd for C12H12FN2O 219.1]; LC/MS retention time (method B): fe. = 0.69 min.

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 4994-86-9, 4-Chloro-2-methylpyrimidine.

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; (485 pag.)WO2017/59085; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 10397-13-4, 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.10397-13-4, name is 4-(4,6-Dichloropyrimidin-2-yl)morpholine, molecular formula is C8H9Cl2N3O, molecular weight is 234.08, as common compound, the synthetic route is as follows.

(4S,5R)-4-Methyl-5-thiazol-2-yl-oxazolidin-2-one (4.70 g, 20.1 mmol) was dissolved in 70 mL of DMF and cooled to 0 C. NaH (964 mg, 60% in oil, 24.1 mmol) was added under argon, and the reaction mixture was stirred for 30 minutes at 0 C. 4-(4,6-dichloropyrimidin-2-yl)morpholine (3.70 g, 20.1 mmol) dissolved in 30 mL of DMF was added, and the reaction mixture was stirred for 3 hours at 0 C., followed by stirring at RT for 2 hours. The reaction was then quenched by addition of aqueous NH4Cl, followed by dilution with EtOAc; the organic solvents were separated, washed with brine, dried over MgSO4, filtered, and concentrated. The residue was purified by column chromatography (80 g SiO2) using EtOAc in hexane from 0% to 100% in order to give the title compound (3.64 g, 48%). LC-MS: [M+H] 382.2, 384.1; Rt 1.10 min; (LCMS method 1). 1H NMR (400 MHz, CHCl3-d): 7.77 (d, 1H), 7.38-7.33 (m, 2H), 5.39 (d, 1H), 5.07-4.98 (m, 1H), 3.75-3.55 (m, 8H), 1.64 (d, 3H).

Statistics shows that 10397-13-4 is playing an increasingly important role. we look forward to future research findings about 4-(4,6-Dichloropyrimidin-2-yl)morpholine.

Reference:
Patent; NOVARTIS AG; Fairhurst, Robin Alec; Furet, Pascal; Kalthoff, Frank Stephan; Lerchner, Andreas; Rueeger, Heinrich; US2014/135330; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 5604-46-6, 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 5604-46-6, name is 2-Amino-4,6-dichloropyrimidine-5-carbaldehyde. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of tert-butyl (3S)-3-ethylpiperazine-l -carboxylate (0.5 g, 2.3 mmol) and 2-amino-4,6-dichloropyrimidine-5-carbaldehyde (0.45 g) in 1,4-dioxane (8.0 mL) was added DIPEA (1.2 mL, 7.0 mmol). The reaction mixture was heated at 120C overnight in a sealed Wheaton vial, then cooled and stirred at room temperature over the weekend. The solvent was removed in vacuo, and the residue was partitioned between water and DCM. The organic layers were phase separated and concentrated in vacuo to give the title compound (0.85 g, 99%) as a yellow glass. LCMS (ES+) [M+H]+ 370, RT 1.81 minutes (method 2).

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 5604-46-6, 2-Amino-4,6-dichloropyrimidine-5-carbaldehyde.

Reference:
Patent; UCB PHARMA S.A.; KATHOLIEKE UNIVERSITEIT LEUVEN, K.U.LEUVEN R&D; FORD, Daniel James; FRANKLIN, Richard Jeremy; GHAWALKAR, Anant Ramrao; HORSLEY, Helen Tracey; HUANG, Qiuya; REUBERSON, James Thomas; VANDERHOYDONCK, Bart; WO2014/96423; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia