Day: February 8, 2021

Adding a certain compound to certain chemical reactions, such as: 24415-66-5, 7-Chloro-5-methyl-[1,2,4]triazolo[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, Application In Synthesis of 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine, blongs to pyrimidines compound. Application In Synthesis of 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine

Example 191[0651]2-(Fluoromethyl) -N- { (1R) -1- [3-fluoro-4- (trifluoromethyl) phenyl] -2,2-dimethylpropyl} -5-methyl [1, 2, 4] triazolo [1, 5-a] pyrimidin-7-amine[0652][0653](R) -1- [3-Fluoro-4- (trifluoromethyl) phenyl] -2, 2-dimethylpropan-1-amine hydrochloride (28.5 mg, 0.100 mmol) was added to a mixture of 7-chloro-2- (fluoromethyl) -5-methyl- [1, 2, 4] triazolo [1, 5-a] pyrimidine (20.0 mg, 0.100 mmol) in NMP (1.5 mL) . This was followed by the addition of DIEA (64.4 mg, 88 uL, 0.499 mmol) . The reaction mixture was stirred at 80 for 16 h. The resulting mixture was cooled to room temperature, diluted with water (10 mL) and extracted with ethyl acetate (3 x 15 mL) . The combined organic layers were washed with water (3 x 10 mL) , brine (3 x 10 mL) , dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by Prep-HPLC with the following conditions: Instrument, GILSON (GX-281) Column: Xbridge RP18, 5 um, 19 x 150 mm mobile phase: water (0.05NH4HCO3) and acetonitrile (40acetonitrile up to 55in 10 min, hold 100for 2 min, down to 40in 2 min) Detector, UV 220 and 254 nm. The title compound was obtainedas a solid. MS (+ESI) m/z 414.3.1HNMR(300 MHz, CD3OD) delta: 7.69-7.64 (m, 1H) , 7.52-7.44 (m, 2H) , 6.22 (s, 1H) , 5.64 (s, 1H) , 5.49 (s, 1H) , 4.76 (s, 1H) , 2.42 (s, 3H) , 1.08 (s, 9H) .

At the same time, in my other blogs, there are other synthetic methods of this type of compound,24415-66-5, 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MORRIELLO, Gregori J.; CHANG, Lehua; FOSTER, Ashley; CHEN, Yili; DWYER, Michael; GUO, Zack Zhiqiang; WANG, Ming; XU, Shimin; BO, Yingjian; FU, Jianmin; (250 pag.)WO2017/277; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 211244-81-4, 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 211244-81-4, name is 2-(Methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one (1.00 g, 5.18 mmol) in anhydrous dimethylformamide (25 mL) was added N-bromosuccinimide (0.99 g, 5.59 mmol) portionwise at room temperature, and the reaction mixture was stirred for 18 h. The mixture was concentrated, and the solid was triturated with hot water (1 x 20 mL), filtered, and washed with isopropanol to give title compound as a pale yellow solid (0.68 g, 2.50 mmol, 48%). ESMS m/z 272 (M+H)+; 1H NuMR (400 MHz, DMSO-J6) delta ppm 12.88 (br. S., 1 H), 8.84 (s, 1 H), 8.47 (s, 1 H), 2.57 (s, 3H).

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 211244-81-4, 2-(Methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one.

Reference:
Patent; AFRAXIS, INC.; CAMPBELL, David; DURON, Sergio G.; VOLLRATH, Benedikt; WADE, Warren; WO2010/71846; (2010); A2;,
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. 2915-16-4, name is 2-Chloro-4,6-diphenylpyrimidine. A new synthetic method of this compound is introduced below., Computed Properties of C16H11ClN2

Under an argon gas atmosphere, the intermediate body 1-4 (1.6 g, 3.9 mmol), the intermediate body 1-1 (1.0 g, 3.9 mmol), tris(dibenzylideneacetone)dipalladium (0.071 g, 0.078 mmol), tri-t-butylphosphonium tetrafluoroborate (0.091 g, 0.31 mmol), sodium t-butoxide (0.53g, 5.5 mmol), and anhydrous toluene (20 mL) were sequentially mixed, and heated to reflux for 8 hours. After the reaction solution was cooled down to the room temperature, an organic layer was removed and an organic solvent was distilled away under reduced pressure. The obtained residue was refined by silica-gel column chromatography, whereby a compound 1 (2.4 g, a yield of 95%) was obtained. FD-MS analysis consequently showed that m/e was equal to 638 while a calculated molecular weight was 638.

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, 2915-16-4, 2-Chloro-4,6-diphenylpyrimidine.

Reference:
Patent; Idemitsu Kosan Co., Ltd.; EP2415769; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 330786-24-8, 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. 330786-24-8, name is 3-(4-Phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine. A new synthetic method of this compound is introduced below.

Step 1 To a solution of 3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (300 mg, 1.0 mmole), triphenylphosphine (1.04 g, 3.96 mmole) and tert-butyl (2-hydroxyethyl)carbamate (238 mg, 1.5 mmoles) in THF (25 mL) was added DIAD (0.4 mL, 2 mmoles). The reaction was stirred for 5 hrs at room temperature and then water (30 mL) was added and extracted with ethyl acetate. The organic layers were combined, washed with aq. NaHCO3 and brine, then dried (Na2SO4), filtered and concentrated. The resulting tert-butyl (2-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)carbamate was used without further purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,330786-24-8, 3-(4-Phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine, and friends who are interested can also refer to it.

Reference:
Patent; Principia Biopharma Inc.; Goldstein, David Michael; US8673925; (2014); B1;,
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. 58347-49-2, name is 7-Chloropyrazolo[1,5-a]pyrimidine, molecular formula is C6H4ClN3, 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. Recommanded Product: 58347-49-2

EXAMPLE 46(S)-A- { 5,7-Difluoro-3 -[ 1 -(pyrazolof 1 ,5 -alpha]pyrimidin-7-ylamino)ethyllquinolin-2-yl} – piperazin-2-oneA solution of Intermediate 30 (61.2 mg, 0.20 mmol), 7-chloropyrazolo[l,5-alpha]- pyrimidine (33.8 mg, 0.2 mmol) and DIPEA (28.5 mg, 0.22 mmol) in M-BuOH (3 mL) was heated at 12O0C for 16 h. The solvent was removed in vacuo and the residue purified by preparative HPLC to afford the title compound (14.9 mg, 18%) as a cream solid. 6H (CDCl3) 8.45 (IH, s), 8.13 (IH, d, J5.2 Hz), 8.02 (IH, s), 7.35 (IH, dd, J 8.8 Hz), 6.90 (IH, t, J8.8 Hz), 6.88 (IH, d, J6.4 Hz), 6.55 (IH, br s), 6.48 (IH, s), 5.89 (IH, d, J5.2 Hz), 5.12-5.18 (IH, m), 4.09 (2H, q, J 17.5 Hz), 3.52-3.68 (4H, m), 1.88 (3H, d, J6.8 Hz). LCMS (ES+) 424 (M+H)+, RT 3.07 minutes {Method 1).

With the rapid development of chemical substances, we look forward to future research findings about 58347-49-2.

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

Related Products of 100644-65-3, 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. 100644-65-3, name is 4-Chloro-1H-pyrazolo[3,4-d]pyrimidin-6-amine, molecular formula is C5H4ClN5, 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.

Sodium hydride (60% dispersion in mineral oil) (354 mg, 8.85 mmol) was added portionwise to a yellow suspension of 4-chloro- 1 H-pyrazolo [3 ,4-d]pyrimidin-6- amine (A-2) (1.25 g, 7.34 mmol) in dry DMF (5 mL). l-Bromo-2-chloroethane (3.68 mL, 44.2 mmol) was added dropwise. The resulting mixture was stirred for 2 h at room temperature. The DMF was evaporated. The residue was purified by chromatography on silica gel (eluant: 0-10% methanol/ CH2C12 gradient). The product was washed with hexanes and filtered to give 4-chloro-l-(2-chloroethyl)-lH-pyrazolo[3,4-d]pyrimidin-6- amine (A-3) (409 mg, 24% yield). NMR (500 MHz, CDC13) delta ppm 3.96 (t, 2H, J=6.5 Hz), 4.59 (t, 2H, J=6.5 Hz), 5.34 (s, 2H), 7.93 (s, 1H). MS (M+l): 232, 233, 234 (2 CI).

According to the analysis of related databases, 100644-65-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; TING, Pauline, C.; MA, Shuguang; BLUMENKRANTZ, Neil; CHOWDBURY, Swapan; NEUSTADT, Bernard, R.; WO2012/135084; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 62802-42-0, 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 62802-42-0 as follows.

Step 1 : 1,1-Dimethylethyl [1-(2-fluoro-5-pyrimidinyl)-4-piperidinyl]carbamate (194)To a stirred solution of 1 ,1-dimethylethyl 4-piperidinylcarbamate (500 mg, 2.50 mmol) and diisopropylethylamine (0.871 mL, 5.0 mmol) in acetonitrile (25 mL) was added 2- chloro-5-fluoropyrimidine (0.34 mL, 2.75 mmol) via syringe at RT. The reaction mixture was heated to reflux for 19 hours, then cooled to RT and concentrated under reduced pressure. The crude oil was purified by SiO2 flash chromatography (20% to 50% EtOAc in hexanes) to give 495 mg (67%) of the title product 194 as a viscous oil. 1H NMR (400 MHz, CDCI3): delta 8.17 (s, 2 H), 4.56 – 4.52 (m, 2 H), 4.47 – 4.41 (m, 1 H), 3.70 (br s, 1 H), 3.07 – 3.00 (m, 2 H), 2.02 – 1.98 (m, 2 H), 1.44 (s, 9 H), 1.39 -1.28 (m, 2 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,62802-42-0, its application will become more common.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2008/8895; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 63810-78-6, 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. 63810-78-6, name is 5-Bromo-4-chloro-2-(methylthio)pyrimidine. A new synthetic method of this compound is introduced below.

Compound 44. A mixture of compound 42 (1.0 g, 4.22 mmol, 1.5 eq.), compound 43 (1.2 g, 2.82 mmol, 1 eq.), Pd(PPh3)4 (325 mg, 282 mumol, 0.1 eq.), and LiCl (239 mg, 5.63 mmol, 2 eq.) in toluene (10 mL) was degassed and purged with N2 for 3 times. Then the mixture was stirred at 100 C for 8 h under N2. The reaction mixture was cooled down to 25 oC and partitioned between sat. KF (30 mL) and EtOAc (40 mL). The organic phase was separated, washed with brine (20 mL), dried over Na2SO4, and concentrated in vacuo. The residue was purified by column chromatography (PE/EtOAc: 10/1 to 3/1) to afford compound 44 (400 mg, 1.18 mmol, 42% yield). 1H NMR (CDCl3, 400 MHz) delta 8.72 (s, 1H), 4.11 (s, 3H), 3.00 (d, J = 6.7 Hz, 2H), 2.57 (s, 3H), 1.07-0.92 (m, 1H), 0.57-0.46 (m, 2H), 0.32-0.17 (m, 2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,63810-78-6, 5-Bromo-4-chloro-2-(methylthio)pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; YISSUM RESEARCH DEVELOPMENT COMPANY OF THE HEBREW UNIVERSITY OF JERUSALEM LTD.; SNIR-ALKALAY, Irit; VACCA, Joseph; BEN-NERIAH, Yinon; (238 pag.)WO2019/155468; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 84905-80-6, 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.84905-80-6, name is 4-Chloro-5H-pyrrolo[3,2-d]pyrimidine, molecular formula is C6H4ClN3, molecular weight is 153.57, as common compound, the synthetic route is as follows.

Step 3: Preparation of 7-bromo-4-chloro-5H-pyrrolo[3,2-d]pyrimidine Tetrahydrofuran (5 mL) and N-bromosuccinimide (116 mg) were added to 4-chloro-5H-pyrrolo[3,2-d]pyrimidine (100 mg). The mixture was stirred for 1 hr and, upon completion of the reaction, ethyl acetate was added thereto, and washed with water. The mixture was dried over anhydrous sodium sulfate, filtered and distilled under reduced pressure to obtain the title compound. 1H NMR (300 MHz, DMSO-d6): delta 12.95 (s, 1 H), 8.71 (s, 1 H), 8.24 (d, 1 H)

Statistics shows that 84905-80-6 is playing an increasingly important role. we look forward to future research findings about 4-Chloro-5H-pyrrolo[3,2-d]pyrimidine.

Reference:
Patent; Hanmi Pharmaceutical Co., Ltd.; PARK, Chul Hyun; KIM, Won Jeoung; JUNG, Young Hee; KIM, Nam Du; CHANG, Young Kil; KIM, Maeng Sup; EP2738174; (2014); A2;,
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.7504-94-1, name is 2-Hydrazinylpyrimidine, molecular formula is C4H6N4, molecular weight is 110.1172, as common compound, the synthetic route is as follows.HPLC of Formula: C4H6N4

After adding 40 mg of 2-dimethylaminoethanol, 120 mg of triphenylphosphine and 0.200 ml of DEAD (2.2 M, toluene solution) to a 1 ml THF solution containing 100 mg of {2-(3-hydroxy-5-methoxyphenyl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene}carbamic acid methyl ester (Example (4c)) at 0 C., the mixture was stirred at room temperature for 16 hours and 30 minutes. The reaction mixture was concentrated, and the residue was crudely purified by silica gel column chromatography (ethyl acetate-heptane) to give 55 mg of a crude product. To a 1 ml DMF solution containing 55 mg of the obtained crude product there were added 12 mg of 2-hydrazinopyrimidine and 0.015 ml of triethylamine, and the mixture was stirred at 85 C. for 11 hours and 30 minutes under a nitrogen atmosphere. The reaction mixture was concentrated, and the residue was dissolved in 0.8 ml of methanol, 0.8 ml of THF and 0.1 ml of acetic acid. Next, 100 mg of sodium cyanotrihydroborate was added to the solution and the mixture was stirred at room temperature for 3 hours and 30 minutes. The reaction mixture was crudely purified by reverse-phase high performance liquid chromatography (acetonitrile-water, 0.1% acetic acid) to give a crude product. To a solution of the obtained crude product in 2.4 ml of a methanol:water:acetic acid=1:1:1 mixed solvent there was added 100 mg of iron powder, and the mixture was stirred at 65 C. for 18 hours and 30 minutes under a nitrogen atmosphere. After filtering the reaction mixture, it was crudely purified by reverse-phase high performance liquid chromatography (acetonitrile-water, 0.1% acetic acid) to give a crude product. The obtained crude product was optically resolved using a SUMICHIRAL OA-2500 column, and the first eluting enantiomer (4.35 mg) of the title compound was obtained as a light yellow solid. 1H-NMR (CD3OD) delta 1.92 (s, 6H) 2.49 (s, 6H) 2.96 (dd, J=5.2, 5.6 Hz, 2H) 3.76 (s, 3H) 4.14 (dd, J=5.2, 5.6 Hz, 2H) 5.58 (s, 1H) 6.47 (t, J=2.0 Hz, 1H) 6.77 (t, J=2.0 Hz, 2H) 6.85 (d, J=8.8 Hz, 2H) 7.30 (t, J=4.8 Hz, 1H) 7.60 (d, J=8.8 Hz, 2H) 8.77 (d, J=4.8 Hz, 2H) HPLC retention time: 11 min

At the same time, in my other blogs, there are other synthetic methods of this type of compound,7504-94-1, 2-Hydrazinylpyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Eisai R&D Management Co., Ltd.; US2008/15199; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia