Category: pyrimidines

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. 302964-08-5, name is 2-((6-Chloro-2-methylpyrimidin-4-yl)amino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 2-((6-Chloro-2-methylpyrimidin-4-yl)amino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide

EXAMPLE 1; Preparation of the Compound of Formula (II); In a 50 mL round bottomed flask equipped with a magnetic stirrer, condenser, Ar inlet, temperature controller (J-Kem) and heating mantle was introduced compound (1) (1.0 g, 2.53 mmoles, HPLC 95.28%), N-methylpyrrolidone (6.5 mL), piperazine (0.26 g, 3.043 mmoles, 1.2 eqs) and diisopropylethylamine (0.88 mL, 5.072 mmoles, 2 eqs). The suspension was heated at 120 C. for 45 min (HPLC showed 56.3% (II), 21.1% (2) and 0.6% of starting (1)). The mixture was cooled at r.t. and diluted slowly with water (27.8 mL) to precipitate the product. The solid was collected by filtration and rinsed with water (14 mL). The solid collected showed only 45.2% of (II) along with 31.4% (2)). A white solid also crystallized out of the filtrate. The material was collected by filtration and dried under high vacuum at 40 C. for 16 hrs to give 0.22 g (0.49 mmole, 19.6% yield) of (II) as a white solid (HPLC 86.9%). HPLC system. Column; Luna C-18, 4.6×75 mm, 3 u Mobile phase A; 100% H2O+0.05% TFA Mobile phase B; 100% CH3CN+0.05% TFA Gradient; 1% B to 95% B in 15 min, hold 95% B for 2 min Flow Rate; 1 mL/min Inj. Volume; 5 uL Detection; 255 nm Column temperature; 25 C. Retention times; (II) (7.04 min), (2) (9.70 min), (1) (10.73 min). 1H NMR (400 MHz, DMSO-d6) delta 9.85 (s, 1H), 8.20 (s, 1H), 7.39 (d, 1H, Ph, J=7.6 Hz), 7.28 (d, 1H, Ph, J=7.1 Hz), 7.24 (t, 1H, Ph, J=7.7 Hz), 6.01 (s, 1H), 3.43 (m, 4H, piperazine), 2.73 (m, 4H, piperazine), 2.39 (s, 3H, CH3), 2.23 (s, 3H, CH3) ES+ MS m/z (rel. intensity) 444 (MH+, 100)

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, 302964-08-5, 2-((6-Chloro-2-methylpyrimidin-4-yl)amino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide.

Reference:
Patent; Arora, Vinod Kumar; Christopher, Lisa Joy; Cui, Donghui; Li, Wenying; US2006/211705; (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. 153435-63-3, name is 2-(Tributylstannyl)pyrimidine, molecular formula is C16H30N2Sn, 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. Formula: C16H30N2Sn

A mixture containing 4tau(4-bromo-phenyl)-piperidine-1-carboxylic acid tert-butyl ester (100 mg, 0.29 mmol), 2-tributylstannanyl-pyrimidine (130 mg, 0.36 mmol), cesium fluoride (85 mg, 0.56 mmol) and palladium di-tert-butylphosphine was degassed three times with Ar. Dioxane was added and the formed reaction mixture was stirred at 90 0C overnight under Ar. Then the reaction mixture was filter through celite and the solvent was removed under vacuum and crude product was used directly in the next step.

With the rapid development of chemical substances, we look forward to future research findings about 153435-63-3.

Reference:
Patent; SCHERING CORPORATION; WO2007/97937; (2007); 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. 1337532-51-0, name is 5-Bromo-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine. A new synthetic method of this compound is introduced below., Recommanded Product: 1337532-51-0

To a stirred solution of mixture of 1-(4-bromo-3-fluorophenyl)-3-(m-tolyl)pyrrolidin-2-one (0.5 g, 1.4 mmol, 1.0 equiv), was added bis(pinacolato)diboron (0.365 g, 1.4 mmol, 1.0 equiv), and potassium acetate (0.422 g, 4.3 mmol, 1.0 equiv), and the mixture was degassed with Argon for 10 minutes then PdCl2(dppf)-CH2Cl2 adduct (0.05 g, 0.072 mmol, 0.05 equiv) was added and again degassed with Argon for 10 minutes. The reaction mixture was stirred for 3 hours at 100 C in a sealed vessel. The reaction was cooled to room temperature. 5-bromo-7-methyl-7/-/-pyrrolo[2,3-c]pyrimidin-4-amine (0.326 g, 1.436 mmol, 1.0 equiv) and saturated aqueous NaHC03 (6 mL) was added, and Argon gas was bubbled through the reaction mixture for 10 minutes and PdCl2(dppf)-CH2Cl2 adduct (0.05 g, 0.072 mmol, 0.05 equiv) was added. The vessel was sealed, and the reaction mixture was stirred overnight at 100 C. The crude mixture was filtered through celite and the filtrate was extracted with EtOAc and dried over Na2S04 and concentrated. Purification: Purified by flash column chromatography using silica gel column, using 3 to 4 % MeOH in DCM as eluent to get desired product as white color solid. Yield: (0.055 g, 9.23%); LCMS (ES) m/z = 416.2 [M+H]+. H NMR (400 MHz, DMSOd6) delta 2.16 – 2.23 (m, 1 H), 2.30 (s, 3 H), 2.57 – 2.65 (m, 1 H), 3.74 (s, 3 H), 3.91 – 4.01 (m, 3 H), 5.98 (br s, 2 H), 7.10 (t, J=6.8 Hz, 3 H), 7.23 (t, J=6.80 Hz, 1 H), 7.30 (s, 1 H), 7.42 (t, J=8.4 Hz, 1 H), 7.59 (d, J=7.60 Hz, 1 H), 7.83 (d, J=12.8 Hz, 1 H), 8.14 (s, 1 H).

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, 1337532-51-0, 5-Bromo-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; AXTEN, Jeffrey M.; MEDINA, Jesus Raul; WO2015/136463; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 5751-20-2, 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. 5751-20-2, name is 2-(Methylthio)pyrimidin-4(3H)-one. A new synthetic method of this compound is introduced below.

To a solution containing 2.0 g (14 mmol) of 2- (methylthio) pyrimidin-4(3H)-one in 10 ml of acetic acid under a nitrogen atmosphere was added 1.04 ml (14 mmol) of bromine in 2 ml acetic acid. The reaction was allowed to stir at room temperature for 30 min. The precipitated product was filtered, washed with acetic acid and suspended in hot acetic acid- To this suspention was added 0.2 ml bromine in 1ml acetic acid. The product was collected, washed with acetic acid and recrystallized from ethanol to yield 1.4 g (45 percent) of product. 1H NMR (CD30D) 5: 2. 61 (s, 3H) , 8.29 (s, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,5751-20-2, 2-(Methylthio)pyrimidin-4(3H)-one, and friends who are interested can also refer to it.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2005/99688; (2005); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 330794-31-5, 1-Cyclopentyl-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine, 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, 330794-31-5, blongs to pyrimidines compound. Quality Control of 1-Cyclopentyl-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Synthesis of 1-(3-(4-amino-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl)phenyl)ethanone (BA81, BA81d & BA81dd); A solution of tert-butyl 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamate (200 mg, 0.76 mmol) in EtOH (3.3 ml) was added to a solution of 1-cyclopentyl-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine (BA80, 100 mg, 0.30 mmol) in DME (12 ml). Pd(PPh3)4 (30 mg, 0.03 mmol) and saturated Na2CO3 (1.9 ml) were added and the reaction was heated to 80 C. under an argon atmosphere overnight. After cooling, the reaction was extracted with saturated NaCl and CH2Cl2. Organic phases were combined, concentrated in vacuo and purified using silica gel column chromatography [MeOH-CH2Cl2, 5:95] yielding BA81. BA81 was dissolved in 50:50 CH2Cl2:TFA and stirred for one hour at room temperature. The reaction mixture was concentrated in vacuo and purified using by RP-HPLC (MeCN:H2O:0.1% TFA) to yield BA81d. BA81d was dissolved in CH2Cl2 (2 ml) and BBr3 (4 mL, 4 mol) was added slowly with a syringe, while stirring. The reaction was stirred at room temperature for 2 hours then concentrated in vacuo and purified using by RP-HPLC (MeCN:H2O:0.1% TFA) to yield BA81dd.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,330794-31-5, its application will become more common.

Reference:
Patent; Regents of the University of California; US2007/293516; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 705-24-8, 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. 705-24-8, name is 4,6-Dichloro-2-(trifluoromethyl)pyrimidine. A new synthetic method of this compound is introduced below.

To a solution of Intermediate IP (120 mg, 0.54 mmol) in DMF (3.0 mL) were added N,N-diisopropylethylamine (103 mu, 0.590 mmol) and 4, 6-dichloro-2- (trifluoromethyl)-pyrimidine (86 mu, 0.57 mmol). The solution was heated in a microwave at 90C for one hour, and was then partitioned between DCM and H20. The aqueous layer was extracted with DCM (2x), and the combined organic layers were washed with brine, dried Na2S04), filtered and concentrated in vacuo. The residue was purified by silica gel chromatography to afford Intermediate 12 (191 mg, 86%). LCMS (Method A): m/z 410.2 (M+H)+. XH NMR (CDC13): delta 7.66-7.52 (m, 3H), 7.27-7.25 (m, 2H), 6.35 (s, 1H), 4.94-4.86 (m, 1H), 4.12-4.07 (m, 1H), 4.01-3.95 (m, 1H), 3.61-3.52 (m, 2H), 2.99-2.83 (m, 3H), 2.64-2.55 (m, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,705-24-8, its application will become more common.

Reference:
Patent; VENENUM BIODESIGN LLC; HUANG, Chia-Yu; MCGUINNESS, Brian F; XU, Xiaoqing; KULTGEN, Steven G.; MCMASTER, Ellen Sieber; BEASLEY, James R.; (356 pag.)WO2018/5794; (2018); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 90213-66-4, 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.90213-66-4, name is 2,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidine, molecular formula is C6H3Cl2N3, molecular weight is 188.01, as common compound, the synthetic route is as follows.

After 2,4-dicWoro-7H-pyrrolo[2,3-d]pyrimidine (3.0 g, 16.0 mmol) was dissolved in acetone (20.0 mL), 4- methylbenzenesulfonyl chloride (4.6 g, 23.9 mmol) was added thereto. After cooling to 0 C, 2 M sodium hydroxide solution (12.0 mL) was slowly added dropwise and then stirred at room temperature for 2 hours. The organic layer was isolated, treated with magnesium sulfate, filtered, and then concentrated under reduced pressure. The residue was isolated by column chromatography to obtain a title compound (2.9 g, yield: 80.0%). [H NMR (500MHz,CD3OD) delta 8.12(d, 2H), 7.76(d, 1H), 7.37(d, 2H), 6.68(d, 1H), 2.43(s, 3H)

The chemical industry reduces the impact on the environment during synthesis 90213-66-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; DAEWOONG PHARMACEUTICAL CO., LTD.; KIM, In Woo; HAN, Mi Ryeong; YOO, Jakyung; OH, Yun Ju; KIM, Ji Duck; KIM, Nam Youn; JUN, Sun Ah; LEE, Jun Hee; PARK, Joon Seok; (197 pag.)WO2018/4306; (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. 58347-49-2, name is 7-Chloropyrazolo[1,5-a]pyrimidine. A new synthetic method of this compound is introduced below., Formula: C6H4ClN3

EXAMPLE 584-{7-Fluoro-8-methyl-3-r(l»S^-l-(pyrazolori,5-alpha1pyrimidin-7-ylamino’)ethyl]quinolin-2- yl I piperazine- 1 -carboxamide Intermediate 36 (50 mg, 0.151 mmol), 7-chloropyrazolo[l,5-alpha]pyrimidine (34.7 mg, 0.226 mmol), DIPEA (0.079 mL, 0.453 mmol) and n-BuOH (1 mL) were combined and heated under microwave irradiation at 1400C for 1 h. After cooling, the mixture was dissolved in EtOAc (100 mL) and washed with saturated brine (3 x 20 mL). The organic layer was separated, dried (MgSO4), filtered and concentrated in vacuo. Purification by preparative HPLC gave the title compound (7 mg, 10%) as a yellow solid. deltaH (DMSO-d6) 8.24 (d, J4.99 Hz, IH), 8.14 (s, IH), 8.10 (d, J2.33 Hz, IH), 7.70 (dd, J8.89, 6.22 Hz, IH), 7.25 (t, J9.13 Hz, IH), 6.58 (d, J7.55 Hz, IH), 6.51 (d, J2.33 Hz, IH), 6.40 (d, J 5.03 Hz, IH), 5.46 (s, 2H), 5.05 (t, J6.89 Hz, IH), 3.95-4.02 (m, 2H), 3.81-3.88 (m, 2H), 3.67-3.75 (m, 2H), 3.27-3.32 (m, 2H), 2.49 (d, J2.33 Hz, 3H), 1.29 (d, J6.59 Hz, 3H). LCMS (ES+) 449 (M+H)+, RT 2.59 minutes (Method 2).

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, 58347-49-2, 7-Chloropyrazolo[1,5-a]pyrimidine.

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

Electric Literature of 110099-94-0, 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 110099-94-0, name is 2-(Methylthio)pyrimidine-5-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of crude 19 (100 mg, 0.48 mmol ) in THF (5 mL) is added isobutyl chloroformate (0.05 mL, 0,58 mmol) followed by NMM (0.06 mL, 0.58 mmol) at – 10 C. After stirring for 10 minutes, the mixture is filtered and sodium borohydride (37 mg, 0,96 mmol) in water (0.2 mL) is added dropwise at 0 C. After stirring at room temperature for 20 minutes, the mixture is concentrated and the residue is partitioned between EA (20 mL) and water (10 mL). The organic layer is washed with brine (10 mL), dried over anhydrous sodium sulfate, concentrated, and purified by silica gel column chromatography (MeOH:DCM = 1 : 100) to give A38 as a colorless oil (50 mg, 74% yield). (MS: i 1 · 1 11 194.1 ).Following the procedure for A38 using 133 (1.18 g, 6.9 mmoi), NMM (695 mg.6.9 mmoi), THF (20 mL), isohutyl chioroformate (1.13 g. 8.25 mmol), sodium borodeuteride(289 mg, 6.9 mmoi), and deueterate water (0.5 mL), then purii with silica gel columnchromatography (EA:PE == 1:5) to give i13d2 as a light yellow solid (290 rng, 25%). (MS:[M+H] 159.1)

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 110099-94-0, 2-(Methylthio)pyrimidine-5-carboxylic acid.

Reference:
Patent; IMMUNE SENSOR, LLC; THE BOARD OF REGENTS OF THE UNIVERSITY OF TEXAS SYSTEM; ZHONG, Boyu; SUN, Lijun; SHI, Heping; LI, Jing; CHEN, Chuo; CHEN, Zhijian; (270 pag.)WO2017/176812; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 2217-08-5, name is 5,5-Dipropylbarbituric acid, the common compound, a new synthetic route is introduced below. Recommanded Product: 5,5-Dipropylbarbituric acid

EXAMPLE 7 1-(3-n-butoxy-2-hydroxypropyl)-5,5-dipropyl-(1H,3H,5H)pyrimidine-2,4,6-trione A solution of 5,5 dipropyl-(1H,3H,5H)-pyrimidine-2,4,6-trione (30.8 g, 0.15 mole) in dimethylformamide (30 ml) containing triethylamine (2.02 g, 0.2 mole) was mixed with butyl glycidyl ether (13 g, 0.1 mole). The mixture was heated at 60 C. for 6 hours. The solution was then diluted with water (150 ml) and extracted with toluene (2*50 ml). The organic layer was separated, washed with water (2*100 ml) dried and extracted with 5% aqueous sodium carbonate (6*100 ml). The toluene phase was then extracted with 1M aqueous sodium hydroxide (2*100 ml), the aqueous layers separated, washed with toluene (100 ml) and the pH was adjusted to 3 with sulphuric acid. The precipitated oily product was extracted with toluene (100 ml), and the organic layer was separated, washed with water, dried and evaporated to yield the title compound (16.3 g; 51.6%); purity by HPLC 96.5%.

The synthetic route of 2217-08-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sapos S.A.; US5262402; (1993); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia