Pyrimidines

Electric Literature of 51674-77-2 ,Some common heterocyclic compound, 51674-77-2, molecular formula is C7H4ClN3, 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 5-{3-[(1S)-1-aminoethyl]-5-chloro-2-methoxy-6-methylphenyl}-N,N-dimethylpyridine-2-carboxamide dihydrochloride (17 mg, 0.040 mmol), 4-chloropyrido[3,2-d]pyrimidine (6.7 mg, 0.040 mmol) and N,N-diisopropylethylamine (35 muL, 0.20 mmol) in 1-butanol (0.4 mL) was heated at 120 C. for 2 h. The mixture was purified on prep-LCMS (Sunfire Prep C18 5 mum 30¡Á10 mm column, flow rate 60 mL/min, eluting with a gradient of acetonitrile and water with 0.05% TFA) to afford the title product (2.7 mg, 14%). LCMS calculated for C25H26ClN6O2 (M+H)+: m/z=477.2. found: 477.2.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,51674-77-2, its application will become more common.

Reference:
Patent; INCYTE CORPORATION; Li, Yun-Long; Combs, Andrew P.; US2015/361094; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 67831-83-8 ,Some common heterocyclic compound, 67831-83-8, molecular formula is C7H7N3OS, 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 (35m) (1.0 g, 5.5 mmol) in POCI3 (10 mL) cooled at 5C on an ice bath was added dropwise diethylaniline (1.0 mL, 6.2 mmol). After 2 hours stirring at 80C, the mixture was poured on crushed ice and the resulting precipitate was filtered off and purified by silica gel column chromatography.Yield: 33%.Melting point: 206-208C.H NMR (DMSO -d6) d 2.56 (s, 3H, S CH3), 6.52 (s, 1H, 5 -H), 7.52 (s, 1H, 6 -H), 12.39 (s, 1H, N H). 13C NM R (DMSO -d6) d 13.8 (SCH3), 99.0 (C-5), 113.2 (C-4a), 126.9 (C-6), 150.4-152.7 (C-4/C-7a),162.7 (C-2).

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. 67831-83-8, 2-(Methylthio)-7H-pyrrolo[2,3-d]pyrimidin-4-ol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; UNIVERSITE DE LIEGE; LANCELLOTTI, Patrizio; OURY, Cecile; PIROTTE, Bernard; (140 pag.)WO2019/158655; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 51940-64-8, 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.51940-64-8, name is Ethyl 2,4-Dichloro-5-pyrimidinecarboxylate, molecular formula is C7H6Cl2N2O2, molecular weight is 221.0407, as common compound, the synthetic route is as follows.

Potassium carbonate (62.50 g, 452.41 mmol) was added to ethyl 2,4-dichloropyrimidine-5-carboxylate (40.00 g, 180.97 mmol) and tetrahydro-2H-pyran-4-amine hydrochloride (24.90 g,10 181.0 mmol) in acetonitrile (1 L). The reaction mixture was stirred at rt for 16 h. The resultingprecipitate was collected by filtration, washed with THF (750 mL) and the combined organic layerswere concentrated in vacuo. The crude product was purified by fcc, elution gradient 0 to 2% THFin DCM, to afford the title compound (37.74 g, 73%) as a pale yellow solid; 1H NMR (400 MHz,DMSO) 1.32 (3H, t), 1.54-1.63 (2H, m), 1.85-1.89 (2H, m), 3.43-3.49 (2H, m), 3.83-3.88 (2H, m),15 4.12-4.26 (lH, m), 4.29-4.34 (2H, m), 8.34 (lH, d), 8.64 (lH, s); m/z MH+ 286.

The chemical industry reduces the impact on the environment during synthesis 51940-64-8, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ASTRAZENECA AB; CANCER RESEARCH TECHNOLOGY LIMITED; FINLAY, Maurice, Raymond, Verschoyle; GOLDBERG, Frederick, Woolf; HOWARD, Martin, Richard; TING, Attilla, Kuan, Tsuei; (145 pag.)WO2019/238929; (2019); 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.33097-13-1, name is 4,6-Dichloro-2-(methylthio)pyrimidine-5-carbonitrile, molecular formula is C6H3Cl2N3S, molecular weight is 220.08, as common compound, the synthetic route is as follows.Safety of 4,6-Dichloro-2-(methylthio)pyrimidine-5-carbonitrile

Example 43 Synthesis of 5-(4-(2-cyano-3-cyclopropylacrylamido)benzylamino)-7-(3,5-dimethoxyphenylamino)-imidazo[1,2-c]pyrimidine-8-carboxamide Step 1. To a solution of 4,6-dichloro-2-(methylthio)pyrimidine-5-carbonitrile (14 g, 63.6 mmol, 1.0 eq) and 3,5-dimethoxyaniline (9.94 g, 63.6 mmol, 1.0 eq) in THF (300 mL) at 0 C., was added DIEA (12.32 g, 95.4 mmol, 1.5 eq). The resulted mixture was stirred at RT for 4 h. The reaction mixture was diluted with water (30 mL), filtered and dried to give 4-chloro-6-(3,5-dimethoxy-phenylamino)-2-methylsulfanyl-pyrimidine-5-carbonitrile (19 g, 89% in yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,33097-13-1, 4,6-Dichloro-2-(methylthio)pyrimidine-5-carbonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Taunton, JR., John William; Brameld, Kenneth Albert; Goldstein, David Michael; Mcfarland, Jesse; Krishnan, Shyam; Choy, Jonathan; US2014/323464; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 58347-49-2, 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 58347-49-2 as follows.

EXAMPLE 242-rDimethylaminoVl-(4-{7-fluoro-8-methyl-3-r(lS)-l-rpyrazolori.5-alpha1pyrimidin-7- ylamino)ethyl1quinolin-2-vUpiperazin- 1 -vDethanone Intermediate 15 (700 mg, 2.06 mmol), 2-(dimethylamino)-l-(piperazin-l-yl)- ethanone (500 mg), ?-BuOH (10 mL) and DIPEA (2 mL) were combined in a sealed tube and heated to 13O0C for 13 days. The reaction mixture was cooled, concentrated onto silica and purified by column chromatography (SiO2, 0-10% MeOH in EtOAc) to give a white solid. This material, MeOH (8 mL) and 2N HCl in Et2O (4 mL) were combined and stirred at r.t. for 2 days. The reaction mixture was concentrated to give a yellow foam. A portion of this material (50 mg, 0.12 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 to 13O0C for 16 h. The reaction mixture was then concentrated to dryness and purified by preparative HPLC to give the title compound (28 mg, 48%) as a tan glass. deltaH (DMSO-Ci6) 8.64 (IH, s), 8.41 (IH, d, J7.80 Hz), 8.13 (2H, m), 7.74 (IH, dd, J8.95, 6.28 Hz), 7.33 (IH, t, J9.13 Hz), 6.44 (IH, d, J2.27 Hz), 6.28 (IH, d, J5.30 Hz), 5.21- 5.13 (IH, m), 4.16-3.73 (4H, m), 3.42-3.17 (6H, m), 2.56 (3H, s), 2.25 (6H, s), 1.89 (3H, d, J 6.71 Hz). LCMS (ES+) 491 (M+H)+, RT 3.23 minutes {Method 1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,58347-49-2, its application will become more common.

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 57473-32-2, 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 57473-32-2, name is 5,7-Dichloroimidazo[1,2-a]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Example 8. General Procedure H A mixture of the desired chloroimidazopyrimidines i-H (1 equiv), desired aminomethyl heterocycle or benzylamine ii-H (1.2 equiv), and triethylamine (NEt3) (1.5-3.5 equiv) in 1,4-dioxane (~0.1 M) was stirred at 70 C until the reaction was complete by LC-MS and/or TLC analysis. The crude reaction mixture was directly purified by silica gel chromatography (typical eluents included, for example, a mixture of hexanes and EtOAc, or a mixture of CH2Cl2 and MeOH, or an 80:18:2 mixture of CH2Cl2/CH3OH/concentrated NH4OH) to afford the desired product iii-H. The product structures prepared according to General Procedure H were confirmed by 1H NMR and/or by mass analysis.

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 57473-32-2, 5,7-Dichloroimidazo[1,2-a]pyrimidine.

Reference:
Patent; THE GENERAL HOSPITAL CORPORATION; UNITED STATES DEPARTMENT OF HEALTH AND HUMAN SERVICES; SLAUGENHAUPT, Susan, A.; JOHNSON, Graham; PAQUETTE, William, D.; ZHANG, Wei; MARUGAN, Juan; (306 pag.)WO2016/115434; (2016); 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. 767-15-7, name is 2-Amino-4,6-dimethylpyrimidine, molecular formula is C6H9N3, 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: 2-Amino-4,6-dimethylpyrimidine

General procedure: For the synthesis of 2, the solution of sulfurisocyanatidic chloride (7.2mmol) in 20mL toluene was added to the solution of 1 (6.0mmol) in 20mL toluene dropwise at room temperature. The reactant was heated to 140C and then the reaction proceeded for 18h under reflux. Subsequently, the mixture was cooled down to room temperature and remaining sulfurisocyanatidic chloride was removed under reduced pressure, together with the solvent. Without further purification, the resulting yellow oil 2 was dissolved in 10mL anhydrous acetonitrile and after that it was added slowly to 5mmol of 3, which was also dissolved in 10mL anhydrous acetonitrile beforehead in ice bath. After stirring for 24hat room temperature, acetonitrile was removed under reduced pressure and saturated sodium bicarbonate was added to product 4. Product 5 precipitated easily and it was further purified by recrystallization from petroleum ether/acetone in 1:1 ratio in high yields. 15% hydrochloric acid was added to aqueous solution of 5 under stirring and corresponding acidified product 4 precipitated out easily in high yields.

With the rapid development of chemical substances, we look forward to future research findings about 767-15-7.

Reference:
Article; Wu, Ren-Jun; Ren, Tongtong; Gao, Jie-Yu; Wang, Li; Yu, Qilin; Yao, Zheng; Song, Guo-Qing; Ruan, Wei-Bin; Niu, Cong-Wei; Song, Fu-Hang; Zhang, Li-Xin; Li, Mingchun; Wang, Jian-Guo; European Journal of Medicinal Chemistry; vol. 162; (2019); p. 348 – 363;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 49844-90-8, 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. 49844-90-8, name is 4-Chloro-2-(methylthio)pyrimidine, molecular formula is C5H5ClN2S, 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 4-chloro-2-(methylthio)-pyrimidine (21,9.90 g, 61.6 mmol) in MeOH (28 mL) and MeCN (20 mL)mixed solution, NBS (13.16 g, 73.9 mmol) was added(2 ¡Á 6.58 g). After the additions, the reaction mixture wasstirred at room temperature. After quenching with saturatedNa2SO3solution, the solution was extracted with DCMand saturated NaHCO3solution three times. The combinedorganic phases were dried over MgSO4,filtered, and concentrated in vacuo. The residue was purified by passingthe organic extract through a silica gel column using PE/EA(25:1) to give the product 22 (Elliott 1981). White solid;yield 73%; m.p. 48.5-50.1 C; 1H NMR (300 MHz, CDCl3)delta 8.54 (s, 1H), 2.55 (s, 3H); 13C NMR (75 MHz, CDCl3)delta172.1, 159.5, 114.1, 14.7; HRMS ([M + H]+): m/z calcd for[(C5H4BrClN2S) + H]+: 240.90254, found: 240.90203.

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 49844-90-8, 4-Chloro-2-(methylthio)pyrimidine.

Reference:
Article; Li, Shu-ting; Chen, Jun-qing; Feng, Cheng-liang; Yang, Wan-feng; Ji, Min; Chemical Papers; vol. 73; 12; (2019); p. 3043 – 3051;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 42754-96-1, 4,6-Dichloro-1H-pyrazolo[3,4-d]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 4,6-Dichloro-1H-pyrazolo[3,4-d]pyrimidine, blongs to pyrimidines compound. Application In Synthesis of 4,6-Dichloro-1H-pyrazolo[3,4-d]pyrimidine

TMSOTf (1.04 g, 4.72 mmol) and DBU (532 mg, 3.54 mmol) were added to a solution of 5b (520 mg, 1.18 mmol) and 4,6-dichloro-1H-pyrazolo[3,4-djpyrimidine (220 mg, 1.18 mmol) in MeCN (14 mL) successively. After the reaction mixture was stirred at rt for 2 h, it was poured into sat.aq. NaHCO3 and extracted with EtOAc. The organic layer was washed with brine, dried and concentrated in vacuo. The residue was purified by column chromatography (Si02, 33% EtOAc petroleum ether) to afford the title compound (5c) (250 mg, 38% yield) as a mixture of two diastereomers.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,42754-96-1, 4,6-Dichloro-1H-pyrazolo[3,4-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; ORIC PHARMACEUTICALS, INC.; DU, Xiaohui; EKSTEROWICZ, John; FANTIN, Valeria R.; JACKSON, Erica L.; SUN, Daqing; YE, Qiuping; MOORE, Jared; ZAVOROTINSKAYA, Tatiana; (262 pag.)WO2019/90111; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 873-83-6 ,Some common heterocyclic compound, 873-83-6, molecular formula is C4H5N3O2, 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.

General procedure: A mixture of 2-hydroxynaphthalene-1,4-dione (0.17 g, 1 mmol), 4-chlorobezaldehyde(0.14 g, 1 mmol), 6-amino-uracil (0.12 g, 1 mmol), and p-TSA (0.05 g) in refluxing water (5 mL) was stirred for 6 h. After completion of the reaction as confirmed by thin-layer chromatography (TLC) (eluent EtOAc=n-hexane, 1:3), the reaction mixture was cooled to room temperature. The precipitated product was separated by filtration, washed three times with water and 5mL acetone, and dried at 60?70 ¡ãC. Corresponding products were analytically pure without recrystallization.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,873-83-6, its application will become more common.

Reference:
Article; Azizian, Javad; Delbari, Akram Sadat; Yadollahzadeh, Khadijeh; Synthetic Communications; vol. 44; 22; (2014); p. 3277 – 3286;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia