Category: pyrimidines

Reference of 13036-50-5, 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. 13036-50-5, name is 2-Chloro-4-phenylpyrimidine. A new synthetic method of this compound is introduced below.

A mixture of 2-chloro-4-phenylpyrimidine (71 mg, 0.37 mmol), Intermediate 20 (100 mg, 0.34 mmol) and DIPEA (120 muIota_, 0.68 mmol) in NMP (1 mL) was heated at 130C for 3 hrs. The reaction mixture was allowed to cool to ambient temperature and diluted with water (10 mL). The crude product was extracted into diethyl ether (20 mL), dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by chromatography on the Biotage Companion (12 g column, 0 to 100% diethyl ether in isohexane) to afford the title compound as a gum (65 mg). LCMS (Method A): Two peaks at 2.45 min and 2.66 min, 451 [M+H]+.1H NMR (400 MHz, DMSO-d6, 374 K) 8.36 (d, 0.8 H), 8.30 (bd, 0.2 H), 8.15-8.07 (m, 1 .6 H), 7.97 (bm, 0.3 H), 7.56-7.46 (m, 3.92 H), 7.46-7.24 (m, 7.38 H), 7.16-7.05 (m, 1.8 H), 6.33 (bs, 1 H), 4.41 (td, 1 H), 3.71 (m, 1 H), 3.50 (m, 1 .1 H), 3.26 (bm, 0.2 H), 2.84 (s, 0.3 H), 2.82 (s, 0.3 H), 2.63 (s, 0.3 H), 2.48 (s, 2.1 H), 1 .82 (bm, 0.7 H), 1.00 (d, 2.5 H), 0.78 (bd, 0.5 H), 0.56 (bs, 3 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,13036-50-5, 2-Chloro-4-phenylpyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; C4X DISCOVERY LIMITED; BLANEY, Emma Louise; MARTIN, Barrie Phillip; NOWAK, Thorsten; WATSON, Martin John; (212 pag.)WO2016/34882; (2016); 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.703-95-7, name is 5-Fluoro-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid, molecular formula is C5H3FN2O4, molecular weight is 174.0867, as common compound, the synthetic route is as follows.SDS of cas: 703-95-7

Dissolve 5-fluoroorotic acid (Compound 1) (40g, 0.23mol) in N,N-dimethylformamide (500mL). Slowly add DBU (35.0g, 0.23mol) dropwise, stir at room temperature for 1h, then slowly drop iodomethane (32.0g, 0.23mol), and stir at 60 C for 4h. After the reaction was completed, 100 mL of ice water was added with stirring to precipitate a solid, which was filtered, and the filter cake was washed with water (100 mL x 3) and dried in vacuo to obtain compound 2 (30 g, yield = 70%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,703-95-7, 5-Fluoro-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; Suzhou Ruiming Drug Discovery Co., Ltd.; Zhang Fei; Feng Zixia; (33 pag.)CN110950868; (2020); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 934524-10-4, 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 934524-10-4 as follows.

A stirred solution of S-2 (5.00 g, 14.6 mmol) in EtOH (50 mL) taken in a round- bottom flask was charged with DIPEA (5.0 mL, 29.2 mmol) and S-11 (1.74 g, 20.5 mmol) at room temperature. The reaction mixture was heated to 80C for 5 h under nitrogen atmosphere and was concentrated under reduced pressure. The crude residue was purified by column chromatography on silica gel using 0- 50% EtOAc in hexanes as eluent to afford S- 12 (3.80 g, 65%, AMRI lot IN-SKY-C-11) as an off-white solid. The compound was characterized by 1H NMR analysis.1H NMR (400 MHz, CDCl3): delta 8.08 (d, J = 8.36 Hz, 2H), 7.39 (d, J = 4 Hz, 1H), 7.30 (d, J = 8.12 Hz, 2H), 6.43 (d, J = 4 Hz, 1H), 5.25 (d, J = 7.48 Hz, 1H), 3.7 (q, J = 14.44 Hz, 1H), 2.39 (s, 3H), 1.28 (d, J = 6.52 Hz, 3H), 0.91- 0.87 (m, 1H), 0.56- 0.41 (m, 2H), 0.39- 0.24 (m, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,934524-10-4, its application will become more common.

Reference:
Patent; SOUTHERN RESEARCH INSTITUTE; AUGELLI-SZAFRAN, Corinne, E.; SUTO, Mark; GALEMMO, Robert; MOUKHA-CHAFIQ, Omar; GUPTA, Vandana; ANANTHAN, Subramaniam; (254 pag.)WO2017/106771; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 53554-29-3, 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. 53554-29-3, name is Ethyl 2-(methylthio)-6-oxo-1,6-dihydropyrimidine-5-carboxylate, molecular formula is C8H10N2O3S, 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.

General procedure: To a Radley reaction carousel tube, add 1 equivalent 1, 1.1 equivalents of the amine, a stir bar, and 5 mL 95% ethanol. Reflux while stirring for 24 hours. After cooling to room temperature the resulting precipitate was collected by vacuum filtration, washing with 10 mL deionized water and 5 mL chloroform.

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 53554-29-3, Ethyl 2-(methylthio)-6-oxo-1,6-dihydropyrimidine-5-carboxylate.

Reference:
Article; Watkins, Sydney M.; Ghose, Debarati; Blain, Joy M.; Grote, Dakota L.; Luan, Chi-Hao; Clare, Michael; Meganathan; Horn, James R.; Hagen, Timothy J.; Bioorganic and Medicinal Chemistry Letters; vol. 29; 20; (2019);,
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. 153286-94-3, name is 5-Ethynylpyrimidine, molecular formula is C6H4N2, 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. COA of Formula: C6H4N2

To a mixture of (iS)-2-(l-((6-am.ino-5-iodopyrimidin-4-y].)amino)ethyl)-3- cyclopropyl-5-(I -methyl- lH-pyrazol-4-yl)qumazolin-4(3H)-one (40.0 mg, 0.08 mmol) and 5- ethynylpyrimidine (12.0 mg, 0.12 mmol ) in DMF (1 .5 mL) was added Pd(PPh3)2Cl2 (1 1.0 mg, 0.02 mmol), Cul (2.0 mg, 0.01 mmol) and triethylamine (0.05 mL, 0.4 mmol), then the mixture was purged with nitrogen and heated at 90 C under N2 atmosphere for 17 hours. The mixture was cooled to rt, then concentrated in vacuo, and the residue was purified by a flash silica gel column chromatography (DCM/MeOH (v/v) =20/1) to give the title compound as an off-white solid (9.0 mg, yield 23.5%). MS (ESI, pos. ion) m/z: 505.4 [M+H]+; FontWeight=”Bold” FontSize=”10″ H NMR (600 MHz, CDCb) delta (ppm): 9.23 (s, 1 H), 8.97 (s, 2 H), 8.22 (s, 1 H), 7.67 (s, 1 H), 7.66-7.65 (t, J= 7.7 Hz, 1 H), 7.63 (s, 1 H), 7.43-7.42 (dd, J = 8.1, 1.1 Hz, 1 H), 7.35-7.33 (dd, J = 7.5, 1.2 Hz, 1 H), 6.86-6.85 (d, J = 7.8 Hz, 1 H), 6.22-6.18 (dq, J = 13.4, 6.7 Hz, 1 H), 5.37 (s, 2 H), 4.00 (s, 3 H), 3.03-2.99 (m, 1 H), 1.65-1.64 (d, J = 6.6 Hz, 3 H), 1.44-1.42 (m, 2 H), 1.06- 1.01 (m, 1 H), 0.87-0.86 (m, 1 H).

With the rapid development of chemical substances, we look forward to future research findings about 153286-94-3.

Reference:
Patent; CALITOR SCIENCES, LLC; SUNSHINE LAKE PHARMA CO., LTD.; XI, Ning; WANG, Liang; WANG, Tingjin; WU, Weibin; (123 pag.)WO2015/175579; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 4270-27-3 ,Some common heterocyclic compound, 4270-27-3, molecular formula is C4H3ClN2O2, 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.

This compound was prepared by the method of Ishikawa et al. as described in Heterocycles 1990, 31 (9), 1641. 4-Chloro-uracil (Lancaster) (23. [36] g, 0.16 mol) was dissolved in dimethyl sulfoxide (100 [ML)] and treated with potassium carbonate [(11.] 2 g, 0.08 mol) and [1-IODOBUTANE] (Aldrich) (52.8 mL, 0.48 mol). After stirring at [23 oC] for 18 h, the reaction was then mixed with water and extracted with ethyl acetate (3X). The combined ethyl acetate layers were then washed with diluted aqueous sodium chloride solution and brine, dried (sodium sulfate) and concentrated to dryness to afford the crude product as an off-white solid (27.34 g, 85 %).

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. 4270-27-3, 6-Chloropyrimidine-2,4(1H,3H)-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2003/106459; (2003); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 941685-26-3 ,Some common heterocyclic compound, 941685-26-3, molecular formula is C12H18ClN3OSi, 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.

4-chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine (2.50 g, 8.80 mmol), compound (39c) (4.60 g) and potassium carbonate (3.10 g, 22.08 mmol) were placed in a 100 mL flask, dioxane (50 mL) and water (6 mL) were added, the reaction was stirred until homogeneous, Pd(dppf)Cl2 (370 mg) was then added, nitrogen replacement was performed for 2-3 times, and the flask was placed in an oil bath at 100C. The reaction was allowed to proceed overnight. After LC-MS indicated the substrate disappeared, insolubles were filtered off through Celite, the solvent was rotary evaporated off, and the residue was dissolved in EA, washed with water to obtain the organic phase, which was dried over anhydrous sodium sulfate, and purified by preparative flash chromatography (PE:EA=3:2), to afford compound (39d) (1.67 g, yellow solid), yield: 56%. MS m/z: 243 [M+1]+.

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. 941685-26-3, 4-Chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sichuan Kelun-Biotech Biopharmaceutical Co., Ltd.; XIE, Yinong; YOU, Zejin; DENG, Zhiwen; ZHU, Jun; WANG, Ao; FENG, Yan; LONG, Dong; ZENG, Hong; SONG, Hongmei; YE, Qijun; QI, Wei; SU, Donghai; WANG, Lichun; WANG, Jingyi; (106 pag.)EP3360878; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 3073-77-6, 2-Amino-5-nitropyrimidine, 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, 3073-77-6, blongs to pyrimidines compound. Computed Properties of C4H4N4O2

Example 51. 4-(5-Nitropyrimidin-2-ylammo)-iV-(2-hydroxyethyl)-iV- isopropylbenzamide (37); [0192] A mixture of 5-nitro-pyrimidin-2-ylamine (142 nig, 1.0 mniol), bromide intermediate 36 described in Example 50 (285 mg, 1.0 mmol), Cs2CO3 (1.4 g, 4.3 rnrnol), Xantphos (114 mg, 0.2 mmol), and Pd2(dba)3 (91 mg, 0.1 mmol) in dioxane (20 mL) was purged with argon for 5 min, and the ssuspension was heated to reflux for 2.5 hours under argon. Dioxane was removed in vacuo, and the crude mixture was adsorbed onto silica gel and purified using an Isco flash chromatography system (0% to 10% Methanol with 1% NH4OH in DCM) to afford a crude tan solid (357 mg, quant.).[0193] 1H NMR (DMSO-d6) delta 1.10 (bs, 6H), 3.54 (bs, 2H), 4.74 (bs, IH), 7.36 (d, J= 8.5 Hz, 2H), 7.82 (d, J= 8.5 Hz, 2H), 9.26 (s, 2H), 10.99 (s, IH). MS (ES+): m/z = 346 (M+H)+. LC retention time: 2.18 min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3073-77-6, its application will become more common.

Reference:
Patent; TARGEGEN, INC.; WO2006/101977; (2006); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 153286-94-3, 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 153286-94-3, name is 5-Ethynylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

[0242] Synthesis of (S)-tert-butyl (l-(3-bromo-6 pyimidin-5-ylemynyl)pyridm-2-yl)-2-(3,5- difluorophenyl)ethyl)carbamate (1G): (S)-tert-butyl (l-(3,6-dibromopyridin-2-yl)-2-(3,5- difluorophenyl)ethyl)carbamate (1G, 50 mg, 0.1 mmol) and 5-emynylpyrimidine (11.5 mg, 0.11 mmol) in THF (0.2 mL) was degassed and purged with argon. To it was added TEA (0.05 mL), Pd(PPh3)2Cl2(7 mg, 0.01 mmol) and Cul (2 mg, 0.01 mmol). The reaction was stirred for 2 hr at 40 °C and then cooled to ambient temperature. The reaction mixture was partitioned between EtOAc and 0 (plus 0.1 mL of ammonia). The organics were separated, dried, and removed in vacuo. The residue purified by column chromatography on silica to provide the title compound. MS (m/z) 516.66 [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 153286-94-3, 5-Ethynylpyrimidine.

Reference:
Patent; GILEAD SCIENCES, INC.; BRIZGYS, Gediminas; CANALES, Eda; HALCOMB, Randall, L.; HU, Yunfeng, Eric; KATO, Darryl; LINK, John, O.; LIU, Qi; SAITO, Roland, D.; TSE, Winston, C.; ZHANG, Jennifer, R.; (253 pag.)WO2016/33243; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 123148-78-7 ,Some common heterocyclic compound, 123148-78-7, molecular formula is C6H3ClIN3, 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.

Example 49; 4-Chloro-5-iodo-7-(2-trimethylsilanyl-ethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidine (49.1); To a suspension of sodium hydride (60% in mineral oil, 78.8 g, 1.97 mmol) in dry THF (15 ml_), is added a solution of intermediate 38.2 (0.50 g, 1.79 mmol) in THF (5 ml.) dropwise and the resulting mixture is stirred for 15 min. It is then cooled to O0C and SEM chloride (0.33 ml_, 1.881 mmol) is added and the reaction mixture is stirred overnight. The reaction is quenched by carefully adding aqueous NH4CI and then extracted with EtOAc. The combined organic layer is successively washed with water, brine, dried over anhydrous Na2SO4 and concentrated in vacuo. Purification of the crude residue by column chromatography (silica 100-200 mesh, hexane : ethyl acetate = 92 : 8) gives intermediate 49.1 as a white solid, m p 108-1100C. 1H NMR (400 MHz, DMSOd6): delta 8.64 (s, 1 H), 7.53 (s, 1 H), 5.61 (s, 1 H), 3.53 (d, J = 8.29 Hz, 1 H); 0.92 (d, J = 8.29 Hz, 1 H); -0.03 (s, 9H). ESI-MS: calcd. for Ci2H17CIIN3OSi (409.73); found: 410 [M+H+].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,123148-78-7, its application will become more common.

Reference:
Patent; NOVARTIS AG; CHEN, Yen-Liang; DURAISWAMY, Jeyaraj; KONDREDDI, Ravinder Reddy; YIN, Zheng; WO2010/15637; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia