Tag: M.W:100-200

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

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

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 99586-66-0 ,Some common heterocyclic compound, 99586-66-0, molecular formula is C6H5ClN4, 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: d) At rt, a solution of intermediate Xl (1 eq.) and an aryl halogenide VIII (1 to 2.5 eq.) in alcohol (nBuOH or EtOH, 0.08M to 0.1M) was treated with DIPEA (2 to Seq.) and irridiated in a microwave reactor or heated in an oil bath at 120-160C for 0.5 h to 6 d. Purification of intermediates and final products IX was carried out by flash chromatography,HPLCorSFC.

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. 99586-66-0, 2-Amino-4-chloro-6-methylpyrimidine-5-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; DU, Zhenxing; HINTERMANN, Samuel; HURTH, Konstanze; JACQUIER, Sebastien; LEHMANN, Hansjoerg; MOEBITZ, Henrik; SOLDERMANN, Nicolas; STOJANOVIC, Aleksandar; WO2015/10641; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 4316-98-7, 6-Chloro-4,5-diaminopyrimidine, 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, Computed Properties of C4H5ClN4, blongs to pyrimidines compound. Computed Properties of C4H5ClN4

8-(4-((1H-pyrazol-1-yl)methyl)benzyl)-6-chloro-7H-purineCombined 2-[4-(1H-pyrazol-1-ylmethyl)phenyl]acetic acid (Fichert, Thomas; Yazdanian, Mehran; Proudfoot, John R. Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, 4 p. 719-722)(400.00 mg; 1.85 mmol; 1.00 eq.) and 6-chloropyrimidine-4,5-diamine (267.42 mg; 1.85 mmol; 1.00 eq.) in POCl3 (5.00 ml). Heated the reaction to 90 C. for 3 hours. Let the reaction cool to rt. Concentrated. Diluted with water, neutralized with sat?d NaHCO3, and extracted with ethyl acetate. Combined organics, dried with MgSO4, filtered, and concentrated. Purified by Biotage silica gel column to afford 8-(4-((1H-pyrazol-1-yl)methyl)benzyl)-6-chloro-7H-purine (319 mgs; 53%). MS (M+H)+ found for C16H13ClN6 : 325.0.

The synthetic route of 4316-98-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Global Blood Therapeutics, Inc.; Li, Zhe; Xu, Qing; Yu, Chul; Yee, Calvin; Gwaltney,, II, Stephen L.; Metcalf, Brian W.; Richards, Steven; Lardy, Matthew A.; Setti, Lina; Sham, Hing; US2015/315198; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 13036-57-2, 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.13036-57-2, name is 2-Chloro-4-methylpyrimidine, molecular formula is C5H5ClN2, molecular weight is 128.56, as common compound, the synthetic route is as follows.

Step E: 2-Propen-1-yl [3-[(2-chloro-4-pyrimidinyl)acetyl]-2-(methyloxy)phenyl]carbamate; To a solution of methyl 2-(methyloxy)-3-{[(2-propen-1-yloxy)carbonyl]amino}benzoate (123 g, 464 mmol,) in dry THF (800 mL) at -10 C., LiHMDS (1M in THF, 1440 mmol, 1440 mL) was added dropwise and the solution was allowed to stir for 1 h at 0 C. A solution of 2-chloro-4-methylpyrimidine (72 g, 560 mmol) in THF (150 mL) was then added dropwise to the solution of ester and base at 0 C. over 20 min. The solution was allowed to stir 1 h at rt. TLC showed the reaction was complete. The reaction was quenched by addition of the saturated aqueous NH4Cl (800 mL) at 0 C. The reaction mixture was extracted with EtOAc (1 L×3). The combined organic layers were washed with water and brine successively, dried over Na2SO4, filtered and concentrated under reduced pressure to give the crude product, which was purified by flash column on silica gel, eluting with DCM. This solution was evaporated to obtain a solid. The orange solid was triturated with a small amount of EtOAc and filtered, rinsing with diethyl ether to give the title compound of Step E (109.9 g, 67.8% yield). 1H NMR (400 MHz, CDCl3) delta ppm 13.64-13.68 (br, 1H), 8.38 (d, J=5.3 Hz, 1H), 8.15-8.21 (m, 1H), 7.31-7.39 (m, 2H), 7.15-7.18 (m, 1H), 6.87 (d, J=5.3 Hz, 1H), 6.19 (s, 1H), 5.92-6.15 (m, 1H), 5.23-5.40 (m, 2H), 4.66-4.70 (m, 2H), 3.76 (s, 3H).

The chemical industry reduces the impact on the environment during synthesis 13036-57-2, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Adams, Jerry Leroy; Dickerson, Scott Howard; Johnson, Neil W.; Kuntz, Kevin; Petrov, Kimberly; Ralph, Jeffrey M.; Rheault, Tara Renae; Schaaf, Gregory; Stellwagen, John; Tian, Xinrong; Uehling, David Edward; Waterson, Alex Gregory; Wilson, Brian; US2009/298815; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 5305-59-9 , The common heterocyclic compound, 5305-59-9, name is 6-Chloropyrimidin-4-amine, molecular formula is C4H4ClN3, 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 3-chloro-4-(3-fluorobenzyloxy)aniline (5.00 g, 19.86 mmol) and compound 2 (4.17 g, 16.55 mmol) with two drops concd HCl in n-BuOH (30 mL) was heated at 110 C and kept stirring for 3 h. As the mixture cooled, the formed yellow solid was filtered through washing with n-BuOH followed by saturated NaHCO3 aqueous solution. After being dried overnight at vacuum drying oven at 40 C, the solid was purified by column chromatography on silica gel eluted with EtOAc/petroleum ether (1:2) to give 3 as a yellowish green solid (6.18 g, 13.24 mmol, 80% yield).

The synthetic route of 5305-59-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Li, Siyuan; Guo, Chunying; Zhao, Hongli; Tang, Yun; Lan, Minbo; Bioorganic and Medicinal Chemistry; vol. 20; 2; (2012); p. 877 – 885;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 4316-94-3, 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 4316-94-3, name is 6-Chloro-5-nitropyrimidin-4-amine. This compound has unique chemical properties. The synthetic route is as follows.

2-[4-(4-Trifluoromethylpyridin-2-yloxy)-phenyl]-ethanol (product from Step 1; 400 mg, 1.4 mmol) was dissolved in DMSO (10 mL), treated with 95% NaH (36 mg, 1.5 mmol) and the mixture was warmed to 50-600C to produce a clear solution. Upon cooling the mixture was treated with 4-amino-5-nitro-6-chloropyrimidine (260 mg, 1.5 mmol) and heated at 450C for 6 h. After cooling the mixture was poured into H2O (60 mL) and the precipitate was collected by suction filtration, washed with H2O and air-dried on the filter: 1H NMR (300 MHz, CDCl3) delta 8.39 (s, IH), 8.33 (s, IH), 8.18 (s, IH), 7.38 (m, 2H), 7.15 (m, 4H), 4.69(t, / = 6.8 Hz, 2H), 3.15 (t, 6.6 Hz, 2H). This material was used in the next step without further purification.

According to the analysis of related databases, 4316-94-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DOW AGROSCIENCES LLC; BREWSTER, William; DEMETER, David; ERICKSON, W.; LOWE, Christian; KLITTICH, Carla; NUGENT, Jaime; RIEDER, Brent; SIDDALL, Thomas; YAO, Chenglin; YERKES, Carla; ZHU, Yuanming; WO2011/25505; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia