Pyrimidines

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.1260088-72-9, name is 2,4-Dichloro-7,7-dimethyl-5,7-dihydrofuro[3,4-d]pyrimidine, molecular formula is C8H8Cl2N2O, molecular weight is 219.0679, as common compound, the synthetic route is as follows.Safety of 2,4-Dichloro-7,7-dimethyl-5,7-dihydrofuro[3,4-d]pyrimidine

General procedure: A mixture of 2,4-dichloro-7,7-dimethyl-5,7-dihydrofuro[3,4-d]pyrimidine7 (257mg, 1.173 mmol), 1H-pyrazolo[4,3-c]pyridin-3-amine (291 mg, 1.735 mmol), N,N-diisopropylethylamine (0.40 mL, 2.3 mmol) and N,N-dimethylformamide (4.0 mL) was heated at 70 C for 2 hours. The reaction mixture was diluted with ethyl acetate, washed with water (2x) and brine, dried over magnesium sulfate, filtered, and evaporated in vacuo. The crude product was purified via flash chromatography on silica gel (24 silica, solvent gradient: 0-100% ethyl acetate in dichloromethane followed by 10% methanol indichloromethane) to yield 176.7 mg of the title compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1260088-72-9, 2,4-Dichloro-7,7-dimethyl-5,7-dihydrofuro[3,4-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Article; Hanan, Emily J.; Baumgardner, Matt; Bryan, Marian C.; Chen, Yuan; Eigenbrot, Charles; Fan, Peter; Gu, Xiao-Hui; La, Hank; Malek, Shiva; Purkey, Hans E.; Schaefer, Gabriele; Schmidt, Stephen; Sideris, Steve; Yen, Ivana; Yu, Christine; Heffron, Timothy P.; Bioorganic and Medicinal Chemistry Letters; vol. 26; 2; (2016); p. 534 – 539;,
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Adding a certain compound to certain chemical reactions, such as: 63558-65-6, 4-Chloro-5-iodopyrimidine, 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, Product Details of 63558-65-6, blongs to pyrimidines compound. Product Details of 63558-65-6

To a vial containing a solution of 4-chloro-5-iodopyrimidine (0.200 g, 0.832 mmol) in DMF (1.333 mL) was added morpholine (0.291 mL, 3.33 mmol) followed by cesium carbonate (0.542 g, 1.664 mmol). The vial was sealed with a Teflon cap and heated at 90C for 80 min, then allowed to cool to room temperature. The reaction mixture was filtered through a disposable fritted funnel and the filter cake washed with CH2CI2. The filtrate was concentrated, then further dried under high vacuum.Intermediate 105A: MS (ESI) : m/z = 292.0 [M+H]+ HPLC Peak ret. T = 1.23 minutes was product. (HPLC conditions: Column:Luna C18 4.6x30mm 3u A: 10:90 H20:ACN NH4OAc/B: 10:90 H20:ACN NH4OAc; 0%-95%B in 2 min; 4mL/min flow).

The synthetic route of 63558-65-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; VELAPARTHI, Upender; FRENNESSON, David B.; SAULNIER, Mark G.; AUSTIN, Joel F.; HUANG, Audris; BALOG, James Aaron; VYAS, Dolatrai M.; WO2012/9510; (2012); A1;,
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Pyrimidine – Wikipedia

Related Products of 61727-33-1, 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 61727-33-1 as follows.

(0234) To a solution of 5-chloro-2-(methylthio)pyrimidine-4-carboxylic acid (1.026 g, 5.02 mmol) in 1:1 DCM:methanol was added a solution of trimethylsilyldiazomethane (2M/hexanes, 1.6 mL, 3.2 mmol). The reaction was stirred at RT for 30 min and then concentrated to give the desired 29-1, which was used without further purification. MS (ESI): mass calcd. for C7H7ClN2O2S, 218.0; m/z found 219.1 [M]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,61727-33-1, its application will become more common.

Reference:
Patent; Sunesis Pharmaceuticals, Inc.; HANSEN, Stig; ERLANSON, Dan; CANCILLA, Mark; EP2257637; (2015); B1;,
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Pyrimidine – Wikipedia

Reference of 1004-39-3, 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. 1004-39-3, name is 4,6-Diaminopyrimidine-2-thiol. A new synthetic method of this compound is introduced below.

To a suspension of commercially available 4,6-diaminopyrimidine-2-thiol (5g, 35mmol) in methanol (7OmL) is added IN sodium hydroxide (35mL). The resulting solution is stirred for Ih at rt then evaporated to give a tan solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1004-39-3, 4,6-Diaminopyrimidine-2-thiol, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/22185; (2009); A2;,
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Pyrimidine – Wikipedia

Application of 90213-66-4 ,Some common heterocyclic compound, 90213-66-4, molecular formula is C6H3Cl2N3, 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.

NaH (1.1 equiv) was slowly added at 0C to a 2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine (1 equiv) solution in THF. The reaction mixture was stirred at 0C for 0.5h. p-Toluensulfonyl chloride (1 equiv) was then added and it was stirred at 0C for 4h. The solvent was evaporated to dryness, and the crude product was diluted with H2O and extracted thrice with CH2Cl2. The organic layer was washed with brine, dried over anhydrous Na2SO4, and filtered. The filtrate was concentrated to obtain the crude product for the next step.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,90213-66-4, its application will become more common.

Reference:
Article; Wang, Ruifeng; Chen, Yixuan; Zhao, Xiangxin; Yu, Sijia; Yang, Bowen; Wu, Tianxiao; Guo, Jing; Hao, Chenzhou; Zhao, Dongmei; Cheng, Maosheng; European Journal of Medicinal Chemistry; vol. 183; (2019);,
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Pyrimidine – Wikipedia

Electric Literature of 57489-77-7, 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. 57489-77-7, name is 5,7-Dichloropyrazolo[1,5-a]pyrimidine. A new synthetic method of this compound is introduced below.

To a solution of 58.3 (5.0 g, 26.59 mmol, 1.0 eq) in acetonitrile (50 mE), were added N-Iodo-succinimide (7.17 g, 31.90 mmol, 1.2. eq) at 00 C. The reaction mixture was stirred at room temperature for overnight. After completion of reaction, reaction mixture was transferred to ice cold water and product was extracted with dichloromethane. Organic layer was combined, washed with brine solution, dried over sodium sulphate and concentrated under reduced pressure to obtain crude material. This was further purified by 20% ethyl acetate in hexane to obtain 58.4. (3.7 g, Yield:44.32%). MS (ES): mlz 314.86 [M+H].

At the same time, in my other blogs, there are other synthetic methods of this type of compound,57489-77-7, 5,7-Dichloropyrazolo[1,5-a]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Nimbus Lakshmi, Inc.; Masse, Craig E.; Greenwood, Jeremy Robert; Mondal, Sayan; Cowen, Scott D.; McLean, Thomas H.; (624 pag.)US2019/31664; (2019); A1;,
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Application of 90213-67-5 , The common heterocyclic compound, 90213-67-5, name is 2,4-Dichloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine, molecular formula is C7H5Cl2N3, 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.

(2S,3S)-Ethyl 3-aminobicyclo[2.2.2]octane-2-carboxylate hydrochloride (1.26 g, 5.40mmol) and 2,4-dichloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine (1.10 g, 5.40 mmol) weredissolved in DMF (5 mL), then K2C03 (1.50 g, 11.00 mmol) was added. The mixture was stirredat rt overnight. The reaction was stopped, and water (50 mL) was added to quench the reaction,and the resulting mixture was extracted with EtOAc (50 mL x 2). The combined organic phaseswere washed with saturated brine (80 mL), dried over anhydrous Na2S04, filtered, and thefiltrate was concentrated in vacuo. The residue was purified by silica gel chromatograph(PE/EtOAc (v/v) = 1011) to give the title compound as a yellow solid (979 mg, 50%).MS (ESI, pos.ion) m/z: 363.2 [M+Ht;1H NMR (400 MHz, CDCb) 8 (ppm): 6.87 (d, J = 3.4 Hz, 1H), 6.41 (s, 1H), 5.32 (s, 1H), 4.63 (s,1H), 4.21 (q, J = 7.1 Hz, 2H), 3.76 (s, 3H), 2.39 (d, J = 4.9 Hz, 1H), 1.96- 1.52 (m, 10H), 1.26(t, J = 7.0 Hz, 3H).

The synthetic route of 90213-67-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; TANG, Changhua; REN, Qingyun; YIN, Junjun; YI, Kai; LEI, Yibo; WANG, Yejun; ZHANG, Yingjun; (303 pag.)WO2018/108125; (2018); A1;,
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Synthetic Route of 1235450-86-8, 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. 1235450-86-8, name is 5-Bromo-2-ethylpyrimidine-4-carboxylic acid, molecular formula is C7H7BrN2O2, 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.

A mixture of xylenes (50 mL) solution of 5-bromo-2-ethyl-4-carboxylic acid (5.6g, 24.3mmol) was refluxed for 2 hours. After cooling, the mixture directly applied to a silica column, petroleum ether, then compound 0601-121 eluting with ethyl acetate (5%) in petroleum ether as a yellow liquid (1.7 g, 38%).

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 1235450-86-8, 5-Bromo-2-ethylpyrimidine-4-carboxylic acid.

Reference:
Patent; CURIS INCORPORATED; CAI, XIONG; ZHAI, HAIXIAO; LAI, CHENG-JUNG; QIAN, CHANGGENG; (290 pag.)JP2015/187145; (2015); A;,
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Electric Literature of 4595-59-9, Adding some certain compound to certain chemical reactions, such as: 4595-59-9, name is 5-Bromopyrimidine,molecular formula is C4H3BrN2, 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 4595-59-9.

A suspension of 3-amino-6-cyclopropylpyridine-2-carboxylic acid ethyl ester (763 mg, 3.7 mmol), 5-bromopyrimidine (823 mg, 5.2 mmol), water (140 mul, 7.8 mmol) and potassium carbonate (920 mg, 6.7 mmol) in o-xylene (10 ml) was evacuated and vented with argon. Palladium(II) acetate (33 mg, 0.15 mmol,) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (xantphos; 107 mg, 0.18 mmol) were consecutively added under inert gas atmosphere and the reaction mixture was heated to 140 C. and stirred overnight. After cooling-down to ambient temperature, the reaction mixture was diluted with dichloromethane (15 ml) and filtrated. The filtrate was concentrated in vacuo and the product was purified by silica gel chromatography using a heptane /ethyl acetate gradient to yield the title compound (796 mg, 75.7%) as light yellow solid. MS: M=285.3 (M+H)+

According to the analysis of related databases, 4595-59-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bleicher, Konrad; Flohr, Alexander; Groebke Zbinden, Katrin; Gruber, Felix; Koerner, Matthias; Kuhn, Bernd; Peters, Jens-Uwe; Sarmiento, Rosa Maria Rodriguez; US2011/306589; (2011); A1;,
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Application of 3764-01-0, 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. 3764-01-0, name is 2,4,6-Trichloropyrimidine. A new synthetic method of this compound is introduced below.

To a solution of 2,4,6-trichloropyrimidine (0.29 mL, 2.5 mmol) in THF (5 mL) wereadded palladium acetate (8 mg, 0.035 mmol), triphenylphosphine (18 mg, 0.065 mmol),benzeneboronic acid (0.20 g, 1.6 mmol) and aqueous sodium carbonate solution (1 M, 3.3 mL,3.3 mmol). The mixture was stirred at 60 oc for 6 h under nitrogen protection. After the reactionwas completed, the mixture was cooled to rt, and concentrated in vacuo. To the residue wasadded H20 (10 mL), and the mixture was extracted with ethyl acetate (10 mL x 3). Thecombined organic layers were washed with saturated brine (10 mL), dried over anhydroussodium sulfate, filtered and concentrated. The residue was purified by silica gel columnchromatography (PE) to give the title compound as a white solid (0.225 g, 61 % ).MS (ESI, pos. ion) m/z: 225.0 [M+Ht;1H NMR (400 MHz, CDCh) 8 (ppm): 8.15-8.04 (m, 2H), 7.70 (s, 1H), 7.63-7.50 (m, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,3764-01-0, 2,4,6-Trichloropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; TANG, Changhua; REN, Qingyun; YIN, Junjun; YI, Kai; LEI, Yibo; WANG, Yejun; ZHANG, Yingjun; (303 pag.)WO2018/108125; (2018); A1;,
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Pyrimidine – Wikipedia