Pyrimidines

Synthetic Route 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.

Step 1: 4-methyl-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine 103.6 g of 4-chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine and 2.96 g of [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium were added to 1.13 L of tetrahydrofuran, and cooled down to -15?-5 C., and then 200 mL of methylmagnesium bromide (3M dissolved in ether) was slowly added dropwise thereto. After the addition was completed, the resulting mixture was heated to 60?65 C. and reacted under reflux for 2 hours. After the reaction was completed, the temperature was lowered to -15?-5 C., and then the reaction was quenched by slowly dropwise adding 455 mL of a saturated ammonium chloride solution. The resulting mixture was filtered, the filter cake was rinsed with 455 mL of tetrahydrofuran, and then the filter cake was discarded, and the filtrate was concentrated under reduced pressure. To the residue was added 455 mL of purified water, and 1.13 L of ethyl acetate was added to extract the resulting mixture twice. The organic phases were combined and washed with 150 g of saturated brine. Then, the organic phase was concentrated under reduced pressure to distill off the solvent to obtain 103.2 g 4-methyl-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine. 1H-NMR (500 MHz, DMSO-d6): delta=8.67 (s, 1H), 7.63 (d, J=3.7 Hz, 1H), 6.70 (d, J=3.6 Hz, 1H), 5.60 (s, 2H), 3.54?3.45 (m, 2H), 2.64 (s, 3H), 0.81 (t, J=8.0 Hz, 2H), 0.12 (s, 9H); MS (ES): 264.15 (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,941685-26-3, its application will become more common.

Reference:
Patent; CHIA TAI TIANQING PHARMACEUTICAL GROUP CO., LTD.; Zhang, Xiquan; Zhang, Aiming; Zhou, Zhou; Yang, Leilei; Yao, Huadong; Zhu, Xueyan; Wang, Hubo; (29 pag.)US2019/23712; (2019); 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. 18740-38-0, name is Thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione, the common compound, a new synthetic route is introduced below. Product Details of 18740-38-0

Thieno [2,3- D] pyrimidine-2,4 (1H, 3H) -dione (0.5 g, 2.98 mmol) HMDS (1.2 g, 7.44 mmol), toluene (8 mL) was added to the reaction flask, concentrated sulfuric acid (20 mg) was added with stirring, Stirring and refluxing reaction 12h. The solvent was concentrated to dryness under reduced pressure.

The synthetic route of 18740-38-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Xunhe Pharmaceutical Technology Co., Ltd.; Zheng Yongyong; Jin Hua; Zhou Feng; Huang Meihua; Meng Xin; (28 pag.)CN107286174; (2017); A;,
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Synthetic Route of 63200-54-4, 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 63200-54-4, name is 2,4-Dichloro-5H-pyrrolo[3,2-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

Compound 1 (435 mg, 2.3 mmol), methyl o-aminobenzoate (419 mg, 2.7 mmol) were dissolved in 10 mL tertbutanol.To the solution was added trifluoroacetic acid (0.256 mL, 3.45 mmol). The resulting reaction liquid was heatedin 85C oil bath with stirring until compound 1 was reacted completely (LC-MS tracking). The reaction was stopped. Tothe reaction liquid was added 40 mL of saturated sodium bicarbonate solution, and the liquid was separated. The organicphase was washed twice with saturated sodium chloride solution, dried over anhydride sodium sulfate, concentratedand purified by silica-gel column chromatography (dichloromethane/methanol) to yield compound 4 (white solid, 424mg, yield 61%), which was used directly for the reaction in next step.MS (ESI) m/z: 303 [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 63200-54-4, 2,4-Dichloro-5H-pyrrolo[3,2-d]pyrimidine.

Reference:
Patent; Xiamen University; DENG, Xianming; ZHUANG, Zhongji; DENG, Zhou; HUANG, Xiaoxing; LIU, Yan; ZHANG, Ting; HUANG, Wei; XU, Qingyan; HU, Zhiyu; (86 pag.)EP3290420; (2018); A1;,
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Reference of 3029-64-9 ,Some common heterocyclic compound, 3029-64-9, molecular formula is C5Cl3N3, 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.

Under nitrogen protection, 6.28 g (25 mmol) of isopropyl carbazole,2.83 g (10 mmol) of 2,4,6-trichloro-5-cyanopyrimidine, 1.92 g (20 mmol) of NaOBu-t, 1.92 g (0.2 mmol) (t-Bu)3HBF4, 0.09 g (0.1 mmol) Pd2 ( Dba) 3 was added to a 250 ml three-necked flask, 100 ml of toluene was added as a reaction solvent, the temperature was raised to reflux temperature, and the mixture was stirred overnight on a magnetic stirrer. After completion of the reaction, the reaction solution was dried to dryness, and the obtained crude product was purified from petroleum ether and methylene chloride (PE: DCM = 5:1) as a mobile phase. Intermediate 1 was obtained as a white solid powder weighing 4.70 g, yield 73.7percent.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3029-64-9, its application will become more common.

Reference:
Patent; Beijing Dingcai Technology Co., Ltd.; Gu’an Dingcai Technology Co., Ltd.; Gao Wenzheng; Huang Xinxin; Ren Xueyan; (27 pag.)CN109553606; (2019); A;,
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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. 1445-39-2, name is 2-Amino-5-iodopyrimidine. A new synthetic method of this compound is introduced below., Computed Properties of C4H4IN3

Preparation Example 7 To a mixture of 2-amino-5-iodopyrimidine (1 g), 3-ethynyl-2,4-difluoro-1,5-dimethoxybenzene (897 mg), tetrakistriphenylphosphine palladium (261 mg), copper iodide (43 mg), and N,N-dimethylformamide (20 mL), N,N-diisopropylethylamine (1.55 mL) was added under an argon atmosphere followed by stirring at 80 C. for 1 hour. The reaction mixture was concentrated under reduced pressure, and to the obtained residue were added chloroform and water, and insoluble materials were removed by filtration through celite. After the filtrate was extracted with chloroform, the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and then filtered. After the filtrate was concentrated under reduced pressure, the resulting residue was purified by silica gel column chromatography (chloroform/methanol) to give 5-[(2,6-difluoro-3,5-dimethoxyphenyl)ethynyl]pyrimidin-2-amine (1.07 g).

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, 1445-39-2, 2-Amino-5-iodopyrimidine.

Reference:
Patent; KOTOBUKI PHARMACEUTICAL CO., LTD.; Astellas Pharma Inc.; Kameda, Minoru; Kuriwaki, Ikumi; Iikubo, Kazuhiko; Hisamichi, Hiroyuki; Kawamoto, Yuichiro; Moritomo, Hiroyuki; Suzuki, Tomoyuki; Futami, Takashi; Suzuki, Atsushi; Tsunoyama, Kazuhisa; Asaumi, Makoto; Tomiyama, Hiroshi; Noda, Atsushi; Iwai, Yoshinori; Tokuzaki, Kazuo; Okada, Haruki; Miyasaka, Kozo; US2014/142084; (2014); A1;,
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Synthetic Route of 1060816-67-2, 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.1060816-67-2, name is 2-Chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine, molecular formula is C7H6ClN3, molecular weight is 167.6, as common compound, the synthetic route is as follows.

Step-2: 5,5-Dibromo-2-chloro-7-methyl-5H-pyrrolo[2,3-d]pyrimidin-6(7H)-one [0183] To a solution of 2-chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine (835 mg, 5 mmol) in t-BuOH/H2O ((10 mL/3 mL) was added NBS (2.67 g, 15 mmol) and stirred for 3 h at room temperature. The reaction mixture was concentrated and dissolved in EtOAc (30 mL). The EtOAc layer was washed with NaHCO3, brine, dried (Na2SO4) and concentrated to give crude 5,5-Dibromo-2-chloro-7-methyl-5H-pyrrolo[2,3-d]pyrimidin-6(7H)-one (1.72 g) which was used for the next step.

Statistics shows that 1060816-67-2 is playing an increasingly important role. we look forward to future research findings about 2-Chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine.

Reference:
Patent; FORMA THERAPEUTICS, INC.; ASHWELL, Susan; CAMPBELL, Ann-Marie; CARAVELLA, Justin Andrew; DIEBOLD, R. Bruce; ERICSSON, Anna; GUSTAFSON, Gary; LANCIA, David R.; LIN, Jian; LU, Wei; WANG, Zhongguo; (147 pag.)WO2016/171755; (2016); A1;,
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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. 84955-31-7, name is 4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine. A new synthetic method of this compound is introduced below., Formula: C6H5ClN4

To a suspension of 2-AMINO-4- CHLORO-7H-PYRROLO [2, 3-d] pyrimidine (1) (1.0 g, 6.0 mmol) in MeOH (50 mL) and aqueous ammonium hydroxide (1 mL) was added 10% Pd-C (500 mg). The reaction mixture was stirred under atmospheric pressure for 17 h and the catalyst was filtered through A pad of Celite. The filtrate was concentrated and chromatographed with silica gel (CH2CL2 : MEOH = 90: 10) to yield 717 mg of the target compound (90%). H NMR (DMSO-D6) : 8 11.4 (bs, 1H), 8. 50 (s, 1 H), 7.11 (dd, J= 3. 6,0. 6 HZ, 1H), 6.49 (bs, 2H), 6.32 (dd, J= 3. 6,0. 9 HZ, 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, 84955-31-7, 4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine.

Reference:
Patent; RIBAPHARM INC.; WO2004/80466; (2004); A1;,
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Pyrimidine – Wikipedia

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. 213265-83-9, name is 4,6-Dichloro-5-fluoropyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Safety of 4,6-Dichloro-5-fluoropyrimidine

0.55 mL (5.99 mmol) cyclopropane methanol in 15 mL THF are charged with 0.31 g (7.19 mmol) NaH and the reaction mixture is stirred at r.t. for 10 min. Then 1.00 g (5.99 mmol) 4,6-dichloro-5-fluoro-pyrimidine are added and stirred at r.t. for 1 h. Afterwards the reaction is quenched by the addition of water and extracted with EtOAc. The organic layers are combined, washed with water (2¡Á), dried over MgSO4, filtered and the solvent is removed in vacuo.C8H8ClFN2O (M=202.6 g/mol)ESI-MS: 203 [M+H]+Rf (TLC): 0.37 (silica gel, PE/EtOAc 9/1)

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, 213265-83-9, 4,6-Dichloro-5-fluoropyrimidine.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; FLECK, Martin; HEIMANN, Annekatrin; HEINE, Niklas; NOSSE, Bernd; ROTH, Gerald Juergen; US2014/315882; (2014); A1;,
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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. 90349-23-8, name is 5,7-Dimethylpyrazolo[1,5-a]pyrimidine-3-carboxylic acid, molecular formula is C9H9N3O2, 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: 90349-23-8

(Benzotriazol-1 -yloxy)tripyrrolidinophosphonium hexafluorophosphate (980 mg, 1 .88 mmol)was added to a mixture of 5,7-dimethylpyrazolo[1 ,5-a]pyrimidine-3-carboxylic acid (300 mg,1 .57 mmol, GAS no 90349-23-8), trans-4-aminocyclohexanecarboxylate hydrochloride (274mg, 1.41 mmol, Gas No. 61367-07-5) and N-ethyl-N-isopropylpropan-2-amine (1.1 ml, 6.3mmol) in N,N-dimethylformamide (9.8 ml) and the mixture was stirred for 3 h at roomtemperature. For work-up the reaction mixuture was concentrated under reduced pressure. The residue was dissolved with dichloromethane and the organic phase was washed with water, filtrated through a silicone filter and concentrated. The crude product crystalized upon standing to give methyl trans-4-{[(5,7-dimethylpyrazolo[1 ,5-a]pyrim idin-3-yl)carbonyl]amino}cyclohexanecarboxylate (237 mg, 45% yield).LG-MS (Method 1): R = 1 .01 mm; MS (ESIneg) m/z = 329.2 [M-H]-.1HNMR (400 MHz, DMSO-d6): 6 [ppm] = 8.49 (5, 1H), 7.97 (d, 1H), 7.12 (d, 1H), 3.86-3.70(m, 1H), 3.61 (5, 3H), 2.74 (d, 3H), 2.62 (5, 3H), 2.43-2.31 (m, 1H), 2.08-1.90 (m, 4H), 1.58-1.29 (m, 4H).

With the rapid development of chemical substances, we look forward to future research findings about 90349-23-8.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; EIS, Knut; ACKERMANN, Jens; WAGNER, Sarah; BUCHGRABER, Philipp; SUeLZLE, Detlev; HOLTON, Simon; BENDER, Eckhard; LI, Volkhart; LIU, Ningshu; SIEGEL, Franziska; LIENAU, Philip; BAIRLEIN, Michaela; VON NUSSBAUM, Franz; HERBERT,Simon; KOPPITZ, Marcus; (734 pag.)WO2016/177658; (2016); A1;,
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Related Products of 14080-59-2, Adding some certain compound to certain chemical reactions, such as: 14080-59-2, name is 4-Chlorothieno[2,3-d]pyrimidine,molecular formula is C6H3ClN2S, 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 14080-59-2.

To a tetrahydrofuran (15 ml) solution of 4-chlorothieno [2,3-d] pyrimidine (200 mg, 1.17 mmol) was added 1-methylpiperazine(0.26 ml, 2.34 mmol) and sodium hydroxide(0.94 g, 2.34 mmol) was added, followed by heating under reflux for 6 hours.After distilling off the solvent of the reaction solution under reduced pressure, ethyl acetate (20 ml) was added to the residue,And distilled water (15 ml) were added and extracted.Further, the aqueous layer was extracted twice with ethyl acetate (15 ml).The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate.The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography(Hexane: ethyl acetate = 3: 1 – 1: 1)4- (4-phenyl-1-piperazinyl) -thieno [2,3-d]Pyrimidine as a brown solid (148 mg, 54%).Toluene (20 ml) and 1 N HCl aqueous solution (0.6 ml) were added to the obtained solid, and the mixture was heated under reflux for 1 hour. After cooling the reaction solution to room temperature, suction filtration was carried out,4- (4-methyl-1-piperazinyl) -thieno [2,3-d] pyrimidine hydrochloride (127 mg, 45%)As a brown solid.

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. 14080-59-2, 4-Chlorothieno[2,3-d]pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CHIBA UNIVERSITY; JUNTENDO; HOSHINO, TYUJI; YANAGITA, HIROSHI; YAMAMOTO, NORIO; (17 pag.)JP5765650; (2015); B2;,
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