Pyrimidines

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. 93366-88-2, name is 7H-Pyrrolo[2,3-d]pyrimidin-2-amine. This compound has unique chemical properties. The synthetic route is as follows. category: pyrimidines

7H-pyrrolo[2,3-d]pyrimidin-2-amine (160 mg, 1.19 mmol), 3-bromo-5-iodopyridine (676 mg, 2.39 mmol),potassium carbonate (493 mg, 3.57 mmol) and proline(28 mg, 0.24 mmol) was added to an eggplant flask, dimethyl sulfoxide was added, and the reaction solution was deoxidized. Copper iodide (23 mg, 0.12mmol) was added and the reaction solution was deoxygenated. Heat to 90 C and stir for 16 hours. After the reaction was completed, it was cooled to room temperature, water and ethyl acetate were added, and the mixture was filtered over celite. The target compound was obtained in 24 mg.

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, 93366-88-2, 7H-Pyrrolo[2,3-d]pyrimidin-2-amine.

Reference:
Patent; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Zhao Yujun; Li Zhiqiang; Yan Ziqin; Li Jia; Zhou Yubo; Su Mingbo; Chen Zheng; (138 pag.)CN109810110; (2019); A;,
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Electric Literature of 20781-06-0, 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. 20781-06-0, name is 2,4-Diaminopyrimidine-5-carboxaldehyde. A new synthetic method of this compound is introduced below.

A mixture of 0.188 g (1 mmol) of compound of formula V and 0.447 g (1.5 mmol) of compound of formula III-1, 0.126 g (2 mmol) of sodium cyanoborohydride was added and maintained in a reflux state for 24 hours in 15 mL of methanol, The water was washed with ethyl acetate and the organic phase was washed with saturated brine and the organic phase was concentrated (the solvent was removed under reduced pressure). The residue was purified by silica gel column chromatography (Eluent: methanol: dichloromethane = 1: 10, v / v) to give a white solid (IB-1) The yield was 78%

At the same time, in my other blogs, there are other synthetic methods of this type of compound,20781-06-0, 2,4-Diaminopyrimidine-5-carboxaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; East China University of Science and Technology; Zhu Jin; Huang Jin; Chen Wenhua; Yao Xue; Ling Dazheng; Wang Manjiong; Jiang Hualiang; Li Jian; (21 pag.)CN106938997; (2017); A;,
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Application of 31169-25-2, 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. 31169-25-2, name is 7-Bromothieno[3,2-d]pyrimidin-4(3H)-one, molecular formula is C6H3BrN2OS, 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.

7-Bromothieno[3,2-d]pyrimidine-4(3H)-one (5.9g) was dissolved in POCl3 (20mL) and then stirred at 150C for 3 hours. After cooling down to room temperature, the remaining POCI3 was concentrated and added to ice water to obtain a solid. The solid was washed with sat. NaHC03 solution and dried with N2 gas to obtain the title compound. NMR (400MHz, DMSO-d^) delta 9.16 (s, 1H), 8.79 (s, 1H).

According to the analysis of related databases, 31169-25-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; HANMI HOLDINGS CO., LTD.; KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY; CATHOLIC UNIVERSITY INDUSTRY ACADEMIC COOPERATION FOUNDATION; SON, Jung Beom; JUNG, Seung Hyun; CHOI, Wha Il; JUNG, Young Hee; CHOI, Jae Yul; SONG, Ji Yeon; LEE, Kyu Hang; LEE, Jae Chul; KIM, Eun Young; AHN, Young Gil; KIM, Maeng Sup; CHOI, Hwan Geun; SIM, Tae Bo; HAM, Young Jin; PARK, Dong-sik; KIM, Hwan; KIM, Dong-Wook; WO2011/93684; (2011); A2;,
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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. 4595-61-3, name is Pyrimidine-5-carboxylic acid, the common compound, a new synthetic route is introduced below. name: Pyrimidine-5-carboxylic acid

To a solution of pyrimidine-5-carboxylic acid (1.38 g, 11.13 mmol, 1.1equiv; [CAS RN 4595-61-3]) in DMF (44 mL) was added 3-(4-trifluoromethyl-phenyl)-prop-2-yn-1-ol(2.02 g, 10.1 mmol, 1.0 equiv; [CAS RN 173546-21-9]), 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide) hydrochloride (2.33 g, 12.1 mmol, 1.2 equiv; [CASRN 25952-53-8]) and 4-dimethylaminopyridine (0.25 g, 2.0 mmol, 0.2 equiv). The reaction mixturewas stirred at rt for 2 h and then concentrated by evaporation under reducedpressure. A sat. solution of NaHCO3 (50 mL) was added and the crude productextracted with DCM (3 x 100 mL). The combined organic layers were dried over MgSO4,concentrated under reduced pressure and the product purified by MPLC elutingwith a gradient of DCM / methanol. The title compound was isolated as whitesolid (2.36 g, 76percent).?1H NMR (600 MHz, CDCl3): d = 5.23 (s, 2H), 7.57 ? 7.60 (m, 4H), 9.35 (s, 2H), 9.41 (s, 1H). 13CNMR (150 MHz, CDCl3): d = 54.0, 84.5, 86.1, 123.9 (q, JCF= 270.6 Hz), 123.9 (br s), 125.5 (q, JCF= 3.7 Hz), 125.7 (d, JCF =1.4 Hz), 131.0 (q, JCF =32.6 Hz), 132.3, 158.3, 161.9, 163.1. 19F NMR (280MHz, CDCl3): d = -63.0. HRMS (ESI+): m/z [M]+ calcd for C15H9F3N2O2:306.0616, found: 306.0610.

The synthetic route of 4595-61-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Martin, Rainer E.; Lenz, Mario; Alzieu, Thibaut; Aebi, Johannes D.; Forzy, Liliane; Tetrahedron Letters; vol. 54; 49; (2013); p. 6703 – 6707;,
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Synthetic Route of 1152475-42-7, 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 1152475-42-7, name is 7-Bromo-2-chlorothieno[3,2-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

Compound 1-h (671 mg, 1.64 mmol), 2-(methanesulfonyl)phenylboronic acid (328 mg, 1.64 mmol), bis(triphenylphosphine)palladium(II) dichloride (69 mg, 0.09 mmol) 2-di-tert-butylphosphino- 2?,4?,6?-triisopropylbiphenyl (63 mg,0.15 mmol) and 2 M aqueous sodium carbonate solution (6.5 mL, 13 mmol) were dissolved in 1,4-dioxane (13 mL). Thereaction mixture was replaced with nitrogen three times to remove the oxygen inside the system and then heated at90C for 6 hours. The reaction was cooled to room temperature, diluted with ice water (100 mL) and extracted withdichloromethane (100 mL 3 3). The combined organic phases were washed successively with water (50 mL 3 3) andbrine (50 mL),dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure.The residue was purified by silica gel thin layer chromatography preparative plate (dichloromethane: methanol = 40: 1)to deliver a yellow solid 5-b (130 mg, yield: 24%). LC-MS (ESI): m/z = 325 [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 1152475-42-7, 7-Bromo-2-chlorothieno[3,2-d]pyrimidine.

Reference:
Patent; Guangzhou Maxinovel Pharmaceuticals Co., Ltd.; ZHANG, Nong; XU, Zusheng; WANG, Tinghan; WANG, Yuguang; (99 pag.)EP3287463; (2018); A1;,
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Related Products of 90213-67-5, 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 90213-67-5, name is 2,4-Dichloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Sonogashira Coupling; Compound 2a: A solution of 1(400 mg, 1.98 mmol) in anhyd Et3N (20 mL) was flushed withargon and Pd(PPh3)2Cl2 (28.0 mg, 0.04 mmol), PPh3 (21.0 mg,0.08 mmol), CuI (3.8 mg, 0.02 mmol) and phenylacetylene (260muL, 2.38 mmol) were added. The mixture was stirred underargon at 60 C for 2-3 h. After cooling, the reaction mixture waspoured into H2O (40 mL) and extracted with CHCl3. The extractwas dried over Na2SO4, filtered and the solvent removed byrotary evaporation. The residue was purified by column chromatography(eluent CHCl3) and recrystallized to give compound 2a.

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 90213-67-5, 2,4-Dichloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine.

Reference:
Article; Bucevicius, Jonas; Tumkevicius, Sigitas; Synlett; vol. 26; 6; (2015); p. 810 – 814;,
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Related Products of 15783-48-9, 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 15783-48-9, name is 2,4-Dichlorofuro[3,4-d]pyrimidin-7(5H)-one. This compound has unique chemical properties. The synthetic route is as follows.

2,6-Dihydroxypyrimidine-4-carboxylic acid (100 g, 73.4 mmol) and paraformaldehyde (84 g, 293 mmol) were combined with concentrated HCl (1.5L) and heated to reflux at 85-95 C for 18 hours. The reaction was then cooled and HCl was evaporated under reduced pressure to obtain a solid. The solid was washed with petrolium ether to give crude 2,4-dihydroxyfuro[3,4- d]pyrimidin-7(5H)-one (90 g, 83 % yield) which was used next tep without further purification.[0113] A mixture of 2,4-dihydroxyfuro[3,4-d]pyrimidin-7(5H)-one (lOOg, 595mmol), phosphoryl trichloride (800mL) and N,N-diethylaniline (150 mL) was heated at 110 C for 18 hours. The reaction was cooled to ambient temperature, the solvent was removed in vacuo to give a residue. The residue was purified on a silica gel column eluted with petroliumether_EtOAc=5: l to give 2,4-dichlorofuro[3,4-d]pyrimidin-7(5H)-one (70 g, 57 % yield) as an off-white solid.[0114] A solution of 2,4-dichlorofuro[3,4-d]pyrimidin-7(5H)-one (34g, 165mmol) in DCM (770 mL) was added 8-oxa-3-azabicyclo[3.2.1]octane hydrochloride (24 g, 165 mmol) was cooled to 0 C and then triethylamine (96 mL, 660mmol) was added dropwise. The mixture was then concentrated in vacuo to give a residue which was purified on a silica gel column eluted with DCM_EtOAc=l :2 to give 4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-2-chlorofuro[3,4-d]pyrimidin- 7(5H)-one (28 g, 82% yield) as a yellow solid. MS [M+H] found 282.[0115] Under a nitrogen at 0 titanium chloride triisopropoxide (1 M in hexanes) (75 ml, 75 mmol) was added to a solution of 4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-2-chlorofuro[3,4- d]pyrimidin-7(5H)-one (19 g, 68 mmol) in THF (100 mL) followed by dropwise addition of ethylmagnesium bromide (1 M in THF) (150 ml, 150 mmol). The reaction was warmed up to ambient temperature and stirred overnight and then quenched by addition of a saturated NH4C1 solution (200 mL). The water layer was extracted with ethyl acetate, and the combined organic layers were dried over Na2S04, filtered, and evaporated in vacuo to give a residue. The residue was purified on a silica gel column eluted with petrolium ether_EtOAc=3: l to give l-(6-(8-oxa- 3-azabicyclo[3.2.1 ]octan-3-yl)-2-chloro-5-(hydroxymethyl)pyrimidin-4-yl)cyclopropanol (5 g, 24% yield) as a yellow solid. MS [M+H] found 312.[0116] To a solution of l-(6-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-2-chloro-5- (hydroxymethyl)pyrimidin-4-yl)cyclopropanol (3 g, 9.6 mmol) and PPh3(2.5 g,14.4 mmol) in dry THF (200 mL) was added DEAD (3.77 g,14.4 mmol) dropwise at 0 C. The mixture was stirred at ambient temperature for 3 hours. The solvent was removed in vacuum to give a residue which was purified on silica gel column eluted with petroleum ether_EtOAc=4: l to give a residue which was further purified by Prep HPLC (Column: Fuji CI 8 (300×25); Wavelength 220 nm; Mobile phase: A MeCN (0.1% TFA); B water (0.1% TFA); Flow rate: 25 mL /min; Injection volume: 2 mL; Run time: 20 min; Equilibration: 3 min) to give 4′-(8-oxa-3- azabicyclo[3.2.1 ]octan-3-yl)-2′-chloro-5’H-spiro[cyclopropane- 1 ,7′-furo[3,4-d]pyrimidine] (330mg, 12% yield). MS [M+H] found 294.[0117] A mixture of 4′-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-2′-chloro-5’H-spiro[cyclopropane- l,7*-furo[3,4-d]pyrimidine] (10.2 mg, 0.035 mmol), l-Methyl-3-[4-(4,4,5,5-Tetramethyl-l,3,2- dioxaborolane-2-yl)phenyl]-urea (19.18 mg, 0.069 mmol), sat. NaHC03 aq. (0.25 ml, 0.035 mmol) and PdCl2(dppf)-CH2Cl2 (2.269 mg, 2.78 muiotaetaomicron) in 1 ,4-Dioxane (0.5 ml) was heated by microwave at 110 C for 30 min. The mixture was passed throught filter and washed with MeOH. The filtrate was purified by preparative HPLC (gradient 20-45% ACN (containing 0.035% TFA) in water (containing 0.05% TFA). The fractions containing the desired compound were combined and concentrated in vacuo to give a solid. This solid was partitioned between EtOAc and NaHC03 aq. The phases were separated and the aqueous phase was extracted with EtOAc. The combined organic phases were washed with saturated aqueous NaCl, dried and concentrated in vacuo to give a beige solid, which was triturated with hexane/ethyl acetate (1 : 1), collected by filtration, rinsed with hexane/ethyl acetate (1 :1) and dried to give the title compound (10.1 mg, 0.025 mmol, 71.4 % yield) as a beige solid. 1H NMR (400 MHz, DMSO- 6) delta ppm 1.09 (m, 2 H) 1.18 (m, 2 H) 1.78 (m, 4 H) 2.65 (s, 3 H) 3.25 (m, 2 H) 3.95 (m, 2 H) 4.43 (m, 2 H) 5.32 (s, 2 H) 6.12 (br s, 1 H) 7.47 (d, J=8 Hz, 2 H) 8.14 (d, J= 8 Hz, 2 H) 8.81 (s, 1 H). MS [M+H] found 408.

According to the analysis of related databases, 15783-48-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; JIN, Bohan; LARDY, Matthew; ZHOU, Feng; DONG, Qing; WO2012/99581; (2012); A1;,
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Application of 5305-40-8, 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.5305-40-8, name is 4,6-Dichloropyrimidine-5-carbaldehyde, molecular formula is C5H2Cl2N2O, molecular weight is 176.9882, as common compound, the synthetic route is as follows.

Preparation of 4-Chloro-1H-pyrazolo[3,4-d]pyrimidine: 4,6-Dichloro-pyrimidine-5-carbaldehyde hydrazine (10 mL, excess), and dioxane (90 mL) are combined at -78 C. in THF. The reaction solution is warmed to rt and stirred for 16 hr. The solvent is evaporated in vacuo to provide a crude residue which is diluted with dichloromethane (600 mL). The organic solution is washed with water (50 mL), brine (50 mL) and dried over anhydrous sodium sulfate. The solvent is removed in vacuo to provide 4-Chloro-1H-pyrazolo[3,4-d]pyrimidine as a yellow powder which is used without further purification.

The chemical industry reduces the impact on the environment during synthesis 5305-40-8, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ChemoCentryx, Inc.; US2007/10523; (2007); A1;,
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Related Products of 39906-04-2 ,Some common heterocyclic compound, 39906-04-2, molecular formula is C5H5Cl2N3, 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 mixture of 4,6-dichloro-2-methylpyrimidin-5amine(1 g, 5.62 mmol) and O-ethyl carbonisothiocyanatidate(0.66 ml., 5.62 mmol) was added toluene (2 mL) to wet thesolids completely. The mixture was placed on 1000 C. oil bathfor 1.5 hours, at which time, the mixture had seized to give asolid mass. The solids were cooled to ambient temperatureand triturated with ether, then the resulting solids were collectedby filtration to give ethyl 7-chloro-5-methylthiazolo[5,4-d]pyrimidin-2-ylcarbamate (1.08 g, 3.96 mmol, 70.5%yield).

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. 39906-04-2, 4,6-Dichloro-2-methylpyrimidin-5-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; COOK II, JAMES H; MCDONALD, IVAR M; KING, DALTON; OLSON, RICHARD E; WANG, NENGHUI; IWUAGWU, CHRISTIANA I; ZUSI, F.CHRISTOPHER; MACOR, JOHN E; (330 pag.)JP5714745; (2015); B2;,
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Synthetic Route of 1004-39-3 ,Some common heterocyclic compound, 1004-39-3, molecular formula is C4H6N4S, 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.

EB1 Schiff base was synthesized by reaction of 30mL of ethanol hot solution (60 C) of bisaldehyde (2,2?-(ethane-1,2-diylbis(oxy))dibenzaldehyde) (1 g, 3.7¡Á10-3mole) and 30 mL hot ethanol solution (60 C) of (hydrazine carbothioamide) (0.674 g, 7.4¡Á10-3mole) in ratio (1:2). In preparation of L1 Schiff base 30 mL of ethanol hot solution (60 C) of bisaldehyde (2,2?-(ethane-1,2-diylbis(oxy))dibenzaldehyde) (1 g, 3.7¡Á10-3mole) was mixed with 30 mL hot ethanol solution (60 C) (4,6-diaminopyrimidine-2-thiol) (0.525 g, 3.6¡Á10-3mole) in ratio (1:1). Then sulfuric acid was added to eliminate water through condensation, and then the reaction mixture was left under reflux for 2 h. The formed solid Schiff?s bases were separated by filtration and purified by crystallization from ethanol. This preparation can be summarized in the following Scheme 1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1004-39-3, its application will become more common.

Reference:
Article; Zayed, Ehab M.; Zayed; El-Desawy; Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy; vol. 134; (2015); p. 155 – 164;,
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