Pyrimidines

Synthetic Route of 65996-50-1, 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.65996-50-1, name is 1H-Pyrrolo[3,2-d]pyrimidine-2,4(3H,5H)-dione, molecular formula is C6H5N3O2, molecular weight is 151.12, as common compound, the synthetic route is as follows.

5.1.1.2 2,4-Dichloropyrrolo[3,2-d]pyrimidine (1) To pyrrolo[3,2-d]pyrimidin-2,4-dione 5 (2.00 g, 13.2 mmol), 1 N NaOH (15 mL), and 0.60 g NaOH in 15 mL H2O was added and the mixture stirred at 40 C until a clear solution was obtained. The solution was cooled to room temperature (21-25 C) and then placed in an ice bath to obtain thick slurry. The slurry was then filtered to obtain a pale yellow solid. The solid was dissolved in 1 N NaOH (15 mL), and heated to 40 C to obtain a clear solution that upon cooling provided white crystals. The crystals were washed with MeOH (20 mL) and acetone (20 mL), and then dried under vacuum. The dry solids were taken in phenylphosphonic dichloride (10 mL) and heated to 170-175 C for 5 h during which the reaction mixture became a brown-black solution. After 5 h the hot reaction mixture was poured onto ice, extracted with EtOAc (200 mL) and the organic layer washed with satd NaHCO3 solution (3* 100 mL) till all effervescence subsided. The organic layer was then washed with brine and dried over MgSO4. The organic layer was concentrated in vacuo and loaded onto silica. The product was purified using column chromatography eluting with 9:1 then 3:1 hexanes/EtOAc to obtain 1 as an off-white solid (1.50 g, 7.9 mmol, 60%). Rf 0.5 in 3:1 hexanes/EtOAc. Mp 228.3-232.0 C. 1H NMR (400 MHz, DMSO-d6): delta 6.71 (d, 1H, J = 3.2 Hz), 8.09 (d, 1H, J = 2.8 Hz), 12.75 (s, 1H, NH). 13C NMR (100 MHz, DMSO-d6): delta 103.2, 124.3, 138.0, 143.5, 149.6, 153.9. ESI-MS m/z for C6H3Cl2N3 calculated [M+H]+ 187.9776, found 187.9777.

Statistics shows that 65996-50-1 is playing an increasingly important role. we look forward to future research findings about 1H-Pyrrolo[3,2-d]pyrimidine-2,4(3H,5H)-dione.

Reference:
Article; Temburnikar, Kartik W.; Ross, Christina R.; Wilson, Gerald M.; Balzarini, Jan; Cawrse, Brian M.; Seley-Radtke, Katherine L.; Bioorganic and Medicinal Chemistry; vol. 23; 15; (2015); p. 4354 – 4363;,
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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 54326-16-8, name is 5-Chloropyrimidin-2(1H)-one. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 5-Chloropyrimidin-2(1H)-one

EXAMPLE 3 1(4-Chlorophenylsulfinyl)methyl-5-chloropyrimidin-2-one Potassium tert-butoxide (4 mmol) in DMF (10 ml) was added to a solution of 5-chloropyrimidin-2-one (4 mmol) in DMF (40 ml). The mixture was stirred at room temperature for 10 min before 1-bromomethyl-sulfinyl-4-chlorobenzene (see Preparation 5) (4 mmol) was added. The resultant mixture was stirred at 60 C. for 2 days, the solvent distilled off at reduced pressure, the residue triturated with water, the insoluble material dried and washed with a little chloroform before recrystallization from DMSO; the crystalline material was also washed with a little methanol and finally with water; yield 0.30 g (25%), m.p. 262 C. (Found: C43.63; H2.68. Calc. for C11 H8 Cl2 N2 O2S: C43.59; H2.67) 1 H NMR (DMSO-d6); delta 5.12 (CH2), 7.60 (Ph, b.s.), 8.19 and 8.62 (H-4, H-6, d, J 4 Hz). IR (KBr): 1660 (CO), 1060 cm–1 (SO). MS (70 eV; m/e (rel. int. %): 302 (0.5, M), 159 (6), 145 (33), 143 (100).

With the rapid development of chemical substances, we look forward to future research findings about 54326-16-8.

Reference:
Patent; Nyegaard & Co. A.S.; US4596870; (1986); A;,
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Adding a certain compound to certain chemical reactions, such as: 62802-42-0, 2-Chloro-5-fluoropyrimidine, 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, 62802-42-0, blongs to pyrimidines compound. COA of Formula: C4H2ClFN2

General procedure: Under nitrogen, a solution of sodium carbonate (4.24g, 40 mmol) in water (20 mL) was added to asolution of 2-chloro-5-fluoropyrimidine 4 (2.47 mL, 20 mmol) in toluene (60 mL), and the mixture washeated to 80 C. Bis(triphenylphosphine)palladium(II) chloride (701.9 mg, 1 mmol) was added, and asolution of 3-(hydroxymethyl)phenylboronic acid (3.34 g, 22 mmol) in ethanol (20 mL) wassubsequently added dropwise. The reaction mixture was stirred at 90 C for 12 hours. The reactionmixture was cooled to room temperature and filtered. The aqueous phase was extracted with AcOEt(100 mL x 3). The combined organic layer was washed with H2O (30 mL) and brine (20 mL), and thendried over anhydrous Na2SO4, filtered and evaporated in vacuo. The residue was purified by flashchromatography over silica gel (petroleum/EtOAc = 10:13:1) to give(3-(5-fluoropyrimidin-2-yl)phenyl)methanol 5 (68%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,62802-42-0, its application will become more common.

Reference:
Article; Zhang, Niu-niu; An, Bai-jiao; Zhou, Yan; Li, Xing-shu; Yan, Ming; Molecules; vol. 24; 6; (2019);,
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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. 42754-96-1, name is 4,6-Dichloro-1H-pyrazolo[3,4-d]pyrimidine, molecular formula is C5H2Cl2N4, 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. SDS of cas: 42754-96-1

4,6-Dichloro-1H-pyrazolo[3,4-d]pyrimidine 1a (120 mg, 0.63 mmol), 4-methoxybenzylamine 1b (87.1 mg, 0.63 mmol) and triethylamine (64.13 mg, 0.63 mmol) were dissolved in 2 mL of tetrahydrofuran, and the reaction solution was stirred at room temperature for 1 hour. The reaction was stopped, and the reaction solution was concentrated under reduced pressure. The residue was purified by silica gel column chromatography with elution system A to obtain the title compound 1c (140 mg, yield: 76.1%). MS m/z (ESI): 290.2 [M+1]

With the rapid development of chemical substances, we look forward to future research findings about 42754-96-1.

Reference:
Patent; Jiangsu Hengrui Medicine Co., Ltd.; Shanghai Hengrui Pharmaceutical Co., Ltd.; ZHANG, Guobao; SHU, Chunfeng; HU, Qiyue; HE, Feng; TAO, Weikang; (59 pag.)EP3546457; (2019); A1;,
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Reference of 89466-39-7, 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.89466-39-7, name is 4-Chloro-6-methoxy-2-methylpyrimidine, molecular formula is C6H7ClN2O, molecular weight is 158.59, as common compound, the synthetic route is as follows.

General procedure: To a degassed solution of4,6-dichloropyrimidine (200 mg, 1.0 equiv) and arylboronic acid (1.0 equiv) in iPrOH (4 mL) in a 20 mLmicrowave vial was added an aqueous solution of 2M Na2CO3 (2.5 equiv) and Pd(PPh3)4 (5.0 mol%)under an argon atmosphere and the resulting heterogeneous solution was further degassed for 10 min. Thevial was sealed and placed in an oil bath at 83 oC and the reaction mixture was refluxed for 18 h, cooled,diluted with H2O (20 mL) and the whole was extracted with EtOAc (3 X 30 mL). The combined organicextract was washed with brine, dried (Na2SO4), and evaporated under reduced pressure give an oil whichwas purified by gradient column chromatography on silica gel using EtOAc/hexanes as eluent to affordcompounds 9a-j.

The chemical industry reduces the impact on the environment during synthesis 89466-39-7, I believe this compound will play a more active role in future production and life.

Reference:
Article; Gupta, Sahaj; Melanson, Jennifer A.; Selim Hossain; Vaillancourt, Louis; Tanoury, Gerald J.; Nugent, William A.; Snieckus, Victor; Heterocycles; vol. 96; 9; (2018); p. 1549 – 1569;,
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Reference of 40230-24-8, 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 40230-24-8, name is 4,6-Diphenylpyrimidin-2-amine. This compound has unique chemical properties. The synthetic route is as follows.

98.9 g (0.4 mol) of 2-amino-4,6-diphenyl-1,3-pyrimidine (compound 1) are introduced into a solution consisting of 1.5 l of water and 1 l of concentrated sulfuric acid. A solution of 75.0 g (1.088 mol) of sodium nitrite in 500 ml of water is added dropwise below the surface of the yellow suspension over the course of 25 hours. After 20 hours at 20-25 C. the yellow suspension is poured into 15 l of water and is rendered alkaline using 2.25 l of 25% aq. ammonia. The product precipitates as a beige solid. It is filtered off, washed with water and dried in a vacuum oven. 88.3 g (=88.9% yield) of beige crystals are obtained of the formula [C00057] [00399] with a melting point of 234-236 C.

According to the analysis of related databases, 40230-24-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Ciba Specialty Chemicals Corporation; US6706215; (2004); B1;,
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Synthetic Route of 35265-82-8, Adding some certain compound to certain chemical reactions, such as: 35265-82-8, name is 2,4-Dichloro-6-methylthieno[3,2-d]pyrimidine,molecular formula is C7H4Cl2N2S, 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 35265-82-8.

2,4-Dichloro-6-methylthieno[3,2-d]pyrimidine (820 mg, 3.76 mmol) was dissolved in tetrahydrofuran (20 mL) and deuterium methanol (2 mL), and the reaction solution was cooled to 0 C., deuterium sodium borohydride (632 mg, 15.04 mmol) was added in portions. The reaction solution was warmed to room temperature and stirred for another 16 hours. The reaction solution was diluted with saturated ammonium chloride solution (40 mL) and the aqueous phase was extracted with ethyl acetate (80 mL×2). The organic layers were combined, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated to give compound 51-e (660 mg, yield 93.4%) which was used for the next step without further purification. LC-MS (ESI): m/z=189.1[M+H]+.

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. 35265-82-8, 2,4-Dichloro-6-methylthieno[3,2-d]pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GUANGZHOU MAXINOVEL PHARMACEUTICALS CO., LTD.; XU, Zusheng; ZHANG, Nong; WANG, Tinghan; SUN, Qingrui; WANG, Yuguang; (90 pag.)US2018/208604; (2018); A1;,
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Electric Literature of 157335-97-2, 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.157335-97-2, name is 5-Bromo-4,6-dimethylpyrimidine, molecular formula is C6H7BrN2, molecular weight is 187.0372, as common compound, the synthetic route is as follows.

5-{[tert-Butyl(d imethyl)silyl]oxy}-2-(4 ,4,5,5-tetramethyl-1 ,3 ,2-dioxaborolan-2- yl)benzonitrile (C15) (4.05 g, 11.3 mmol) was combined with 5-bromo-4,6-dimethylpyrimidine hydrobromide (7.16 g, 26.7 mmol) and potassium phosphate (7.03 g, 33.1 mmol) in 2-methyltetrahydrofuran (20.2 mL) and water (16.2 mL). [2-(Azanidyl-KN)biphenyl-2-yl- K02](chloro)[dicyclohexyl(2,6-dimethoxybiphenyl-2-yl)-A5-phosphanyl]palladium (prepared from biphenyl-2-am me and dicyclohexyl(2,6-dimethoxybiphenyl-2-yl)phosphane (S-Phos) according to the procedure of S. L. Buchwald et al., J. Am. Chem. Soc. 2010, 132, 14073-14075) (0.20 g, 0.28 mmol) was added, and the reaction mixture was heated to reflux for 18 hours. It was thencooled to room temperature, and the organic layer was extracted with aqueous hydrochloric acid (2 N, 2 x 20 mL). The combined extracts were adjusted to a pH of roughly 6 – 7 with 2 M aqueous sodium hydroxide solution, and then extracted with ethyl acetate. These combined organic layers were dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting solids were triturated with hot heptane to afford the product as a tan solid. Yield: 1.86g, 8.26 mmol, 73%. H NMR (400 MHz, DMSO-d6) oe 10.48 (s, 1H), 8.94 (s, 1H), 7.36 (d, J=8.4 Hz, 1H), 7.31 (d, J=2.5 Hz, 1H), 7.23 (dd, J=8.5, 2.6 Hz, 1H), 2.18 (s, 6H).

Statistics shows that 157335-97-2 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-4,6-dimethylpyrimidine.

Reference:
Patent; PFIZER INC.; COE, Jotham, Wadsworth; ALLEN, John, Arthur; DAVOREN, Jennifer, Elizabeth; DOUNAY, Amy, Beth; EFREMOV, Ivan, Viktorovich; GRAY, David, Lawrence, Firman; GUILMETTE, Edward, Raymond; HARRIS, Anthony, Richard; HELAL, Christopher, John; HENDERSON, Jaclyn, Louise; MENTE, Scot, Richard; NASON, Deane, Milford, II; O’NEIL, Steven, Victor; SUBRAMANYAM, Chakrapani; XU, Wenjian; WO2014/72881; (2014); A1;,
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Application of 14080-50-3 ,Some common heterocyclic compound, 14080-50-3, molecular formula is C6H4N2OS, 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.

2nd step: 250 ml single-port bottle adding CP0763A 45g, phosphorus oxychloride 75 ml and N, N – dimethyl aniline 7.5 ml, heating reflux 2 hours for inspection, raw material of reaction. After the steaming and remove most of the phosphorus oxychloride, adding ice water quenching. Then the pH is adjusted with ammonia water 6 – 7, filtering, the filter cake is washed for three times. Solid dissolves clear EA adding activated carbon to decolorize. Drying reciprocation product job (CP0763 B) 34g. Yield: 68%;

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,14080-50-3, its application will become more common.

Reference:
Patent; Yang, Wei; Niu, Yuqiang; (14 pag.)CN104725398; (2017); B;,
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Synthetic Route of 60025-09-4 ,Some common heterocyclic compound, 60025-09-4, molecular formula is C5H3ClN4, 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.

S)-2-(1 -Aminoethyl)-5-((2-hydroxyphenyl)thio)-3-phenylpyrrolo[2,1 -f|[1 ,2,4]triazin- 4(3H)-one (183 mg, 0.36 mmol) was treated with 4-amino-6-chloropyrimidine-5- carbonitrile (84 mg, 0.54 mmol), and Lambda/,/V-diisopropylethylamine (380 muIota, 2.18 mmol) in ie f-butanol according to the method described in Example 17. The crude was purified by reverse phase using SP1Purification System to give 69 mg (38% yield) of the title compound as a white solid. Purity 100%.LRMS (m/z): 497 (M+1 )+1H NMR (400 MHz, DMSO-d6) delta 9.84 (s, 1 H), 7.78 (s, 1 H), 7.66 (t, J = 4.8 Hz, 2H), 7.49 (d, J = 8.0 Hz, 1 H), 7.46 – 7.38 (m, 1 H), 7.37 – 7.26 (m, 3H), 7.20 (s, 2H), 7.15 – 7.03 (m, 2H), 6.88 (dd, J = 8.0, 1.0 Hz, 1 H), 6.80 – 6.71 (m, 1 H), 6.25 (d, J = 2.8 Hz, 1 H), 4.88 (p, J = 6.6 Hz, 1 H), 1 .36 (d, J = 6.6 Hz, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,60025-09-4, its application will become more common.

Reference:
Patent; ALMIRALL, S.A.; ERRA SOLA, Montserrat; CARRASCAL RIERA, Marta; TALTAVULL MOLL, Joan; CATURLA JAVALOYES, Juan Francisco; BERNAL ANCHUELA, Francisco Javier; PAGES SANTACANA, Lluis Miquel; MIR CEPEDA, Marta; CASALS COLL, Gaspar; HERNANDEZ OLASAGARRE, Maria Begona; WO2014/60432; (2014); A1;,
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