Pyrimidines

Synthetic Route of 7461-50-9 ,Some common heterocyclic compound, 7461-50-9, 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.

Example 1 N-(4-((4-Aminopyrimidin-2-yloxy)methyl)benzyl)-2,2,2-trifluoroacetamide (1) 760 mg (3.25 mmol) 2,2,2-Trifluoro-N-(4-hydroxymethyl-benzyl)-acetamide is dissolved in 3 mL dry dimethylacetamide under argon atmosphere, and 273 mg (8.15 mmol) NaH is added over 5 min. 211 mg (1.63 mmol) 2-Chloropyrimidin-4-amine is then added and the solution stirred at 90C over night. 1 mL Water is added carefully to quench all excess NaH, and the mixture poured into 50 ml of 0.5 N HCI. The crude product is extracted with ethyl acetate, the combined organic phases washed with brine and dried over MgSO4. After evaporation of the solvent, the product is purified by flash column chromatography (gradient ethyl acetate:cyclohexane from 1:1 to 3:1). Yield: 350 mg (52%). ESI-MS m/z 327 [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. 7461-50-9, 2-Chloropyrimidin-4-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; EPFL Ecole Polytechnique Federale de Lausanne; EP1882688; (2008); A1;,
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Electric Literature of 75833-38-4, 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.75833-38-4, name is 2-Chloropyrimidine-4-carbonitrile, molecular formula is C5H2ClN3, molecular weight is 139.54, as common compound, the synthetic route is as follows.

A solution of 2-chloropyrimidine-4-carbonitrile (163 mg, 1.17 mmol), 2-amino-1-(piperidin-1-yl)ethanone hydrochloride (240 mg, 1.34 mmol) and DIPEA (0.510 mL, 2.92 mmol) in acetonitrile (2 mL) was stirred at 100 C for 16 hr. The reaction mixture was partitioned between ethyl acetate (20 mL) and water (20 mL), and the organic layer was washed with water (20 mL). The aqueous was back-extracted with ethyl acetate (2 x 10 mL) and the combined organic layers were dried through a hydrophobic frit and evaporated to dryness. The crude product was purified by silica chromatography (0-50 % (3:1 ethyl acetate:ethanol + 1 %triethylamine)/cyclohexane). Appropriate fractions were evaporated to dryness to afford 2-((2-oxo-2-(piperidin-1-yl)ethyl)amino)pyrimidine-4-carbonitrile (240 mg, 0.978 mmol, 84 % yield) as a yellow solid. LCMS (High pH, ES+): tR = 0.80 min, [M+H+ 246.2. 1H NMR (400 MHz, CDCl3) delta 1.52 – 1.76 (m, 6 H), 3.42 (t, J = 5.1 Hz, 2 H), 3.54 – 3.67 (m, 2 H), 4.16 (d, J = 4.0 Hz, 2 H), 6.67 (br. s., 1 H), 6.85 (d, J = 4.5 Hz, 1 H), 8.47 (d, J = 4.8 Hz, 1 H). 13C NMR (101 MHz, CDCl3) delta 24.4, 25.4, 26.2, 43.0, 43.2, 45.5, 113.5, 116.1, 141.3, 160.1, 161.6, 165.9. numax (neat): 3347, 2935, 2854, 1643, 1579, 1547, 1529, 1481, 1440, 1403, 1339, 1255, 1233, 1200, 1134, 1077, 1008, 855, 805, 734 cm-1. HRMS: (C12H16N5O) [M+H]+ requires 246.1349, found [M+H]+ 246.1342.

The chemical industry reduces the impact on the environment during synthesis 75833-38-4, I believe this compound will play a more active role in future production and life.

Reference:
Article; Law, Robert P.; Ukuser, Sabri; Tape, Daniel T.; Talbot, Eric P. A.; Synthesis; vol. 49; 16; (2017); p. 3775 – 3793;,
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Adding a certain compound to certain chemical reactions, such as: 211244-81-4, 2-(Methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one, 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, Recommanded Product: 2-(Methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one, blongs to pyrimidines compound. Recommanded Product: 2-(Methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one

Step 1: Synthesis of 6-bromo-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one (7)¡¤[00372] To a solution of 2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one (6, 1.00 g, 5.2 mmol) in anhydrous dimethylformamide (25 mL) was added A jromosuccinimide (0.99 g, 5.6 mmol) portionwise at room temperature, and the reaction mixture was stirred for 18 h. The mixture was concentrated, and the solid was triturated with hot water (1 x 20 mL), filtered, and washed with isopropanol to give title compound as a pale yellow solid (0.68 g, 2.5 mmol, 48%). ESMS m/z 272 (M+H)+; ? NMR (400 MHz, DMSO-Patent; AFRAXIS, INC.; CAMPBELL, David; DURON, Sergio, G.; VOLLRATH, Benedikt; WADE, Warren; WO2011/156786; (2011); A2;,
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Application of 1480-96-2, Adding some certain compound to certain chemical reactions, such as: 1480-96-2, name is 5-Fluoro-2-methoxypyrimidin-4(3H)-one,molecular formula is C5H5FN2O2, 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 1480-96-2.

500 g of methanol was placed in a constant-temperature reaction bath, and hydrogen chloride gas was introduced until the methanol increased weight to 543 g-556 g to stop aeration. The prepared methanol solution of hydrogen chloride was placed in a refrigerator for use.In a dry and clean 500 mL four-neck flask, 250 g of hydrochloric acid in methanol was added, and 50 g of 2-methoxy-5-fluorouracil was stirred. When the temperature was raised to 28 C., incubation was started. After 5 h, samples were taken for HPLC detection. At 0.07%, the reaction was completed, the temperature was lowered to 15C, and the resulting solid was suction filtered.The refined 5-fluorouracil is refined and the mother liquor is concentrated after suction filtrationShrink the recovered methanol for use. The resulting 5-fluorouracil dry weight was 35.4 g, with a purity of 99.82% and a yield of 78.3%.

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. 1480-96-2, 5-Fluoro-2-methoxypyrimidin-4(3H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Jinghua Pharmaceutical Group Nantong Co., Ltd.; Yuan Yongjun; Shen Xiaojuan; Li Shufen; Chen Xuelian; Wu Yuxiang; (4 pag.)CN107963994; (2018); A;,
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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. 23002-51-9, name is 6-Chloro-1H-pyrazolo[3,4-d]pyrimidine, the common compound, a new synthetic route is introduced below. category: pyrimidines

A mixture of 6-chloro-1H-pyrazolo[3,4-djpyrimidine (1.25 g, 8.09 mmol), pyridinium ptoluene sulfonate (203 mg, 0.81 mmol) and 3,4-dihydro-2h-pyran (1.36 g, 16.17 mmol) indichloromethane (25 mL) was heated at reflux for 6 h and concentrated under reduced pressure. Theresidue was purified by column chromatography (silica gel, 100-200 mesh, 0 to 40% ethyl acetate inpetroleum ether) to afford 6-chloro- 1 -tetrahydropyran-2-yl-pyrazolo [3 ,4-djpyrimidine (1.8 g, 93%)as a white solid. 1H NMR(400 MHz, CDCl3) d 9.10 – 8.99 (m, 1H), 8.26 – 8.14 (m, 1H), 6.13 – 5.98 (m, 1H), 4.21 – 4.09 (m, 1H), 3.91 – 3.76 (m, 1H), 2.67 – 2.48 (m, 1H), 2.59 – 2.48 (m, 1H), 2.21 – 2.09 (m, 1H), 2.00 – 1.91 (m, 1H), 1.86 – 1.75 (m, 2H), 1.70 – 1.60 (m, 1H).

The synthetic route of 23002-51-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GENENTECH, INC.; F. HOFFMANN-LA ROCHE AG; PATEL, Snahel; (77 pag.)WO2019/204537; (2019); A1;,
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Electric Literature of 186046-78-6, 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. 186046-78-6, name is 2-(4-(((Benzhydryloxy)carbonyl)amino)-2-oxopyrimidin-1(2H)-yl)acetic acid, molecular formula is C20H17N3O5, 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.

Example 50 N-{[4-N-(Benzhydryloxycarbonyl)-cytosin- 1 -yl]-acetyl}-N-[2-(2-nitro-benzenesulfonylamino)-ethyl]-glycine ethyl ester The title compound (2.45 g, 88%) was synthesised by the reaction of N-[2-(2-nitro-benzenesulfonylamino)-ethyl]-glycine ethyl ester (1.33 g, 4 mmol) and 2-[4-N-(benzhydryloxycarbonyl)-cytosin-1-yl]-acetic acid (1.51 g, 4 mmol) as per the procedure of example 46. 1H-NMR (500 MHz; DMSO-d6) delta 10.99 (s, 0.6H,), 10.98 (s, 0.4H), 8.30~7.80 (m, 5H), 7.50~7.25 (m, 10H), 6.94 (t, 1H), 6.79 (s, 1H), 4.79 (s, 1.2H), 4.61 (s, 0.8H), 4.33 (s, 0.8H), 4.15 (q, 0.8H), 4.05 (q, 1.2H), 4.01 (s, 1.2H),, 3.52 (t, 1.2H), 3.36 (t, 0.8H), 3.24 (q, 1.2H), 3.02 (q, 0.8H), 1.23 (t, 1.2H), 1.15 (t, 1.8H).

According to the analysis of related databases, 186046-78-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Kim, Sung Kee; Lee, Hyunil; Lim, Jong Chan; Choi, Hoon; Jeon, Jae Hoon; Ahn, Sang Youl; Lee, Sung Hee; US2003/195332; (2003); A1;,
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Electric Literature of 705263-10-1 , The common heterocyclic compound, 705263-10-1, name is 6-Bromopyrazolo[1,5-a]pyrimidine, molecular formula is C6H4BrN3, 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.

Example 1 6-Phenylethynyl-pyrazolo[1,5-a]pyrimidine Bis-(triphenylphosphine)-palladium(II) dichloride (27 mg, 0.04 mmol) was dissolved in 1 ml of THF. 6-Bromo-pyrazolo[1,5-a]pyrimidine (150 mg, 0.76 mmol) and phenylacetylene (130 mul, 1.21 mmol) were added at room temperature. Triethylamine (310 mul, 2.3 mmol), triphenylphosphine (6 mg, 0.023 mmol) and copper(I) iodide (4 mg, 0.023 mmol) were added and the mixture was stirred for 2 hours at 65 C. The reaction mixture was cooled and extracted with saturated NaHCO3 solution and two times with a small volume of dichloromethane. The crude product was purified by flash chromatography by directly loading the dichloromethane layers onto a silica gel column and eluting with heptane:ethyl acetate 100:0->50:50. The desired compound was obtained as a yellow solid (150 mg, 90% yield), MS: m/e=220.3 (M+H+).

The synthetic route of 705263-10-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Green, Luke; Guba, Wolfgang; Jaeschke, Georg; Jolidon, Synese; Lindermann, Lothar; Stadler, Heinz; Vieira, Eric; US2011/152257; (2011); A1;,
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Electric Literature of 54326-16-8 ,Some common heterocyclic compound, 54326-16-8, molecular formula is C4H3ClN2O, 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.

EXAMPLE 12 5-Chloro-1-(1-oxo-1-phenylprop-2-yl)pyrimidin-2-one A solution of 5-chloropyrimidin-2-one (394 mg) and alpha-bromopropiophenone (0.5 ml) in triethylamine (1 ml) and ethanol (20 ml) was stirred at ambient temperature for 2.75 hours. The solution was evaporated and the residue was triturated with water (50 ml) giving an oily solid. This was extracted with ethyl acetate (3*50 ml). The combined extracts were washed with brine (50 ml), dried (MgSO4) and evaporated to a gum. This was crystallized from acetone-petrol (b.p. 40-60) to give the title pyrimidinone (306 mg,); m.p. 125-127; lambdamaxEtOH 232 nm (epsilon 15400), 245 nm (epsilon 15480), 335 nm (epsilon 3970).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,54326-16-8, its application will become more common.

Reference:
Patent; Glaxo Group Limited; US4636509; (1987); A;,
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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. 1152475-50-7, name is 2-Chloro-7-iodo-5H-pyrrolo[3,2-d]pyrimidine. A new synthetic method of this compound is introduced below., Formula: C6H3ClIN3

To a stirred solution of 2-chloro-7-iodo-5H-pyrrolo[3,2-d]pyrimidine (110 mg, 0.39 mmol) in DCM (5 ml) was added tetrabutylammonium bromide (19 mg, 0.06 mmol), NaOH (1 ml, 2M) and MeI (47 mul, 0.47 mmol) were added and the mixture was stirred for 16 hours at room temperature. Water, DCM and EtOAc were added and the phases were separated. Concentration by evaporation followed by trituration using Et2O gave 110 mg (94%) of the title compound. LC/MS (20-100% CH3CN:0.05% HCOOH(aq) gradient over 5 min): 3.07 min. 294 M+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, 1152475-50-7, 2-Chloro-7-iodo-5H-pyrrolo[3,2-d]pyrimidine.

Reference:
Patent; PFIZER INC.; Schnute, Mark Edward; Wennerstal, Goeran Mattias; Blinn, James Robert; Kaila, Neelu; Kiefer, JR., James Richard; Mente, Scot Richard; Kurumbail, Ravi G.; Meyers, Marvin Jay; Thorarensen, Atli; Xing, Li; Zapf, Christoph Wolfgang; Zamaratski, Edouard; Flick, Andrew Christopher; Jones, Peter; (77 pag.)US2016/46597; (2016); A1;,
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Synthetic Route of 13036-50-5, Adding some certain compound to certain chemical reactions, such as: 13036-50-5, name is 2-Chloro-4-phenylpyrimidine,molecular formula is C10H7ClN2, 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 13036-50-5.

To the obtained 2-chloro-4-phenylpyrimidine was added concentrated hydrochloric acid (~ 10 N) and stirred well. The homogeneous mixture was refluxed for 1 hour. The reaction mixture was poured into 10% aqueous sodium carbonate solution. The white precipitate was filtered off and dried to give a white solid. TLC was observed at R f: 02 (chloroform: methanol (9.5: 0.5))

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. 13036-50-5, 2-Chloro-4-phenylpyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; The Industry & Academic Cooperation in Chungnam National University (IAC); Jung, Sang-Hun; Woo, Sun-Hee; Kim, Sang- Kyum; Jeon, Eun-Seok; Lee, Yu-Jung; Meunikam, Manoj; Jalani, Hiteshkumar; Sharma, Niti; (205 pag.)KR2016/108281; (2016); A;,
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