Day: June 21, 2021

Adding a certain compound to certain chemical reactions, such as: 2380-63-4, 1H-Pyrazolo[3,4-d]pyrimidin-4-amine, 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, Computed Properties of C5H5N5, blongs to pyrimidines compound. Computed Properties of C5H5N5

1H-Pyrazolo[3,4-d]pyrimidin-4-amine (4, 0.10 g, 0.74 mmol) and N-iodosuccinimide (0.25 g, 1.1 mmol) in DMF (2 ml) were heated in a microwave at 90 C for 10 min. The resulting precipitate was filtered and washed with water to afford 5 as a brown solid in 92% yield (0.17 g, 0.65 mmol). 1H NMR (200 MHz, DMSO-d6): delta 13.82 (s, 1H), 8.18 (s, 1 H), 7.10 (b, 2 H); 13C NMR (50 MHz, DMSO-d6): delta 157.6, 156.0, 155.0, 102.5, 89.8; HRMS (CI) calcd for C5H5IN5 (M) 261.9511, found 261.9510.

The synthetic route of 2380-63-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Todorovic, Nick; Awuah, Emelia; Shakya, Tushar; Wright, Gerard D.; Capretta, Alfredo; Tetrahedron Letters; vol. 52; 44; (2011); p. 5761 – 5763;,
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. 60561-50-4, name is Methyl 2-(2-Pyrimidyl)acetate, the common compound, a new synthetic route is introduced below. SDS of cas: 60561-50-4

Step A: Methyl pyrrolo[1,2-a]pyrimidine-8-carboxylate (0122) To a solution of 6.2 g of methyl 2-pyrimidin-2-ylacetate (40.75 mmol) in 250 mL of acetone there are successively added 14.04 g (167 mmol) of NaHCO3 in the form of a powder, 13.2 mL (203.75 mmol) of chloroacetaldehyde and then 3.54 g (40.75 mmol) of lithium bromide. The batch is heated at 60 C. for 24 hours. The reaction mixture is then concentrated to dryness, taken up in ethyl acetate, washed with water, dried over MgSO4, filtered and then concentrated to dryness. The solid thereby obtained is then purified by chromatography over silica gel (AcOEt). The expected product is obtained in the form of an oil. (0123) Mass spectrum: (0124) Empirical formula: C8H8N2O2 (0125) LC/MS: m/z=[M+H]+=177

The synthetic route of 60561-50-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LES LABORATOIRES SERVIER; VERNALS (R&D) LIMITED; Le Tiran, Arnaud; Le Diguarher, Thierry; STARCK, Jerome-Benoit; Henlin, Jean-Michel; De Nanteuil, Guillaume; GENESTE, Olivier; Davidson, James Edward Paul; Murray, James Brooke; Chen, I-Jen; (36 pag.)US2016/176848; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 57054-92-9, 5-Bromo-2-chloro-4-methoxypyrimidine, 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 57054-92-9, blongs to pyrimidines compound. Product Details of 57054-92-9

To a mixture of (1S,2R)-2-(4-amino-3-cyclopropyl-pyrazol-1-yl)cyclopropanecarbonitrile (0.1 g, 531.27 mumol) and 5-bromo-2-chloro-4-methoxy-pyrimidine (119 mg, 531.27 mumol) in 1,4-dioxane (2 mL) was added p-TsOH.H2O (30 mg, 159.38 mumol) at 20 C. under N2. The mixture was stirred at 85 C. for 4 h. The mixture was poured into aq. NaHCO3 (5 mL) and extracted with EtOAc (3*5 mL). The combined organic phase was washed with brine (10 mL), dried with anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (PE:EtOAc=100:1 to 1:1) and separated by SFC to give (1S,2R)-2-[4-[(5-bromo-4-methoxy-pyrimidin-2-yl)amino]-3-cyclopropyl-pyrazol-1-yl]cyclopropanecarbonitrile and (1R,25)-2-[4-[(5-bromo-4-methoxy-pyrimidin-2-yl)amino]-3-cyclopropyl-pyrazol-1-yl]cyclopropanecarbonitriles

At the same time, in my other blogs, there are other synthetic methods of this type of compound,57054-92-9, 5-Bromo-2-chloro-4-methoxypyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Denali Therapeutics Inc.; Estrada, Anthony A.; Feng, Jianwen A.; Lyssikatos, Joseph P.; Sweeney, Zachary K.; de Vicente Fidalgo, Javier; (79 pag.)US2017/362206; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 3680-69-1, 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 3680-69-1 as follows.

To a suspension of 4-Chloro-7H-pyrrolo [2,3-d] pyrimidine (2.5g, 16 mmol) in CDC13 (65 mL) was added NBS (2.9g, 16 mmol) and the reaction mixture stirred and heated at reflux for 2.5 hours. The mixture was cooled to room temperature, the solids isolated by vacuum filtration, rinsed with cold CHC13 and air dried to give 5-Bromo-4-chloro-7H- pyrrolo [2, 3-d] pyrimidine (3. 0g, 79%. ) LCMS (APCI+) m/z 232 and 234 [M+H] + ; Rt: 2.32 min. 1H NMR (DMSO-d6,400 MHz) 6 12. 98 (1H, br. s), 8.63 (1H, s), 7.96 (1H, s. )

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3680-69-1, its application will become more common.

Reference:
Patent; ARRAY BIOPHARMA INC.; WO2005/51304; (2005); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 10070-92-5, 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.10070-92-5, name is Pyrimidine-5-carbaldehyde, molecular formula is C5H4N2O, molecular weight is 108.0981, as common compound, the synthetic route is as follows.

To a 1L 3-neck round bottomed flask equipped with an overhead stirrer, a thermocouple, a Dean-Stark trap (about 25 mL total volume), and a condenser with a nitrogen inlet was added 400.0 g of a 2.1 weight % solution of pyrimidine-5-carboxaldehyde in dichloromethane (8.4 g, 77.7 mmole contained pyrimidine-5-carboxaldehyde) and 7.39 g of 99.0 weight % 2-aminopyridine (77.7 mmole). The reaction mixture was heated to reflux under a nitrogen blanket and 349 g of dichloromethane were removed via the Dean-Stark trap at 39-48 C and atmospheric pressure. Toluene (126 mL) was added to the reaction mixture at about 48 C, followed by 31 mg of 98.5 weight % /?ara-toluenesulfonic acid monohydrate (0.16 mmol). The resulting reaction mixture was heated to reflux and distillate removed via the Dean-Stark trap until the temperature of the reaction mixture reached 110 C, at which point an additional 40 g of distillate had been removed. 50 mL of toluene was added to the reactor and the reaction mixture was refluxed at 112-1 14 C under atmospheric pressure for about 3.75 hours with removal of water via the Dean-Stark trap. HPLC analysis of the reaction mixture indicated 94.1 area % N-(5-pyrimidinylmethylene)-2-pyridinamine.

The chemical industry reduces the impact on the environment during synthesis 10070-92-5, I believe this compound will play a more active role in future production and life.

Reference:
Patent; E I DU PONT DE NEMOURS AND COMPANY; DUMAS, Donald J.; TRAN, Loc Thanh; (24 pag.)WO2017/189339; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 2927-71-1, Adding some certain compound to certain chemical reactions, such as: 2927-71-1, name is 2,4-Dichloro-5-fluoropyrimidine,molecular formula is C4HCl2FN2, 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 2927-71-1.

To a solution of 1.0M methylmagnesium bromide in tetrahydrofuran (270 ml) at 0C under nitrogen was added 2,4-dichloro-5-fluoropyrimidine (30 g) in 1,2- dimethoxyethane (90 ml) dropwise maintaining the temperature below 15C. The resulting solution was stirred at ~15C for one hour then cooled to 0C. A solution of triethylamine (25 ml) in dry tetrahydrofuran (40 ml) was added maintaining the temperature at ~5C, followed by a solution of iodine (45.6 g) in dry tetrahydrofuran (140 ml) maintaining the temperature below 15C. The reaction was quenched with water (400 ml) maintaining the temperature below 25C and treated with 5N aqueous hydrochloric acid solution (30 ml). The mixture was extracted with diethyl ether (2 x 500 ml) and the combined organic layer was washed with 2% w/w aqueous sodium metabisulfite (400 ml) and water (400 ml) then dried (MgS04) and evaporated. The residue was purified by silica gel column chromatography (gradient from 0 to 5% ethyl acetate / hexane) to afford the title compound (16.8 g) as an orange oil which was used in the next step without further purification. 1H-NMR (400 MHz, CDC13) delta (ppm): 2.57 (d, J=2.81 Hz, 3 H)

According to the analysis of related databases, 2927-71-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; EISAI R&D MANAGEMENT CO., LTD.; HALL, Adrian; FARTHING, Christopher Neil; EATHERTON, Andrew John; WO2014/13076; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 330785-84-7, 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.330785-84-7, name is (S)-4-((3-Chloro-4-methoxybenzyl)amino)-2-(2-(hydroxymethyl)pyrrolidin-1-yl)pyrimidine-5-carboxylic acid, molecular formula is C18H21ClN4O4, molecular weight is 392.84, as common compound, the synthetic route is as follows.

In DMF (20 mL) was dissolved (s)-4-((3-chloro-4-methoxybenzyl)amino)-2-(2 -(hydroxymethyl)tetrahydropyrrole-1-yl)-5-pyrimidine carboxylic acid (3.9 g, 10 mmol). The solution was cooled in an ice bath. HATU (5.67 g, 15 mmol) and DIPEA (1.93 g, 15 mmol) were added. After 20 min, trans-4-aminocyclohexanol (1.39 g, 12 mmol) was added in batches. The reaction was conducted overnight. LC-MS was used to monitor the reaction. Ethyl acetate (50 mL) and water (50 mL) were added. The separate aqueous phase was washed with ethyl acetate twice. The organic phase was combined, dried, concentrated and purified by silica gel column chromatography (VDCM:VMeOH = 15:1) to give the product (1.5 g, 31 % yield). Molecular formula: C24H32ClN5O4 Molecular weight: 489.21 LC-MS(M/e): 490.11 (M+H+) 1H-NMR (400 MHz, CDCl3): delta 9.63 (1H, s), 8.15 (1H, s), 7.35(1H, s), 7.19 (1H, d), 7.1 (1H, d), 6.26 (1H, s), 4.58 (2H, d), 4.05-4.13 (1H, m), 3.79-3.90 (6H, m), 3.56-3.69 (3H, m), 2.22-2.27 (2 H, m), 1.72-2.17 (8H, m), 1.26-1.45 (4H, m).

Statistics shows that 330785-84-7 is playing an increasingly important role. we look forward to future research findings about (S)-4-((3-Chloro-4-methoxybenzyl)amino)-2-(2-(hydroxymethyl)pyrrolidin-1-yl)pyrimidine-5-carboxylic acid.

Reference:
Patent; Xuanzhu Pharma Co., Ltd.; WU, Frank; WANG, Aichen; EP2886540; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
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. 1013916-37-4, name is 2-Chloro-8-cyclopentyl-5-methylpyrido[2,3-d]pyrimidin-7(8H)-one, molecular formula is C13H14ClN3O, 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. COA of Formula: C13H14ClN3O

Add to dry and clean 2000ml reaction bottle8-cyclopentyl-5-methyl-2-chloro-8H-pyrido[2,3-d]pyrimidinePyridin-7-one (Formula 7) 60g, dissolved in 600g of dichloromethane,Add 90 g of sodium acetate and add 6.0 g of acetic acid.Add 100.0 g of bromine at 0-20 ,After the addition is completed,Stirring reaction for 5 hours,After TLC monitors the reaction of the raw materials,An aqueous solution of 15% sodium hydrogen sulfite in an amount of 800 g was added dropwise.Until the reddish brown bromine was completely destroyed,Stir, dispense,The organic layer is washed twice with water.Wash once again with saturated brine.Distilled under reduced pressure until no flow,Beating with ethanol-water (300g 300g) for 2h,Filtering,The target compound was obtained 65.7g,The yield is 84.28%.The purity of 99.5% of the compound of formula 9 is 0.07%.The compound of formula 10 is present in an amount of 0.01%.

With the rapid development of chemical substances, we look forward to future research findings about 1013916-37-4.

Reference:
Patent; Guang’an Kaite Pharmaceutical Co., Ltd.; Zhang Yaochun; Zhou Fuwei; Liu Xinjun; Zuo Xiaoyong; Zhou Xudong; (11 pag.)CN109320511; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
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. 139756-21-1, name is 5-(2-Ethoxyphenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one. A new synthetic method of this compound is introduced below., COA of Formula: C17H20N4O2

EXAMPLE 21 5-(5-Bromo-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]-pyrimidin-7-one Bromine (0.93 g, 0.0058 mol) was added dropwise to a stirred solution of 5-(2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]-pyrimidin-7-one (Preparation 7, 1.1 g, 0.00352 mol) in glacial acetic acid (20 ml). The mixture was stirred at 100 C. for 6.5 hours and the solvent was then removed by evaporation under vacuum. The residue was dissolved in a 9:1 mixture of methanol in dichloromethane (50 ml), and the solution washed with saturated aqueous sodium bicarbonate solution (50 ml), water (50 ml) and saturated brine (50 ml), then dried (MgSO4) and evaported under vacuum. The residue was chromatographed in silica gel (15 g) eluding with a mixture of methanol and dichloromethane (1:99) to give, after crystallisation from acetonitrile, the title compound (0.62 g, 45%), m.p. 157-159 C. Found C,52,41; H,5.25; N,14.01. C17 H19 BrN4 O2 requires C,52.18; H,4.89; N,14.32%.

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, 139756-21-1, 5-(2-Ethoxyphenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one.

Reference:
Patent; Pfizer Inc.; US5272147; (1993); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 1202759-91-8, 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. 1202759-91-8, name is N4-(3-Aminophenyl)-5-fluoro-N2-(4-(2-methoxyethoxy)phenyl)pyrimidine-2,4-diamine. A new synthetic method of this compound is introduced below.

Into a 25 ml, three neck flask under nitrogen atmosphere, a solution of N4-(3-aminophenyl)-5-fluoro-N2-(4-(2-methoxyethoxy)phenyl)pyrimidine-2,4-diamine (0.15 g) in DMF (5 mL) was charged potassium 3-ethoxy-3-oxopropanoate (0.089 g), EDCI.HCl (0.117 g), HOBt (0.093 g) and TEA (0.164 g). The reaction mixture was stirred for 8 hr at room temperature. Completion of the reaction was monitored by TLC using hexane:ethyl acetate (5:5) as the mobile phase. After completion, the reaction mixture was poured into water. The product was extracted with ethyl acetate and the organic layer was washed with brine. The solvent was removed under reduced pressure at 40 C. The obtained solid was purified by triturating with diethyl ether (2×10 mL) to give 0.19 g of ethyl 3-((3-((5-fluoro-2-((4-(2-methoxyethoxy)phenyl)amino)pyrimidin-4-yl)amino)phenyl)amino)-3-oxopropanoate. 1H NMR: DMSO-d6 (400 MHz): 1.182-1.234 (q, 3H, J=6.8), 3.306 (s, 3H), 3.461 (s, 2H), 3.623-3.646 (t, 2H, J=4.8), 4.010-4.033 (t, 2H, J=4.4), 4.090-4.144 (t, 2H, J=7.2), 6.775-6.797 (d, 2H, J=8.8), 7.267-7.283 (d, 2H, J=6.4), 7.511-7.533 (d, 1H, J=8), 7.575-7.591 (d, 1H, J=6.4), 7.817 (s, 1H), 8.058-8.066 (d, 1H, J=3.2), 8.963 (s, 1H), 9.375 (s, 1H), 10.162 (s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1202759-91-8, its application will become more common.

Reference:
Patent; Celgene Avilomics Research, Inc.; Tester, Richland; Chaturvedi, Prasoon; Zhu, Zhendong; Surapaneni, Sekhar S.; Beebe, Lisa; US2014/179720; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia