Month: August 2021

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.100644-67-5, name is 4-Methoxy-1H-pyrazolo[3,4-d]pyrimidin-6-amine, molecular formula is C6H7N5O, molecular weight is 165.15, as common compound, the synthetic route is as follows.category: pyrimidines

6-Amino-4-methoxy-1H-pyrazolo[3,4-d]pyrimidine (purine base A; 8.0 g, 48.4 mmol, 1.0 eq) wassuspended in 200 mL dry acetonitrile and 1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose (ribose I) (36.6g, 72.6 mmol, 1.5 eq) was added. The reaction mixture was heated to reflux at 95 C, and the freshlydistilled BF3OEt2 (12.2 mL, 96.8 mmol, 2.0 eq) was then added with stirring. The reaction mixturebecame clear immediately and then slowly became dark. The mixture was stirred at this temperaturefor 15 min. Upon the completion of the reaction as monitored by TLC, the reaction mixture was cooledto room temperature and concentrated under reduced pressure. The resulting residue was purified bycolumn chromatography to afford 25.0 g N8-product 25 as a white solid in 83.3% yield with an HPLCpurity of 96.8%. Rf = 0.6 (dichloromethane-methanol = 30:1). UV-vis (MeOH) lmax: 225 nm; ESI-MSm/z: 610.6 [M + H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,100644-67-5, 4-Methoxy-1H-pyrazolo[3,4-d]pyrimidin-6-amine, and friends who are interested can also refer to it.

Reference:
Article; Ren, Hang; An, Haoyun; Tao, Jingchao; Molecules; vol. 24; 5; (2019);,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 1193-21-1 ,Some common heterocyclic compound, 1193-21-1, molecular formula is C4H2Cl2N2, 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.

PREPARATION D 4-Chloro-6-isopropoxy-pyrimidine STR48 A solution of sodium isopropoxide (prepared from 0.77 g sodium) in isopropanol (230 ml) was added dropwise over 8 hours to a stirred solution of 4,6-dichloropyrimidine (5.0 g) in isopropanol (60 ml) at room temperature. The solvent was evaporated in vacuo, the residue taken up in water and extracted three times with diethylether (3*70 ml). The combined ether extracts were dried (Na2 SO4) and evaporated in vacuo to give 4-chloro-6-isopropoxy pyrimidine (4.4 g) as an oil, characterized spectroscopically, and used directly.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1193-21-1, its application will become more common.

Reference:
Patent; Pfizer Inc.; US4435401; (1984); A;,
Pyrimidine | C4H4N2 – PubChem,
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. 26032-72-4, name is 2,4-Dichloro-6-phenylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Formula: C10H6Cl2N2

General Method 2 Step 2A.2. To 1 mmol of 2,4-dichloro-6-phenylpyrimidine (X) and 4-chloroaniline in 4 mL of dry THF was added 1 mmol (0.5 mL, 2M in THF/heptane/ethylbenzene) of lithium diisopropylamide. The reaction was followed by TLC (30% ethyl acetate/hexane). The reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate and the organic layers were dried over magnesium sulfate and concentrated under reduced pressure. The mixture was purified by chromatography on silica gel with elution by 30% ethyl acetate/hexanes to afford 70 mg of 2-chloro-N-(4-chlorophenyl)-6-phenylpyrimidin-4-amine (XII) as an amorphous solid. ESI/MS 315.883, 317.915 (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, 26032-72-4, 2,4-Dichloro-6-phenylpyrimidine.

Reference:
Patent; Vestaron Corporation; US2012/22066; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 3764-01-0 ,Some common heterocyclic compound, 3764-01-0, molecular formula is C4HCl3N2, 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.

In a 500 mL three-necked flask under argon atmosphere, 2,4,6-trichloropyrimidine (5 g, 27.3 mmol), phenylboronic acid (6.7 g, 54.9 mmol), tetrakistriphenylphosphine palladium (1.26 g, 1.09 mmol ), Dimethoxyethane (DME, 100 mL) and a 2M sodium carbonate aqueous solution (82 mL, 164 mmol) were added, and the mixture was reacted for 8 hours while heating and refluxing. After the reaction solution was cooled to room temperature, the aqueous layer was separated and the organic layer was dried over magnesium sulfate. The insoluble material was removed by filtration, and the organic solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain intermediate (a) (5.6 g, yield 76.9%).

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. 3764-01-0, 2,4,6-Trichloropyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Idemitsu Kosan Corporation; Nishimura, Kazuki; Ito, Mitsunori; Inoue, Tetsuya; (48 pag.)KR2015/92145; (2015); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 698-29-3, 4-Amino-2-methylpyrimidine-5-carbonitrile, 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, category: pyrimidines, blongs to pyrimidines compound. category: pyrimidines

Method A 6-(2,6-Dichlorophenyl)-2-methylpyrido[2,3,-d]-pyrimidin-7-amine A mixture of 76.5 g of 4-amino-2-methylpyrimidine-5-carbonitrile, 380 ml of 97% formic acid, 380 ml of water, and 8 g of Raney nickel catalyst is treated in a Parr pressure apparatus with hydrogen gas at an initial pressure of 51 psi at room temperature for 2.75 hours. The catalyst is removed by filtration and the filtrate is treated with 47.5 ml of concentrated hydrochloric acid and evaporated at reduced pressure. The residue is dissolved in hot water, treated with charcoal and filtered. Neutralization of the filtrate with concentrated ammonium hydroxide precipitates the product which is then collected by filtration and washed with water. Recrystallization from ethanol gives 37.9 g of 4-amino-2-methylpyrimidine-5-carboxaldehyde, mp 191-192.5 C.

The synthetic route of 698-29-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Warner-Lambert Company; US4271164; (1981); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 18740-39-1, 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 18740-39-1, name is 2,4-Dichlorothieno[2,3-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Pd(PPh3)2Cl2 (23 mg, 0.03 mmol), 4-trifluoromethoxyphenylboronic acid (73 mg, 0.35 mmol), compound 15 (100 mg, 0.32 mmol) and TEA (91 mg, 0.90 mmol) were added to a solution of DMF (5 mL) and H2O (0.5 mL). The mixture was stirred at 80 oC for 4 h. Water (10 mL) and EtOAc (30 mL) were added to the reaction. The layers were separated. The aqueous layer was extracted using EtOAc (10 mL). The combined organic extracts were dried over anhydrous Na2SO4. The solvent was removed under reduced pressure, and the resulting residue was purified via silica gel column chromatography using petroleum ether/EtOAc (5/1) to give 16 (67 mg, 48 percent) as a yellow solid.

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 18740-39-1, 2,4-Dichlorothieno[2,3-d]pyrimidine.

Reference:
Article; Zhang, Liandi; Xin, Minhang; Shen, Han; Wen, Jun; Tang, Feng; Tu, Chongxing; Zhao, Xinge; Wei, Ping; Bioorganic and Medicinal Chemistry Letters; vol. 24; 15; (2014); p. 3486 – 3492;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 5399-92-8, 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. 5399-92-8, name is 4-Chloro-1H-pyrazolo[3,4-d]pyrimidine, molecular formula is C5H3ClN4, 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.

To a stirred solution of 4-chloro-1H-pyrazolo[3,4-d]pyrimidine (2.5 g, 16.23 mmol, 1 equiv) in DCM (30 mL) was added NBS (3.4 g, 19.48 mmol, 1.2 equiv) at 000. The reaction mixture was warmed to room temperature and stirred for 0/N. The reaction mixture was quenched with water and extracted with ethyl acetate. The organic layer was dried over sodium sulphate evaporated to obtain crude which was purified over silica gel flash column chromatography. The compound eluted out in 15% ethyl acetate in n-hexane to afford 3-bromo-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one (1.3 g, crude) as pale yellow solid. 1H NMR (400 MHz, DMSO-d6) O ppm – 8.02 (s, 1H), 12.18 (s, 1H), 14.00 (br.s, 1H)

According to the analysis of related databases, 5399-92-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; AXTEN, Jeffrey Michael; FAUCHER, Nicolas Eric; DAUGAN, Alain Claude-Marie; (110 pag.)WO2017/46738; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 374930-88-8, 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 374930-88-8, name is tert-Butyl 4-(5-bromopyrimidin-2-yl)piperazine-1-carboxylate. This compound has unique chemical properties. The synthetic route is as follows.

Step 1: Synthesis of tert-butyl 4-(5-(cyclopropylethynyl)pyrimidin-2-yl)piperazine-1-carboxylate In a sealed tube, the mixture of tert-butyl 4-(5-bromopyrimidin-2-yl)piperazine-1-carboxylate (1.0 g, 2.9 mmol), ethynylcyclopropane (482 mg, 7.3 mmol), tetrakis(triphenyl-phosphine)palladium (335 mg, 0.29 mmol) and copper(I) iodide (28 mg, 0.15 mmol) in diethylamine (10 mL) and dimethyl sulfoxide (10 mL) was stirred at 100 C. for 3 hours under nitrogen atmosphere. The mixture was then diluted with ethyl acetate (100 mL) and washed with water and brine. The organic phase was dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography eluting with petroleum ether:ethyl acetate=15:1 to afford tert-butyl 4-(5-(cyclopropylethynyl)pyrimidin-2-yl)piperazine-1-carboxylate (930 mg, 98%) as a yellow solid. MS (ES+) C18H24N4O2 requires: 328, found: 329 [M+H]+.

According to the analysis of related databases, 374930-88-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BLUEPRINT MEDICINES CORPORATION; Hodous, Brian L.; Kim, Joseph L.; Miduturu, Chandrasekhar V.; Wilson, Douglas; Zhang, Yulian; US2015/111857; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
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. 139756-21-1, name is 5-(2-Ethoxyphenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 5-(2-Ethoxyphenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one

PREPARATION 17 5-(2-Ethoxy-5-nitrophenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]-pyrimidin-7-one Concentrated nitric acid (0.5 ml) 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 (2.0 g, 0.0064 mol) in concentrated sulphuric acid (10 ml) at 0 C., an the resulting orange solution was stirred at room temperature for 18 hours. The reaction solution was then added dropwise to stirred ice and water (200 g) and the solid precipitate collected by filtration. This solid was then dissolved in dichloromethane (50 ml) and the solution washed successively with brine (2*30 ml) and water (30 ml), dried (Na2 SO4) and evaporated under vacuum to give a yellow solid. Crystallisation from acetronitrile gave the title compound as yellow needles (1.40 g, 61%), m.p. 214-216 C. Found: C,57.36; H,5.21; N,19.49. C17 H19 N5 O4 requires C,57.13; H,5.36; N,19.60%.

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

Related Products of 16019-31-1, 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 16019-31-1 as follows.

A solution of compound 4 (100 g, 0.53 mol) in MeOH (400 ml) and CH2Cl2 (150 ml) was cooled to -40C, and ozone was bubbled through the mixture for 2 h. Then the reaction mixture was purged with nitrogen for 20 min to remove the excessive ozone. Thiocarbamide (40 g, 0.53 mol) was added to the mixture and stirred for 1 h until the starch-KI paper did not turn blue. The solvent was distilled off, the residue was extracted with CH2Cl2 (300 ml) and washed with water (2×100 ml). The organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure to give the residue that was triturated with petroleum ether (200 ml). Yield 76.8 g (76%), white solid, mp 88-90C (mp 89-91C19). 1H NMR spectrum (DMSO-d6), delta, ppm: 9.75 (1H, s, CHO); 8.89 (1H, s, H-2); 4.24 (2H, s, CH2).13C NMR spectrum (DMSO-d6), delta, ppm: 196.9; 161.8;157.0; 126.4; 44.5. Mass spectrum, m/z (Irel, %): 192[M(35Cl,37Cl)]+(12), 190 [M(35Cl)]+ (20), 162 (100).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,16019-31-1, its application will become more common.

Reference:
Article; Zhang, Yu-Liu; Xu, Cheng-Tao; Liu, Ting; Zhu, Yong; Luo, Yu; Chemistry of Heterocyclic Compounds; vol. 54; 6; (2018); p. 638 – 642; Khim. Geterotsikl. Soedin.; vol. 54; 6; (2018); p. 638 – 642,5;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia