Day: August 5, 2021

Application of 89581-38-4 ,Some common heterocyclic compound, 89581-38-4, molecular formula is C6H5BrN2O2, 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.

Under nitrogen, compound 1 (275 mg, 1.48 mmol), methyl-5- bromopyrimidine-2-carboxylate (165 mg, 0.76 mmol), Ruphos (33 mg, 0.07 mmol), Pd2(dba)3 (17 mg, 0. 018mmol) and Cs2C03 (748 mg, 2.29 mmol) were combined in toluene (8 mL) and heated to 100 C overnight. The crude residue was purified by preparative TLC (silica gel, GF254 10-40u, 25*25cm) with petroleum ether/EtOAc (1 :1 ) to afford Compound 2 as a white solid (80mg, 40%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,89581-38-4, its application will become more common.

Reference:
Patent; REGENACY PHARMACEUTICALS, LLC; VAN DUZER, John H.; MAZITSCHEK, Ralph; BLUM, Charles; JARPE, Matthew B.; (53 pag.)WO2020/76951; (2020); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 74840-38-3, 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 74840-38-3 as follows.

A solution of 5-bromo-2-methylthio-pyrimidine-4-carboxylic acid ethyl ester (100 mg, 0.36 mmol ; prepared from 5-bromo-2-methylthio-pyrimidine-4-carboxylic acid according to Coll. Czech. Chem. Commun. 1980, 45(2), 539) in dichloromethane (5 ml) was stirred at 0 C. under argon atmosphere and a solution of 3-chloroperbenzoic acid (178 mg, 0.72 mmol) in dichloromethane (5 ml) was added slowly. After continuous stirring for 30 min and warming-up to r.t., stirring was continued for another 6 h. The reaction mixture was partitioned between dichloromethane and sodium bicarbonate (saturated aqueous solution) and extracted. The organic phase was washed with water, dried and the solvent was evaporated. The product was obtained after purification by silica gel chromatography using a heptane /ethyl acetate gradient as colorless waxy solid (86 mg, 77%). MS: M=309.0 (M+H)+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,74840-38-3, its application will become more common.

Reference:
Patent; Bleicher, Konrad; Flohr, Alexander; Groebke Zbinden, Katrin; Gruber, Felix; Koerner, Matthias; Kuhn, Bernd; Peters, Jens-Uwe; Sarmiento, Rosa Maria Rodriguez; US2011/306589; (2011); A1;,
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. 29274-24-6, name is 5-Chloropyrazolo[1,5-a]pyrimidine. A new synthetic method of this compound is introduced below., Computed Properties of C6H4ClN3

Preparation 1; The solution of 5-chloropyrazolo [ 1, 5-a] pyrimidine (200 mg) and trans-4-methoxycyclohexanamine (168 mg) in isopropylalcohol(2 ml) was refluxed for 3 hours. After cooling to ambient temperature, the reaction mixture was poured into water, then extracted with ethyl acetate . The organic layer was washed with brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel EPO elupsilonting with chloroform/methanol ( 100 : 0 to 100:10) to give N- (trans-4-methoxycyclohexyl)pyrazolo [1, 5-a] pyrimidin-5- amine (70 mg) .1H-NMR (DMSO-d6) 5:1.13-1.34 (4H,m) ,1-91-2.08 (4H,m) , 3.09-3.20 ( IH, m) ,3.33 (3H,s) , 3.70-3.86 (lH,m) ,5.95 (IH, d, J=2. OHz) ,6.19 (IH , d, J=7.6Hz) , 7.26(lH,d, J=7.4Hz) ,7.74 ( IH, d, J=2. OHz) , 8.41 (IH, d , J=7.6 Hz) . MS:247 (MH-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, 29274-24-6, 5-Chloropyrazolo[1,5-a]pyrimidine.

Reference:
Patent; ASTELLAS PHARMA INC.; WO2007/13673; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 160199-05-3, 2,4-Dichlorobenzo[4,5]thieno[3,2-d]pyrimidine, 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, 160199-05-3, blongs to pyrimidines compound. Computed Properties of C10H4Cl2N2S

General procedure: 2,4-dibromopyrimidine (CAS Registry Number: 3921-01-5) (24.46 g, 102.82 mmol) was added to a round bottom flask and dissolved in THF (360 ml)4,4,5,5-tetramethyl-2- (naphthalen-1-yl-ethyl) -1,3,2-dioxaborolane(CAS Registry Number: 1280709-91-2) (29.54 g, 113.11 mmol),Pd (PPh3) 4 (4.75 g, 4.11 mmol),K2CO3 (42.63 g, 308.47 mmol) and water (180 ml) were addedAnd stirred at 90 C.After the reaction was completed, the reaction mixture was extracted with CH 2 Cl 2 and water. The organic layer was dried over MgSO 4 and concentrated. The resulting compound was purified by silicagel column and recrystallized to obtain 18.03 g (yield: 60%) of the product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,160199-05-3, its application will become more common.

Reference:
Patent; Duksan Neolux Co.,Ltd.; Song Hyeon-ju; Park Mu-jin; Jeong Ho-yeong; Lee Mun-jae; Lee Seon-hui; Kwon Jae-taek; (49 pag.)KR2018/97955; (2018); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 7461-50-9, Adding some certain compound to certain chemical reactions, such as: 7461-50-9, name is 2-Chloropyrimidin-4-amine,molecular formula is C4H4ClN3, 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 7461-50-9.

A microwave reaction vessel was charged with 4-amino-2-chloropyrimidine (100 mg, 0.774 mmol, 1.0 eq), 2-methanesulfonyl-2-methylpropan-l -ol (353 mg, 2.33 mmol, 3.0 eq), and potassium carbonate (160.3 mg, 1.16 mmol, 1.5 eq) in propan-2-ol (1 mL). The reaction was stirred at room temperature for 1 min and heated under microwave irradiation at 200 C for 2.5 h (Biotage Initiator, maximum pressure set at 22 bar). The reaction mixture was cooled to room temperature and purified by chromatography on silica (solvent gradient: 0-10% 2M methanolic ammonia in ethyl acetate) to afford the title compound (163 mg, 86%). LCMS (ESI): [M+H]+ 246.3.

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. 7461-50-9, 2-Chloropyrimidin-4-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GENENTECH, INC.; BRYAN, Marian C.; CHAN, Bryan; DIEDERICH, Francois; DOTSON, Jennafer; HANAN, Emily; HEFFRON, Timothy; LAINCHBURY, Michael; HEALD, Robert; SEWARD, Eileen M.; WO2014/210354; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 611-08-5, 5-Nitrouracil, 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, name: 5-Nitrouracil, blongs to pyrimidines compound. name: 5-Nitrouracil

25 gm of 5-nitro uracil is suspended in 490 ml of phosphorous oxychloride for 10 minutes and diisopropyl ethylamine is slowly added to the suspension at room temp. The reaction suspension is refluxed at 130 oC for 3h. The solution is concentrated under reduced pressure to be a volume of 100 ml. Then the solution is added dropwise to 500 ml of ice water and stirred for 1h, and extracted with diethyl ether. The organic layer is washed with 500 ml of saturated ammonium chloride and dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Column chromatography on silica gel (ethyl acetate: Hexane=1:5) affords 16.8 gm of the title compound. White solid; mp:30-32 oC; IR (KBr): 1670, 1620, 1350, 785 cm-1; 1H NMR (400 MHz, CDCl3): delta 9.25 (s, 1H, H6) ppm; m/z=195(M+).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,611-08-5, 5-Nitrouracil, and friends who are interested can also refer to it.

Reference:
Article; Sadanandam; Jyothi; Adharvana Chari; Das, Parthasarathi; Mukkanti; Tetrahedron Letters; vol. 52; 42; (2011); p. 5521 – 5524;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 183438-24-6 , The common heterocyclic compound, 183438-24-6, name is 5-Bromo-2-iodopyrimidine, molecular formula is C4H2BrIN2, 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.

A mixture of potassium fluoride (1.77g) and cuprous iodide (5.79g) was stirred and heated together using a heat gun under vacuum (-1 mm) for 20min. After cooling, dimethyl formamide (20ML) and N-METHYL PYRROLIDINONE (20ML) were added followed by (trifluoromethyl) trimethylsilane (4. 1ML) and 5-BROMO-2-IODOPYRIMIDINE (6.5g). The mixture was stirred at rt for 5h and then the brown solution was poured into 6N ammonia solution. The product was extracted into ethyl acetate and the extracts were washed with sodium bicarbonate solution and brine and then dried (NA2SO4) and evaporated. Chromatography on silica gel (elution with 20-50% DICHLOROMETHANE in pentane) gave the title compound (D30) as a white solid (2. 4G). 1 H NMR (CDCI3) : 8.97 (2H, s).

The synthetic route of 183438-24-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2004/101546; (2004); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 111196-81-7, 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 111196-81-7 as follows.

Step 1: l-(5-ethylpyrimidin-2-yl)piperidin To a solution of piperidin-4-ol (2.55 g, 25.2 mmol) in MeCN (50 mL) was added 2-chloro-5-ethylpyrimidine (3.00 g, 21.0 mmol), followed by N-ethyl-N-isopropylpropan-2-amine (7 mL, 42.0 mmol) and the resulting reaction mixture was heated to 80C for 16 hrs. The mixture was diluted with water, extracted with EtOAc, washed with brine, dried over Na2S04, filtered and concentrated in vacuo. The residue was purified with column chromatography (CH2C12: EtOAc = 3:1 to 1:1) to afford the desired product (3.69 g, 85%) as a yellow solid.1H NMR (CDC13): delta 8.16 (2H, s), 4.37-4.42 (2H, m), 3.92-3.94 (1H, m), 3.24-3.30 (2H, m), 2.45 (2H, q, / = 7.6 Hz), 1.92-1.98(2H, m), 1.69 (1H, brs), 1.48-1.53 (2H, m), 1.19 (3H, t, / = 7.6 Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,111196-81-7, its application will become more common.

Reference:
Patent; CENTAURUS BIOPHARMA CO., LTD.; XIAO, Dengming; ZHU, Yan; HU, Yuandong; WANG, Huting; LIU, Yuliang; LI, Jijun; SUN, Deguang; WANG, Zhe; WEI, Yongheng; WANG, Zanping; TANG, Guojing; JING, Lutao; WO2012/103806; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 3764-01-0, 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 3764-01-0 as follows.

Under a nitrogen atmosphere, trichloropyrimidine (10 g, 54.5 mmol), phenylboronic acid (13.3 g, 109 mmol), palladium acetate (0.3 g, 1.37 mmol), triphenylphosphine (0.72 g, 2.73 mmol), dimethoxyethane (150 mL) and an aqueous solution of 2M sodium carbonate (170 mL) were added together in sequential order, and heated to reflux for eight hours. -After the reaction solution was cooled down to the room temperature, an organic phase was removed and an organic solvent was distilled away under reduced pressure. The obtained residue was refined by silica-gel column chromatography, whereby an intermediate 5-1 (9.2 g, a yield of 63%) was obtained.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3764-01-0, its application will become more common.

Reference:
Patent; IDEMITSU KOSAN CO., LTD.; Nishimura, Kazuki; Ogiwara, Toshinari; Hibino, Kumiko; Inoue, Tetsuya; Ito, Mitsunori; (130 pag.)US9711732; (2017); B2;,
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. 5750-74-3, name is 2,5-Dichloro-4-methoxypyrimidine. A new synthetic method of this compound is introduced below., Product Details of 5750-74-3

A solution of (2S,4R)-tert-butyl 4-amino-2-methylpyrrolidine-l-carboxylate (200 mg, 1.0 mmol), 2,5-dichloro-4-methoxypyrimidine (358 mg. 2.0 mmol) and K2C03 (226 mg, 2.0 mmol) in DMSO (10 mL) was stirred at RT for 2 hrs. The reaction mixture was diluted with water (30 mL) and extracted with EA (20 mL*3). The combined organic layers were washed with water (50 mL) and brine (50 mL), dried over Na2S04, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (PE:EA = 1 : 1) to afford (2S,4R)-tert-butyl 4-((5-chloro-4- methoxypyrimidin-2-yl)amino)-2-methylpyrrolidine-l-carboxylate (100 mg, 30%) as a white solid. [M+H] Calc?d for CisH^ClN^s, 343.1; Found, 343.1

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, 5750-74-3, 2,5-Dichloro-4-methoxypyrimidine.

Reference:
Patent; KINNATE BIOPHARMA INC.; KANOUNI, Toufike; ARNOLD, Lee D.; KALDOR, Stephen W.; MURPHY, Eric A.; TYHONAS, John; (0 pag.)WO2020/6497; (2020); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia