Tag: M.W:200-300

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

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

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

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

Electric Literature of 39551-54-7, 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. 39551-54-7, name is 2,4-Dichloropyrido[3,2-d]pyrimidine, molecular formula is C7H3Cl2N3, 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.

2,4,-dichloropyrido[3,2-d]pyrimidine (80 mg, 0.39 mmol, 1 equiv.) was treated with THF (10 ml) followed by N,N-diisopropylethylamine (0.28 mL, 1.5 mmol, 4 equiv.), and then (R)-methyl 2-amino-5,5-difluorohexanoate 79C (110 mg, 0.39 mmol, 1 equiv., TFA salt). The reaction mixture was stirred for 1 h to form 79D and then this solution was used directly. LCMS (m/z): 345.11 [M+H]+; tR=1.09 min. on LC/MS Method A.

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 39551-54-7, 2,4-Dichloropyrido[3,2-d]pyrimidine.

Reference:
Patent; Gilead Sciences, Inc.; Aktoudianakis, Evangelos; Chin, Gregory; Mackman, Richard L.; Metobo, Samuel E.; Mish, Michael R.; Pyun, Hyung-jung; Zablocki, Jeff; (175 pag.)US2016/289229; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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.573675-29-3, name is 7-Bromopyrido[3,2-d]pyrimidin-4(3H)-one, molecular formula is C7H4BrN3O, molecular weight is 226.0302, as common compound, the synthetic route is as follows.category: pyrimidines

7-Bromopyrido[3,2-d]pyrimidin-4-ol (1.02 g, 4.51 mmol) was suspended in dry toluene (80 mL) under nitrogen. Phosphorus oxychloride (5.0 mL, 54.6 mmol) was added and the mixture heated to reflux under nitrogen. After 5 hours the reaction was cooled to RT. The solution was placed in a water bath and saturated sodium bicarbonate (50 mL) was added slowly with strong stirring. After 45 minutes the phases were separated and the organic evaporated to dryness under reduced pressure. The crude 7-bromo-4-chloropyrido[3,2-d]pyrimidine (0.46 g, 1.89 mmol, 42% yield) was used without further purification. 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 8.59 (d, J=1.96 Hz, 1H) 9.11-9.15 (m, 2H). LC/MS (ESI+) m/z=243.8 (M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,573675-29-3, 7-Bromopyrido[3,2-d]pyrimidin-4(3H)-one, and friends who are interested can also refer to it.

Reference:
Patent; LEWIS, Richard T.; ALLEN, Jennifer R.; BROWN, James; GUZMAN-PEREZ, Angel; HUA, Zihao; JUDD, Ted; LIU, Qingyian; OLIVIERI, Philip R.; ROMERO, Karina; SCHENKEL, Laurie; STELLWAGEN, John; WHITE, Ryan; US2015/38497; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 7400-06-8 , The common heterocyclic compound, 7400-06-8, name is 6-Amino-5-(2,2-diethoxyethyl)pyrimidin-4-ol, molecular formula is C10H17N3O3, 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.

Step2 7H-Pyrrolo[2,3-d]pyrimidine-4-ol12.8M Hydrochloric acid (1.2 ml) was added to a suspension of 6-Amino-5-(2,2-diethoxy- ethyl)-pyrimidin-4-ol (2.23g 9.8 mmol) in water (60 ml) was stirred at ambient temperature for 2.5 hrs. The mixture was then cooled with an ice water bath and then filtered. The filtered solids were dried in vacuo to afford title compound as a yellow solid 1.2g (90percent).LC/MS: RT = 0.572 min; m/z = 158 [M+Na]+. Total run time 3.75 mins. 1H NMR (dbeta DMSO): delta 6.40 (dd, 1H); 7.03 (dd, 1 H); 7.82 (s, 1H); 11.74 (brs, 1H); 11.83 (brs, 1H).

The synthetic route of 7400-06-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERNALIS (R & D) LTD.; WO2007/104944; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 38275-48-8, 5-Bromo-2-(methylsulphonyl)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, category: pyrimidines, blongs to pyrimidines compound. category: pyrimidines

Under Ar(g), to a mixture of pyrazin-2-amine (1) (209mg, 2.2mmol), 5- bromo-2-(methylsulfonyl)pyrimidine (2) (474mg, 2.0mmol), Cs2C03 (1.30g, 4.0mmol) was added degassed dry 1 ,4-dioxane (13ml_). The reaction mixture was then flushed with Ar(g) for 1 min before Pd2(dba)3 (92mg, 0.1 mmol) and Xantphos (127mg, 0.22mmol) were added. The reaction mixture was heated up to 90C for 40h. It was then cooled down to rt. EtOAc (15ml_), H20 (10mL) and brine (5mL) were added to the reaction mixture. The organic phase was separated and the aqueous phase was extracted with EtOAc (15ml_). The organic layers were combined and Pd-scavenger (MP-TMT, ~400mg, 1.3mmol/g) was added. This was shaken for several hours followed by filtration. The filtrate was concentrated in vacuo, dissolved in DMSO (4ml_) and purified by basic prep LCMS to yield (3) as a solid (13.5mg, 3%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,38275-48-8, 5-Bromo-2-(methylsulphonyl)pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; KARUS THERAPEUTICS LIMITED; SHUTTLEWORTH, Stephen Joseph; GATLAND, Alice Elizabeth; FINNEMORE, Daniel John; ALEXANDER, Rikki Peter; SILVA, Franck; CECIL, Alexander; (233 pag.)WO2019/166824; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 59549-51-8, 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. 59549-51-8, name is 5-Bromo-2-chloro-4-(methylthio)pyrimidine. A new synthetic method of this compound is introduced below.

5-Bromo-2-chloro-4-(methylthio)pyrimidine (125 mmol, 30 g) was suspended in n-BuOH (300 mL) with 3-chloro-4-fluoroaniline (125 mmol, 18.22 g). The reaction was then treated with 4 N HCl (100 mmol, 25 niL) in dioxane and refluxed at 100 0C for 1.5 h under nitrogen. The reaction was cooled to room temperature, diluted with diethyl ether and the solid was filtered and dried to afford 29 g of (5-bromo-4-methylsulfanyl-pyrimidin-2-yl)-(3-chloro-4- fluoro-phenyl)-amine as a pale yellow solid (83 mmol, 67 %). MS(ES): 348(M) and 350(M+2) for CnH8BrClFN3S.1H-NMR 300MHz DMSO-d6 : delta 2.55 (s, 3H), 7.34 (t, J= 9.0 Hz, IH), 7.56-7.59 (m, IH), 8.08 (t, J= 4.5 Hz, IH), 8.33 (s, IH), 9.98 (s, IH).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,59549-51-8, 5-Bromo-2-chloro-4-(methylthio)pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; BORIACK-SJODIN, Ann; CARCANAGUE, Daniel, Robert; DUSSAULT, Daemian, David; HATOUM-MOKDAD, Holia; HULL, Kenneth, Gregory; IOANNIDIS, Georgine; MANCHESTER, John, Irvin; McGUIRE, Helen, Maureen; McKINNEY, David, Charles; STOKES, Suzanne; WO2010/38081; (2010); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 696-07-1 ,Some common heterocyclic compound, 696-07-1, molecular formula is C4H3IN2O2, 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.

5-Iodouracil (23.8 g), TEA (30.3 g), Tol (240 mL) were placed in a 500 mL three-necked flask and heated to 100 C.When the internal temperature of the bottle reached 90 C, phosphorus oxychloride (33.7 g) was slowly added dropwise.After the addition was completed, the temperature was kept stirring for 1 h, then cooled to room temperature, suction filtered, and the filtrate was collected.The solid was washed with PE/EA=5/1, and the filtrate and washing solution were combined.Spin dry to obtain a crude product and then beat with PE to give the product 24.5 g of an off-white solid.The yield was 89%.

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. 696-07-1, 5-Iodouracil, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Beijing Ruiboao Biological Technology Co., Ltd.; Liu Zhiqiang; Li Yazhou; Chen Zhenchang; Zhang Hongjuan; (7 pag.)CN109761914; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia