Tag: M.W:100-200

Electric Literature of 1209459-16-4, Adding some certain compound to certain chemical reactions, such as: 1209459-16-4, name is 2-Bromopyrimidine-4-carbonitrile,molecular formula is C5H2BrN3, 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 1209459-16-4.

Example 11. Preparation of (3S)-tert-butyI 3-((l-(2-chIorophenyl)-2-((3,3- difluorocyclobutyl) amino)-2-oxoethyl)(3,5-difluorophenyl)carbamoyl)-4-(4- cyanopyrimid -2-yl)-5-oxopiperazine-l-carboxylate (racemic) – Compound 98 A mixture of (3S)-tert-butyl3-((l -(2-chlorophenyl)-2-((3,3-difluorocyclobutyl)amino)-2-oxoethyl) (3,5-difluorophenyl)carbamoyl)-5-oxopiperazine-l-carboxylate (200 mg, 0.326 mmol), 2- bromopyrimidine-4-carbonitrile (0.489 mmol), Pd2(dba)3 (30.2 mg, 0.0323 mmol), XantPhos (19.1 mg, 0.03 mmol) and Cs2C03 (148.7 mg, 0.46 mmol) in 1,4-dioxane (10 mL) was stirred at 80 C for 3 hr under N2. The reaction mixture was cooled to room temperature and filtered. The filtrate was concentrated and the residue was purified by a standard method to afford the desired product. NMR (400 MHz, CDC13): delta 8.97 (d, J= 4.3 Hz, 1H), 7.85-7.55 (d, 1H), 7.51-7.39 (m, 2H), 7.25 (t, J= 7.6 Hz, 1H), 7.13-6.26 (m, 6H), 5.91 (d, J= 7.6 Hz, 1H), 4.92-4.08 (m, 5H), 3.38 (t,J= 14.9 Hz, 1H), 3.02 (s, 2H), 2.83-2.22 (d, 2H), 1.61 (s, 9H). MS : 716.1 (M+l)+.

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. 1209459-16-4, 2-Bromopyrimidine-4-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AGIOS PHARMACEUTICALS, INC.; LEMIEUX, Rene M.; POPOVICI-MULLER, Janeta; TRAVINS, Jeremy M.; CAI, Zhenwei; CUI, Dawei; ZHOU, Ding; WO2015/10297; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 29274-24-6 ,Some common heterocyclic compound, 29274-24-6, molecular formula is C6H4ClN3, 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 8; 5-Chloropyrazolo [1, 5-a] pyrimidine (100 mg) andN-iodosuccinimide (161 mg) in N, N-dimethylformamide (ImI) was stirred at ambient temperature for 4 hours. The reaction mixture was poured into a mixture of 10% sodium thiosulfate aqueous solution and chloroform. Then the organic layer was washed with saturated NaHCU3 aqueous solution, water, brine, dried over magnesium sulfate, and evaporated in vacuo. Resulting precipitates were collected by filtration and washed with diisopropyl ether to give 5-chloro-3-iodopyrazolo [ 1, 5-a] pyrimidine as an brown solid (180 mg) .1H-NMR(DMSO-d6)delta:7.42 ( IH, d, J=9.5Hz) , 7.97 ( IH, s) , 8.23 ( IH, d, J=9.2Hz) . MS:279 (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,29274-24-6, its application will become more common.

Reference:
Patent; ASTELLAS PHARMA INC.; WO2007/13673; (2007); 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. 35144-22-0, name is 4,6-Dimethyl-2-methylsulfonylpyrimidine. A new synthetic method of this compound is introduced below., Safety of 4,6-Dimethyl-2-methylsulfonylpyrimidine

Example 35 76 mg of 5-isopropyl-N-[6-(4-(4,6-dimethyl-2-pyrimidinyloxy)-2-butynyloxy)-5-(o-methoxyphenoxy)-2-methyl-4-pyrimidinyl]-2-pyridine sulfonamide was obtained as a colourless foam starting from 80 mg of 5-isopropyl-N-[6-(4-hydroxy-2-butynyloxy)-5-(o-methoxyphenoxy)-2-methyl-4-pyrimidinyl]-2-pyridine sulfonamide (Example 7d) and 75 mg of 4,6-dimethyl-2-methylsulfonylpyrimidine following the procedure given in Example 17. LC-MS: tR=5.51 min, [M+1]+=605.35, [M-1]-=603.43.

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, 35144-22-0, 4,6-Dimethyl-2-methylsulfonylpyrimidine.

Reference:
Patent; Bolli, Martin; Boss, Christoph; Clozel, Martine; Fischli, Walter; US2003/87920; (2003); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 3934-20-1, Adding some certain compound to certain chemical reactions, such as: 3934-20-1, name is 2,4-Dichloropyrimidine,molecular formula is C4H2Cl2N2, 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 3934-20-1.

Into a 50-mL round-bottom flask, was placed 2,4-dichloropyrimidine (1.1 g, 7.38 mmol, 1.00 equiv.), methanamine hydrochloride (498 mg, 7.38 mmol, 1.00 equiv.), potassium carbonate (3.07 g, 22.21 mmol, 3.00 equiv.), N,N-dimethylformamide (10 mL). The resulting solution was stirred for 18 h at 20 C. The resulting solution was diluted with 60 mL of H2O. The resulting solution was extracted with 3×80 mL of ethyl acetate and the organic layers combined. The resulting mixture was washed with 3×100 mL of brine. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1/2). This resulted in 0.67 g (63%) of 2-chloro-N- methylpyrimidin-4-amine as a white solid.

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. 3934-20-1, 2,4-Dichloropyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; EPIZYME, INC.; CAMPBELL, John Emmerson; DUNCAN, Kenneth William; FOLEY, Megan Alene; HARVEY, Darren Martin; KUNTZ, Kevin Wayne; MILLS, James Edward John; MUNCHHOF, Michael John; (586 pag.)WO2017/181177; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 6972-27-6, 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. 6972-27-6, name is 6-Chloro-1,3-dimethylpyrimidine-2,4(1H,3H)-dione. A new synthetic method of this compound is introduced below.

General procedure: A mixture of (18a) (69 mg, 0.176 mmol), 6-chloro-1,3-dimethylpyrimidine-2,4(1H,3H)-dione (61 mg, 0.35 mmol) and diisopropylethylamine (0.152 mL, 0.880 mmol) in isopropyl alcohol (0.5 mL) was heated at 80 C for 7 h. The reaction mixture was diluted with ethyl acetate, washed with satd NaHCO3 and brine, dried over NaSO4, and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (AcOEt/hexane, and then MeOH/CHCl3) to give methyl 2-(11-(3-(4-(1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)piperazin-1-yl)propylidene)-6,11-dihydrodibenzo[b,e]oxepin-2-yl)acetate (87 mg, 93% yield) as amorphous.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,6972-27-6, its application will become more common.

Reference:
Article; Kubota, Katsumi; Kurebayashi, Hirotaka; Miyachi, Hirotaka; Tobe, Masanori; Onishi, Masako; Isobe, Yoshiaki; Bioorganic and Medicinal Chemistry; vol. 19; 9; (2011); p. 3005 – 3021;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 1194-21-4, 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.1194-21-4, name is 2-Amino-6-chloropyrimidin-4(3H)-one, molecular formula is C4H4ClN3O, molecular weight is 145.55, as common compound, the synthetic route is as follows.

6-Amino-4-chloropyrimidin-2(1H)-one (3, 200 mg, 0.84 mmol) and 2-methyl-5-nitroaniline (627 mg, 2.52 mmol) were heated at 170 C for 3 h. The mixture was then cooled to rt and diethyl ether was added. The mixture was sonicated for 5 min. The suspension was filtered, and the filter cake was dissolved in MeOH and purified by column chromatography (silica gel, dichloromethane/methanol 9:1 v/v) to afford 4 (128 mg, 60%) as a brown solid.

Statistics shows that 1194-21-4 is playing an increasingly important role. we look forward to future research findings about 2-Amino-6-chloropyrimidin-4(3H)-one.

Reference:
Article; Kim, Hee Jin; Oh, Chang-Hyun; Yoo, Kyung Ho; Bulletin of the Korean Chemical Society; vol. 34; 8; (2013); p. 2311 – 2316;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 4316-93-2, Adding some certain compound to certain chemical reactions, such as: 4316-93-2, name is 4,6-Dichloro-5-nitropyrimidine,molecular formula is C4HCl2N3O2, 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 4316-93-2.

6-Chloro-5-nitropyrimidin-4-amine[00161] A solution of 28% aqueous ammonium hydroxide (670 mL, 5.35 mol, 1.04 equiv) was added in a drop-wise fashion to a rapidly stirred solution of the 4,6-dichloro-5- nitropyrimidine solid (1000 g, 5.16 mol, 1.00 equiv) in diethyl ether (4000 mL) and methanol (670 mL). The addition was carried out over a period of 2 hours. Upon completion of addition, the resulting yellow solid was filtered off, washed with water and hexane, and dried under reduced pressure to give the title compound as a yellow solid (yield: 675 g). This crude solid was used in the next step without any further purification. NMR (400 MHz, DMSO- d6): delta 8.97 (s, 1H), 7.91 (broad s, 2H). MS (EI) for C4H3CIN4O2: 175 (MH+).

According to the analysis of related databases, 4316-93-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; EXELIXIS, INC.; PATRICK, Kearney; WO2012/37226; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 7752-82-1 , The common heterocyclic compound, 7752-82-1, name is 5-Bromopyrimidin-2-amine, molecular formula is C4H4BrN3, 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.

To a solution of 2-amino pyridine (30 g, 0.31 mol) in DME (120 mL) was added chloro acetone (40.5 mL, 0.47 mol) at room temperature. The reaction mixture was heated to reflux, and then stirred for 48 hours. The volatiles were concentrated under reduced pressure. Then the residue was purified by column chromatography eluting with 1% MeOH/DCM to afford Int-2 (20 g, 48%) as a liquid. Mass (m/z): 133 [M++1]. 1H NMR (200 MHz, dmso-d6): delta8.05 (d, J=8.2 Hz, 1H), 7.35 (s, 1H), 7.1 (t, J=6.8 Hz, 1H), 6.7 (t, J=6.8 Hz, 1H), 6.5 (d, J=8.2 Hz, 1H), 2.45 (s, 3H). To a solution of Int-2 (10 g, 76.7 mmol) in acetonitrile (50 mL) was added N-iodo succinamide (20.4 g, 80 mmol) portion wise at room temperature and then stirred for 48 hours. The precipitated solid was filtered off. The crude material was re-crystallized from ethyl acetate/water to afford Int-3 (9 g, 49%) as solid. Mass (m/z): 259 [M++1]. 1H NMR (200 MHz, dmso-d6): delta 8.22 (d, J=8 Hz, 1H), 7.47 (d, J=7.2 Hz, 1H), 7.29 (t, J=7.0 Hz, 1H), 2.35 (s, 3H). To a solution of Int-3 (6.0 g, 29.2 mmol) in IPA-H2O (75 mL, 2:1) was added PdCl2(dppf).DCM (4.7 g, 5.8 mmol), followed by the addition of tert-butyl amine (3.1 g, 43.8 mmol) at room temperature and the resulting reaction mixture was degassed for 15 minutes. Then Int-4 (2.9 g, 18.6 mmol) was added to the reaction mixture at room temperature. The reaction mixture was heated to 100 C. and then stirred for 16 hours. The reaction mixture was diluted with water (100 mL), extracted with EtOAc (3¡Á100 mL), washed with water, brine and dried over anhydrous Na2SO4. The organic layer was concentrated under reduced pressure. The crude material was purified by column chromatography eluting with 1% MeOH/DCM to afford Int-5 (1.6 g, 28%). Mass (m/z): 244 [M++1]. 1H NMR (200 MHz, dmso-d6): delta 8.51 (t, J=5 Hz, 2H), 7.71 (s, 1H), 7.63-7.55 (m, 2H), 7.34 (t, J=7 Hz, 1H), 6.94 (t, J=7 Hz, 1H), 2.43 (s, 3H). To a stirred mixture of 5-bromo 2-aminopyrimidine (8 g, 45.97 mmol) in MeOH-CH3CN (200 mL) in a steel bomb were added Pd(CH3CN)2Cl (2.38 g, 9.19 mmol), racemic-BINAP (5.7 g, 9.19 mmol), DIPEA (10.4 mL, 53.7 mmol) at room temperature and then closed the steel vessel tightly. Then CO gas (100 psi) was purged into the steel bomb and the stirring was continued at 120 C. for 45 hours. The reaction mixture was allowed to room temperature. The reaction mixture was filtered through a pad of celite. The celite pad was washed with excess of methanol and the filtrate was concentrated under vacuum. The crude material was purified by column chromatography eluting with 0.75% MeOH/DCM to afford Int-6 (5 g, 71%) as solid. Mass (m/z): 154 [M++1]. 1H NMR (200 MHz, dmso-d6): delta 8.65 (s, 3H), 7.49 (brs, 2H), 3.58 (s, 3H) To a stirred mixture of Int-5 (3 g, 2.34 mmol) and Int-6 (1.8 g, 12.34 mmol) in 1,4-dioxane (90 mL) were added Pd(OAc)2 (279 mg, 1.23 mmol) and Xanthpos (710 mg, 1.23 mmol) followed by cesium carbonate (6 g, 18.5 mmol) at room temperature. The resulting mixture was degassed and stirred at reflux temperature for 30 hours. The reaction mixture was cooled to room temperature and then stirred for 15 minutes. The precipitated solids were filtered off, washed with water (2¡Á10 mL) and dried under vacuum. The crude material was purified by column chromatography eluting with 1.5% MeOH/DCM to afford Int-7 (0.6 g, 13.6%) as solid. Mass (m/z): 361.2 [M++1]. 1H NMR (500 MHz, dmso-d6): delta 10.76 (brs, 1H), 8.97 (s, 2H), 8.56 (d, J=7, 1H), 8.47 (d, J=5.5 Hz, 1H), 8.38 (s, 1H), 7.58 (d, J=9.5 Hz 1H), 7.34-7.29 (m, 2H), 6.99 (t, J=76 Hz, 1H), 3.84 (s, 3H), 2.46 (s, 3H). To a stirred solution of Int-7 (0.5 g, 1.38 mmol) in MeOH-CH3CN (1:2, 25 mL) was added aqueous NH2OH solution (15 mL) at 0 C. After being stirred for 20 minutes at the same temperature, NaOH (0.44 g, 11.10 mmol) in water (1 mL) was added drop wise to the reaction mixture at 0 C. The reaction mixture was warmed to room temperature and stirred for 2 days. The volatiles were concentrated under vacuum and the obtained residue was diluted with water and neutralized to about pH 7 with 2 N HCl at 0 C. The precipitated solids were filtered off, washed with water (2¡Á10 mL) and dried under vacuum to afford the title compound (0.4 g, 80%) as off-white solid. Mass (m/z): 362.1 [M++1]. 1H NMR (200 MHz, dmso-d6): delta 11.2 (bs, 1H), 10.5 (s, 1H), 9.12 (bs, 1H), 8.84 (s, 2H), 8.57 (d, J=7.0 Hz, 1H), 8.45 (d, J=5.0 Hz, 1H), 8.38 (s, 1H), 7.58 (d, J=9.0 Hz, 1H), 7.32 (t, J=7.5 Hz, 1H), 7.25 (d, J=4.0 Hz, 1H), 6.98 (d, J=7.0 Hz, 1H), 2.49 (s, 3H). 13C NMR (125 MHz, dmso-d6): delta 160.7, 157.1, 153.0, 148.7, 144.5, 142.3, 137.9, 125.2, 123.9, 118.8, 118.2, 117.0, 116.6, 112.7, 112.4, 14.3.

The synthetic route of 7752-82-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Melvin, JR., Lawrence S.; Graupe, Michael; Venkataramani, Chandrasekar; US2010/29638; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 13036-50-5, 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.13036-50-5, name is 2-Chloro-4-phenylpyrimidine, molecular formula is C10H7ClN2, molecular weight is 190.629, as common compound, the synthetic route is as follows.

Example 37 2-(4-(4-phenylpyrimidin-2-ylamino)phenyl)acetamidePart I: 2-(4-(4-phenylpyrimidin-2-ylamino)phenyl)acetic acidGeneral Procedure I: Microwave assisted halogen displacement with amino group [0166] A mixture of 2-chloro-4-phenylpyrimidine (0.19 g, 1.0 mmol), 2-(4- aminophenyl)acetic acid (0.38 g, 2.5 mmol), diisopropylethylamine (0.38 mL, 2.0 mmol), THF (3.0 mL) and water (1.0 mL) was placed in a seal tube and heated up to 160C in a microwave (Biotage, Model: Initiator) for 1O h. The reaction mixture was diluted with ether and washed with brine. The organic layer was separated, dried (MgSO4), and concentrated to afford 2-(4-(4-phenylpyrimidin-2-ylamino)phenyl)acetic acid in 77% yield. MS (ESI) 306 (M+H).

Statistics shows that 13036-50-5 is playing an increasingly important role. we look forward to future research findings about 2-Chloro-4-phenylpyrimidine.

Reference:
Patent; THE SCRIPPS RESEARCH INSTITUTE; WO2009/32861; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 155-10-2, 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. 155-10-2, name is 4-Amino-2-chloro-5-fluoropyrimidine, molecular formula is C4H3ClFN3, 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.

10287] 0.15 g (1.01 mmol) of 2-chloro-5-fluoropyrimi- dine-4-amine, 0.249 g (1.22 mmol) of (2-methyl-4,5,6,7- tetrahydrobenzothiophen-4-yl)ammonium chloride and 0.63 g (0.68 ml, 3.05 mol) of dicyclohexylethylamine in 2.0 ml of 1-methyl-2-pyrrolidone are heated at 180 C. in a closed cuvette in the microwave for 90 minutes (l3iotage Initiator, http://www.biotage.comlproduct-page/biotage-initiator).The crude mixture thus obtained is applied to silica gel and purified by column chromatography with heptane/ethyl acetate as mobile phase. Concentration gives 0.072 g of 5-fluoro-N2-(2-methyl-4,5,6,7-tetrahydro- 1 -benzothiophen-4-yl)pyrimidine-2,4-diamine (in waxy form) (22% yield at 85% purity).

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 155-10-2, 4-Amino-2-chloro-5-fluoropyrimidine.

Reference:
Patent; Bayer CropScience Aktiengesellschaft; JAKOBI, Harald; MINN, Klemens; BUSCATO ARSEQUELL, Estella; DIETRICH, Hansjoerg; GATZWEILER, Elmar; ROSINGER, Christopher Hugh; SCHMUTZLER, Dirk; (44 pag.)US2018/213780; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia