Tag: M.W:100-200

Reference of 5751-20-2, 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.5751-20-2, name is 2-(Methylthio)pyrimidin-4(3H)-one, molecular formula is C5H6N2OS, molecular weight is 142.18, as common compound, the synthetic route is as follows.

2-(Methylthio)pyrimidin-4(3H)-one (3 g, 21 mmol) and 4-aminobenzonitrile (2.99 g, 25 mmol) were weighed in a 50 mL round bottom flask.Nitrogen protection,Slowly warm up to 180 ¡ã C,Reaction 8h.After the reaction was cooled, it was sonicated by adding 20 mL of acetonitrile, filtered, and the filter cake was washed with acetonitrile, and the residue of 4-aminobenzonitrile was not detected by TLC, and the cake was dried to give a pale yellow solid which was 4-((4-oxo-1,6) – dihydropyrimidin-2-yl)amino)benzonitrile, yield 73.6percent,

The chemical industry reduces the impact on the environment during synthesis 5751-20-2, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Shandong University; Liu Xinyong; Zhou Zhongxia; Zhan Peng; (32 pag.)CN109369623; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 13223-25-1, 2-Chloro-4,6-dimethoxypyrimidine, 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, Recommanded Product: 2-Chloro-4,6-dimethoxypyrimidine, blongs to pyrimidines compound. Recommanded Product: 2-Chloro-4,6-dimethoxypyrimidine

A mixture of 2-chloro-4,6-dimethoxy-pyrimidine (3.35 g, 19.19 mmol, 1.0 equiv; commercially available) and 4-amino-piperidine-1-carboxylic acid tert-butyl ester (5.0 g, 24.94 mmol, 1.3 equiv; commercially available) in anhydrous DMF (100 mL) was heated to 100 C. for 48 h. The organic phase was concentrated under reduced pressure and the residue extracted with ethyl acetate (3*50 mL) from a solution of 1 M NaOH (100 mL). The combined organic phases were dried over MgSO4 and the product purified by silica column chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) eluding with a gradient of heptane/ethyl acetate providing 1.97 g (30%) of the title compound. MS (ISP): 339.3 [M+H]+.

The synthetic route of 13223-25-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Binggeli, Alfred; Christ, Andreas; Maerki, Hans-Peter; Martin, Rainer Eugen; US2007/225271; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 4270-27-3, 6-Chloropyrimidine-2,4(1H,3H)-dione, 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, Formula: C4H3ClN2O2, blongs to pyrimidines compound. Formula: C4H3ClN2O2

Compound 18a (5 g, 34 mmol) and sodium iodide (20 g) were dissolved in anhydrous DMF (50 ml.) and heated to reflux for 1.5 h (Ar atmosphere). The DMF was evaporated, and the solid residue dissolved in H2O (200 mL). The solution was stirred at RT for 4 h, a solid material was collected by vacuum filtration, and the solid was washed with H2O and dried. The solid was crystallized from EtOAc, providing compound 18b. 1H NMR (DMSO- Cf6) delta 6.03 (S, 1 H), 11.2 (s, 1 H), 11.6 (s, 1 H).

The synthetic route of 4270-27-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA, N.V.; MISKOWSKI, Tamara A.; WO2006/104713; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 4983-28-2 ,Some common heterocyclic compound, 4983-28-2, molecular formula is C4H3ClN2O, 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 (R)-tert-butyl 2-(hydroxymethyl)morpholine-4-carboxylate (605 mg, 2.79 mmol) in THF (5 mL) was added 2-chloropyrimidin-5-ol (200 mg, 1.532 mmol), triphenylphosphine (548 mg, 2.089 mmol) and DIAD (0.406 mL, 2.089 mmol) and the reaction was stirred at 20 ¡ãC under an atmosphere of nitrogen for 5 hours. The reaction was concentrated and resuspended in 1 mL DMSO, then was subjected directly to purification by flash chromatography (60g pre-packed C-18 SNAP cartridge: 35percent to 90percent acetonitrile (0.1percent formic acid) in water (0.1percent formic acid)). The desired fractions were combined and concentrated to afford the title compound (410 mg, 1.24 mmol, 89 percent yield). LCMS Method A RT= 1.01 min, ES+ve 274 (M+H-tBu).

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. 4983-28-2, 2-Chloro-5-hydroxypyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; CASILLAS, Linda N.; HARLING, John David; MIAH, Afjal Hussain; SMITH, Ian Edward David; RACKHAM, Mark David; (204 pag.)WO2017/182418; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 7355-55-7, 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 7355-55-7, name is 2-Amino-3,7-dihydropyrrolo[2,3-d]pyrimidin-4-one. This compound has unique chemical properties. The synthetic route is as follows.

Step 1. Creation of the heterocycle (FIG. 3). To a solution of 2,4-diamino-6-hydroxypyrimidine (1, 25.2 g) in DMF (480 mL) and water (80 mL) was added sodium acetate (27.2 g). The resulting yellow solution was stirred for 1 h. To the solution was added chloroacetaldehyde (50% solution, 25.4 mL) and the mixture was stirred at rt for 2 days. The volatiles were removed in vacuo and the residue was mixed with methanol (70 mL) and stored at rt overnight. The resulting solid was filtered. The solid was mixed with methanol (150 mL) and heated at 60 C. for 10 min and cooled to rt overnight. The resulting solid was filtered and dried. The yield of 2 was 15 g to 19 g. (0032) A mixture of 7-deazaguanine (14.2 g) and dimethylaniline (6 mL) in POCl3 (200 mL) was refluxed for 3 h (bath temp. 130 C.). After cooling to rt, volatiles were removed by distillation (bath temp 60 C.). The residue was mixed with water (2300 mL) and neutralized with ammonium hydroxide until complete precipitation of solid (pH4). The resulting precipitate was filtered and further purified by column chromatography (silica, MC_MeOH=10:1) to give 3.6 g (21.4 mmol, 23%) of solid (FIG. 3).

According to the analysis of related databases, 7355-55-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Benner, Steven A; Kim, Hyo-Joong; (15 pag.)US10059735; (2018); B1;,
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. 3001-72-7, name is 2,3,4,6,7,8-Hexahydropyrrolo[1,2-a]pyrimidine, molecular formula is C7H12N2, 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. Safety of 2,3,4,6,7,8-Hexahydropyrrolo[1,2-a]pyrimidine

Under carbon dioxide atmosphere, 0.2 mmol of 1,3-butadiyne 1b, 0.2 mmol of cesium carbonate, 0.6 mmol of DBN, 20mul of water, and 2 mL of acetonitrile were successively added to a Schlenk reaction tube, and the mixture was heated at 70 C in IKA and stirred for 24 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and the reaction solution was transferred with 20 mL of ethyl acetate. The reaction mixture was evaporated under reduced pressure and subjected to column chromatography to give the desired product 3b (63%).

With the rapid development of chemical substances, we look forward to future research findings about 3001-72-7.

Reference:
Patent; Henan Normal University; Liu Jianming; Yue Yuanyuan; Yan Xuyang; Zhao Shufang; (11 pag.)CN107954979; (2018); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 1820-81-1 ,Some common heterocyclic compound, 1820-81-1, molecular formula is C4H3ClN2O2, 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.

Method 19 2,4,5-Trichloropyrimidine 5-Chlorouracil (10.0 g, 68.5 mmol) was dissolved in phosphorus oxychloride (60 ml) and phosphorus pentachloride (16.0 g, 77 mmol) was added. The reaction mixture was then stirred at reflux (110 C.) for 16 hrs then allowed to cool to 20 C. The reaction mixture was then poured slowly and carefully into water (200 ml) at 25 C. with vigorous stirring. Then stirred well for 90 minutes before addition of EtOAc (250 ml). Organic layer separated off and aqueous layer re-extracted into EtOAc (250 ml). The organic layers were then combined and washed with sodium bicarbonate (200 ml aqueous solution), brine (200 ml) and then evaporated to a yellow liquid. The crude material was purified by column chromatography eluding with dichloromethane to afford the product as a yellow liquid (6.37 g, 51%). NMR (CDCl3): 8.62 (s, 1H); MS (M+): 182, 184,186.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1820-81-1, its application will become more common.

Reference:
Patent; Pease, Elizabeth Janet; Breault, Gloria Anne; Morris, Jeffrey James; US2003/149064; (2003); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 25940-35-6, Pyrazolo[1,5-a]pyrimidine-3-carboxylic acid, 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, Safety of Pyrazolo[1,5-a]pyrimidine-3-carboxylic acid, blongs to pyrimidines compound. Safety of Pyrazolo[1,5-a]pyrimidine-3-carboxylic acid

To the mixture of pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (42 mg, 0.26 mmol) and diisopropylethylamine (0.09 mL, 0.52 mmol) in DMF (2 mL) was added 2-(7-aza-1H- benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (131 mg, 0.34 mmol) then the mixture was stirred at 25 oC for 15 min. To the mixture was added a solution of 2-[4-(5- amino-2,2-dimethyl-3H-benzofuran-6-yl)piperazin-1-yl]ethanol (50 mg, 0.17 mmol) in DMF (2 mL) and the resulting mixture was stirred at 25 oC for 16h. The mixture was purified by preparative HPLC(Xbridge 21.2*250 mm c18, 10um, A: acetonitrile 10-70%; B:10 mM ammonium bicarbonate in water) to afford N-[6-[4-(2-hydroxyethyl)piperazin-1-yl]-2,2- dimethyl-3H-benzofuran-5-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide (45 mg, 60%) as a yellow solid.1H NMR (400 MHz,DMSO-d6) delta 10.42(s, 1H), 9.37(dd, J = 1.6 , 7.2Hz, 1H), 8.92 (dd, J = 1.6, 4.4Hz, 1H), 8.68(s, 1H), 8.31(s, 1H), 7.36(dd, J = 4.4,7.2Hz, 1H), 6.69(s, 1H), 4.45(t, J =5.2Hz, 1H), 3.54(q, J = 5.6 Hz, 2H), 3.00(s, 2H), 2.84-2.78(m, 4H), 2.74-2.61 (m, 4H), 2.50(t, J = 5.6 Hz ,2H), 1.41(s, 6H). MS (ESI): m/z = 437.3 [M+1]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,25940-35-6, Pyrazolo[1,5-a]pyrimidine-3-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BRYAN, Marian, C.; GOBBI, Alberto; KIEFER, James, Richard, Jr.; KOLESNIKOV, Aleksandr; OLIVERO, Alan, G.; DROBNICK, Joy; LIANG, Jun; RAJAPAKSA, Naomi; (846 pag.)WO2017/108723; (2017); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 5750-76-5, 2,4,5-Trichloropyrimidine, 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, 5750-76-5, blongs to pyrimidines compound. Computed Properties of C4HCl3N2

To a 250 mL round bottom flask equipped with a stir bar was added 1 g 5-chloro- 2,4-dichloro- pyrimidine, and l5mL of diethyl ether. The mixture was cooled to 0C inan ice bath and then 1 equivalent of sodium methoxide in methanol (prepared from reacting 120 mg of sodium with 4 mL of methanol at room temperature) was slowly added. The reaction was stirred over night at room temperature and checked by LCMS. The white precipitate was filtered and the solid washed with cold methanol. After drying, 0.98 g of pure 2,5-dichloro-4-methoxypyrimidine was obtained and this material wasused without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5750-76-5, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BAKER-GLENN, Charles; CHAMBERS, Mark; CHAN, Bryan K.; ESTRADA, Anthony; SWEENEY, Zachary Kevin; WO2013/79495; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 4316-98-7, 6-Chloro-4,5-diaminopyrimidine, 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, Application In Synthesis of 6-Chloro-4,5-diaminopyrimidine, blongs to pyrimidines compound. Application In Synthesis of 6-Chloro-4,5-diaminopyrimidine

1.6 g of the 2-(N-methylmethylsulfonamide)nicotinic acid obtained in this way are suspended in 10 ml of dichloromethane, and 0.6 ml of thionyl chloride is added dropwise. This suspension is stirred at 40 C. for 3 h, and, immediately after addition of a few drops of DMF, 3 is reacted further with 1 g of 6-chloropyrimidine-4,5-diamine at RT for 16 h. Removal of the solvent gives a 1:3 mixture of 2.3 g of the regioisomers 4, which are immediately reacted further in 30 ml of POCl3 at 50 C. in 48 h to give 5. Chromatography with dichloromethane/methanol=100:0->90:10 gives 810 mg of a colourless solid; LCMS: 339.0 (M+H), RT. 1.341 min.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,4316-98-7, 6-Chloro-4,5-diaminopyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; MERCK PATENT GMBH; Heinrich, Timo; Rohdich, Felix; Esdar, Christina; Krier, Mireille; Greiner, Hartmut; US2015/218155; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia