Pyrimidines

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 591-55-9, name is 5-Aminopyrimidine, the common compound, a new synthetic route is introduced below. SDS of cas: 591-55-9

A mixture of 5-ethyl-6-oxo-6, 7-dihydro-5H-1-oxa-s-indacene-7-carboxylic acid ethyl ester (150 mg. 0.6 mmol) and 5-aminopyrimidine (52 mg, 0.6 mmol.) in benzene (40 ml) was refluxed over a Dean-Stark trap for 1 hour. The mixture was cooled to room temperature, diluted with hexanes and the resulting precipitate filtered. The filtrant was dissolved in ethyl acetate (75 ml) and methanol (3 mi) and washed with 1N hydrochloric acid (1 X 5 ml), brine (1 X 5 ml), dried (sodium sulfate) then concentrated in vacuo. The residue was dissolved in methylene chloride (2 ml), diluted with diethyl ether (5 mi) and triturated with hexanes to give 54 mg 5-ethyl-6- oxo-6, 7-dihydro-5H-1-oxa-5-aza-s-indacene-7-carboxylic acid pyrimidin-5-ylamide (31%) as an orange solid, mp 100-3 C.’H-NMR (CDCI3) : No. 8.9 (s, 1H), 8.6 (d, 1H), 8.1 (d, 1H), 7.9 (s, 1H), 7.7 (s, 1H), 7.1 (s, 1H), 6.8 (s, 1H), 4.5 (s, 1H), 3.9 (q, 2H), 1.3 (t, 3H). MS (m/z, %): 321 (M+-1, 100).

The synthetic route of 591-55-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2005/41957; (2005); A1;,
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Related Products of 99586-66-0 ,Some common heterocyclic compound, 99586-66-0, molecular formula is C6H5ClN4, 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 this example, two different synthesis reactions were performed subsequently in one reaction vessel without exchange of the reaction medium. (0077) 5.0 g (1 1 .3 mmol) of 5-bromo-6-fluoro-2-((2S,4S)-4-hydroxypyrrolidin-2-yl)-3- phenylquinazolin-4(3/-/)-one hydrochloride and 1 .9 g (12.5 mmol / 1 .1 eq.) of (2- methoxypyrimidin-5-yl)boronic acid was provided in a reaction mixture comprising 5.0 mol% PdCI2(dtbpf) and 3.0 eq. NMM in 40 ml (8V) 2% TPGS-750-M in water and 20 ml (4V) THF. The reaction mixture formed a stable emulsion and the reaction was allowed to proceed for 16 h at 50C under stirring. Then 1 .7 g (10.2 mmol / 0.9 eq.) of 2-amino- 4-chloro-6-methylpyrimidine-5-carbonitrile in 10 ml (2V) THF were added to the reaction mixture. After 18 h at room temperature the product 2-amino-4-((2S,4S)-2-(6- fluoro-5-(2-methoxypyrimidin-5-yl)-4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)-4- hydroxypyrrolidin-1 -yl)-6-methylpyrimidine-5-carbonitrile was obtained. (0078) (0079) The same reaction performed in conventional organic solvent (e.g. N- methylpyrrolidone) resulted in about 30% side product (structure in bracket) of the Suzuki cross-coupling reaction. This could be reduced to 3% with the use of 2% TPGS- 750-M in water as solvent and THF as co-solvent.

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. 99586-66-0, 2-Amino-4-chloro-6-methylpyrimidine-5-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; GALLOU, Fabrice; PARMENTIER, Michael; ZHOU, Jianguang; GUO, Pengfei; (27 pag.)WO2017/168303; (2017); A1;,
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Electric Literature of 42754-96-1, 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. 42754-96-1, name is 4,6-Dichloro-1H-pyrazolo[3,4-d]pyrimidine, molecular formula is C5H2Cl2N4, 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 solution of 4-(1H-benzimidazol-2-yl)-phenylamine (5) (1 g,0.005 mol) in isopropyl alcohol (25 ml), 4,6-dichloro-1H-pyrazolo[3,4-d]pyrimidine (4) (0.99 g, 0.005 mol) was added and stirred at room temperature for 24 h. After washing the crude solid withisopropyl alcohol, dried to obtain pure [4-(1H-benzimidazol-2-yl)-phenyl]-(6-chloro-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-amine (6) aswhite solid; yield: 79%; mp: >300 C; 1H NMR (400 MHz, CDCl3 + DMSO-d6): delta = 9.75 (s, 1H, ArH), 8.13-8.08 (m, 2H, ArH), 7.92 (d, 1H, J = 8.60 Hz, ArH), 7.72 (d, 1H, J = 8.28 Hz, ArH), 7.62 (bs,1H, NH), 7.15-7.13 (m, 2H, ArH), 6.66 (d, 2H, J = 8.72 Hz, ArH), 5.02(s, 1H, NH); 13C NMR (100 MHz, CDCl3 + DMSO-d6): delta = 147.6, 142.5, 132.2, 130.2, 129.3, 129.2, 124.0, 120.8 (ArC); MS (ESI), m/z: 362.7(M++1); Anal. Calcd for C18H12ClN7: C, 59.76; H, 3.34; N, 27.10, Found: C, 59.83; H, 3.32; N, 27.14.

According to the analysis of related databases, 42754-96-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Singla, Prinka; Luxami, Vijay; Singh, Raja; Tandon, Vibha; Paul, Kamaldeep; European Journal of Medicinal Chemistry; vol. 126; (2017); p. 24 – 35;,
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Reference of 3740-92-9, 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.3740-92-9, name is 4,6-Dichloro-2-phenylpyrimidine, molecular formula is C10H6Cl2N2, molecular weight is 225.07, as common compound, the synthetic route is as follows.

A mixture of 80 (0.25g, 1.11mmol) and IPA (3ml) was stirred for a while and then 2M methylamine in THF (1.39ml, 2.78mmol) was added thereto at 0 °C. The resulting mixture was back to room temperature under stirring for overnight. The reaction was quenched by water and then the mixture was extracted by ethyl acetate (30ml x 3). The residue was purified by flash column over silica gel (ethyl acetate: n-Hexane = 1 :4, Rf = 0.18) to afford 84 (0.22g, 90.23percent) as a pale yellow solid. 1H-NMR (300MHz, CDCl3): delta 3.02 (d, J= 4.2 Hz, 3H), 5.09 (br, 1H), 6.26 (s, 1H), 7.42-7.46 (m, 3H), 8.35-8.37 (m, 2H).

The chemical industry reduces the impact on the environment during synthesis 3740-92-9, I believe this compound will play a more active role in future production and life.

Reference:
Patent; TAIPEI MEDICAL UNIVERSITY; YEN, Yun; LIOU, Jing-Ping; CHEN, Chun-Han; (70 pag.)WO2017/15400; (2017); A1;,
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In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 56181-39-6, name is 5-Bromo-4-chloropyrimidine, the common compound, a new synthetic route is introduced below. Safety of 5-Bromo-4-chloropyrimidine

Step 4: 5-Bromo-4-hydrazinylpyrimidine[0363] A 100-mL round-bottomed flask was charged with a solution of 5- bromo-4-chloropyrimidine (8 g, 25.00 mmol, 1.00 equiv, 60%) in ethanol (50 mL). To this solution was added hydrazine (10 mL, 99%) drop wise with stirring. The resulting solution was stirred overnight at room temperature. The reaction progress was monitored by TLC (MeOH: DCM = 1: 10). The solids were collected by filtration affording 5-bromo-4-hydrazinylpyrimidine as yellow solid (0.83 g, 18%).

The synthetic route of 56181-39-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KALYPSYS, INC.; KAHRAMAN, Mehmet; SMITH, Nicholas, D.; BONNEFOUS, Celine; NOBLE, Stewart, A.; PAYNE, Joseph, E.; WO2010/88518; (2010); A2;,
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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. 29274-22-4, name is Pyrazolo[1,5-a]pyrimidin-5-ol, molecular formula is C6H5N3O, 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. Application In Synthesis of Pyrazolo[1,5-a]pyrimidin-5-ol

A solution of 4H-pyrazolo[1,5-a]pyrimidin-5-one (1 g, 7.40 mmol, 1 .00 equiv) in phosphorus oxychloride ( 1 5 mL) was stirred under nitrogen for 2 h at 1 20 C. The reaction mixture was cooled to rt then concentrated under vacuum. The residue was purified on a si lica gel column eluted with ethyl acetate/petroleum ether ( 1 :2) to give 0.6 g (53%) of the title compound as a light yellow solid. LC/MS (Method I, ESI): RT = 1.21 min, m z = 154.0 [Mu+Eta]

With the rapid development of chemical substances, we look forward to future research findings about 29274-22-4.

Reference:
Patent; GENENTECH, INC.; FORMA TM, LLC; BAIR, Kenneth W.; BAUMEISTER, Timm R.; BUCKMELTER, Alexandre J.; CLODFELTER, Karl H.; DRAGOVICH, Peter; GOSSELIN, Francis; GUNZNER-TOSTE, Janet; HAN, Bingsong; LIN, Jian; LIU, Xiongcai; REYNOLDS, Dominic J.; SMITH, Chase C.; WANG, Zhongguo; ZAK, Mark; ZHANG, Yamin; ZHAO, Guiling; ZHENG, Xiaozhang; YUEN, Po-Wai; WO2013/127266; (2013); A1;,
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Synthetic Route of 932-52-5, 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. 932-52-5, name is 5-Aminopyrimidine-2,4(1H,3H)-dione, molecular formula is C4H5N3O2, 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-dioxo-6-methylpyrido[3,2-d]pyrimidine (FIG. 17a) About 20 g of 5-aminouracil, 80 ml of 20% HCl and 4 ml of crotonaldehyde were heated together under reflux for 1 hour. The solution was evaporated to dryness under rotary evaporation. Water was added to the residue so as to make the mixture just stirrable and then it was triturated with ammonium hydroxide with strong stirring until the pH increased to 10-11. Stirring was continued for another 10 minutes. The precipitate was filtered and was washed with minimal methanol and then chloroform and dried to yield about 17.58 g of the compound of FIG. 17a.

According to the analysis of related databases, 932-52-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Duquesne University of the Holy Ghost; US5958930; (1999); A;; ; Patent; Duquesne University of the Holy Ghost; US5877178; (1999); A;,
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Application of 24415-66-5 , The common heterocyclic compound, 24415-66-5, name is 7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine, molecular formula is C6H5ClN4, 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.

The preparation method of the compound e12 comprises the steps of: taking about 1 mmol of 7-chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine and about 3 mmol.1-(4-bromobenzyl)-1H-indole was added to a 10 mL microwave reaction tube.Further, 2 mL of hexafluoroisopropanol solvent and about 0.1 mmol of bistrifluoromethanesulfonimide catalyst were added, sealed and heated to 100 C with stirring and reacted for about 6 h.Then, the reaction system was monitored by TLC, and after the reaction system was cooled to room temperature, it was separated and purified by column chromatography to obtain pure compound e12.The compound e12 is a yellow solid with a yield of 85%.

The synthetic route of 24415-66-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhengzhou University; Liu Hongmin; Yu Bin; Zheng Yichao; Yuan Shuo; Shen Dandan; (27 pag.)CN109020976; (2018); A;,
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Synthetic Route of 89793-12-4 ,Some common heterocyclic compound, 89793-12-4, molecular formula is C7H7ClN2O2, 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.

10399] A mixture of aniline (3.7 g, 40 mmol), compound 1(7.5 g, 40 mmol), and K2C03 (11 g, 80 mmol) in DMF (100 ml) was degassed and stirred at 120 C. under N2 overnight. The reaction mixture was cooled to r.t. and diluted with EtOAc (200 ml), then washed with saturated brine (200 mlx3). The organic layers were separated and dried over Na2504, evaporated to dryness and purified by silica gel chromatography (petroleum ethersEtOAc=1 0/1) to give the desired product as a white solid (6.2 g, 64%).

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. 89793-12-4, Ethyl 2-chloropyrimidine-5-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Acetylon Pharmaceuticals, Inc.; Jones, Simon Stewart; Yang, Min; Tamang, David Lee; US2015/105384; (2015); A1;,
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Reference of 5305-45-3, 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. 5305-45-3, name is 4,6-Dichloropyrimidine-5-carbonitrile, molecular formula is C5HCl2N3, 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 solution OF 4, 6-DICHLORO-PYRIMIDINE-5-CARBONITRILE (254 mg, 1.47 mmol) and 2,5- difluoroaniline (190 mg, 1.47 mmol) in DMF (3 RNL) at 0C was added K2C03 (203 mg, 1.47 MMOL). The completion of the reaction was monitored by TLC (EtOAc: Hex =1 : 1, Rf= 0.90). After the reaction was complete, 4- (3-ISOPROPYL- [1, 2,4] oxadiazol-5-yl) -piperidine (340 mg, 1.47 mmol) and K2CO3 (406 mg, 2.94 mmol) were added at 0C. The reaction was warmed to rt and stirred for 30 min. The reaction was heated to 40C and maintained for 1 h. The reaction was cooled to rt, poured in to H20 (50 ML) and extracted with EtOAc (50 ML, two times). The EtOAc was dried over MgSO2 and concentrated under vacuum. The crude product was purified over SI02 (EtOAc: Hex = 1 : 1, Rf = 0.44) to afford the desired Compound B131 (465 mg; 71. 1 %). 1H-NMR (DMSO-D6) : 9.32 (1H, s), 8.19 (1H, s), 7. 40-7. 08 (3H, m), 4.54 (2H, m), 3. 48-3. 32 (4H, m), 3. 07-3. 01 (2H, m), 2. 18-2. 14 (2H, b), 1. 96-1. 86 (2H, m), 1.27 (6H, d) ppm. LCMS: 426.43.

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 5305-45-3, 4,6-Dichloropyrimidine-5-carbonitrile.

Reference:
Patent; ARENA PHARMACEUTICALS INC.; WO2004/65380; (2004); A1;,
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