Pyrimidines

Reference of 98141-42-5, 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. 98141-42-5, name is 4,6-Dichloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidine, molecular formula is C6H4Cl2N4, 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.

General procedure: To a solution of 2,4-dichloropyrrolo[1,2-f][1,2,4]triazine (4a) (0.5 g, 2.7 mmol) in 2-Propanol (6 mL) was added (S)-pyrrolidin-2-ylmethanol (0.39 mL, 4.0 mmol), DIPEA (1.39 mL, 8.0 mmol) and heated at 90 C for 1 hr. The reaction was cooled to room temperature and solid obtained was collected by filtration to afford (S)-(l-(2-chloropyrrolo[2,l-f][l,2,4]triazin-4- yl)pyrrolidin-2-yl)methanol (96a) (0.49 g, 73 % yield) as a white solid; NMR (300 MHz, DMSO-i/e): delta 7.70 (dd, J= 2.6, 1.4 Hz, 1H), 6.97 (dd, J= 4.7, 1.6 Hz, 1H), 6.80 – 6.57 (m, 1H), 5.15 (t, J = 5.7 Hz, 1H, D2O exchangeable), 4.87 (t, J= 5.7 Hz, 1H), 4.44 (d, J= 17.8 Hz, 1H), 4.05 – 3.82 (m, 1H), 3.72 – 3.39 (m, 2H), 2.22 – 1.84 (m, 4H). MS (ES+): 253.3, 255.3 (M+2); MS (ES-): 287.2, 289.2 (M+Cl).

According to the analysis of related databases, 98141-42-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BIOCRYST PHARMACEUTICALS, INC.; KOTIAN, Pravin, L.; BABU, Yarlagadda, S.; KUMAR, V., Satish; ZHANG, Weihe; LU, Peng-Cheng; RAMAN, Krishnan; (747 pag.)WO2018/232094; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 42839-04-3, 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 42839-04-3, name is 4-Cyanopyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

After dissolving 5.0g (47.6 mmol) of 2-cyanopyrimidine in 100 ml of ethanol at room temperature, 20ml (475.7 mmol) of hydrazine hydrate was added thereto and stirred at room temperature for about two days. After completion of the reaction, the reaction product was concentrated under reduced pressure, and then extracted with 100 ml of salt water and 200 ml of dichloromethane to obtain an organic layer, which was then dried using magnesium sulfate and distilled under reduced pressure. The resulting product was separated and purified using column chromatography to obtain 3.0g (21.9 mmol, Yield 46percent) of Intermediate 40(2). LC-MS m/z = 138(M+H)+

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 42839-04-3, 4-Cyanopyrimidine.

Reference:
Patent; Samsung Display Co., Ltd.; Choi, Jong-Won; Park, Bum-Woo; Lee, Sun-Young; Choi, Wha-Il; Kim, So-Yeon; Lee, Ji-Youn; Kwak, Yoon-Hyun; EP2706064; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 6299-25-8, 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. 6299-25-8, name is 4,6-Dichloro-2-(methylthio)pyrimidine, molecular formula is C5H4Cl2N2S, 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.

[00230] Reagents[00231] Experimental procedure:? ; Take ammonia in THF into a 2 L autoclave and add 4, 6-dichloro-2-(Methylthio) pyrimidine slowly.? Heat the reaction mixture to 50-60 C and maintain the reaction at 50-60 C for 3-4 hours (Inbuilt pressure 7- 8 Kg/cm ).? Check the progress of the reaction by TLC. Upon completion, the reaction was brought to 25-35 C.? Concentrate the reaction mixture under vacuum.? Charge Hexane and stir for 30-45 minutes at 25-35 C.? Filter the solid and wash the solid with Hexane.? Wash the solid with water (2X400 mL).? Dry the solid at 25-35 C till M.C reaches to less than 2%.Yield 352.0 g% of Yield: 97.77%.Purity by HPLC: 99.07%.Other suitable conditions such as ammonia in MeOH or dioxane could be used accordingly when different analogs are used. Example 1- 2. Preparation of 4-Amino-6-chloro-2- meth lthio)pyrimidine, 6.1

According to the analysis of related databases, 6299-25-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KINAGEN, INC.; MURPHY, Eric, A.; CHERESH, David, A.; ARNORD, Lee, Daniel; WO2011/97594; (2011); A2;,
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Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 26032-72-4, 2,4-Dichloro-6-phenylpyrimidine, 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: 2,4-Dichloro-6-phenylpyrimidine, blongs to pyrimidines compound. Recommanded Product: 2,4-Dichloro-6-phenylpyrimidine

Step (i): Synthesis of (2-chloro-6-phenyl-pyrimidin-4-yl)-(1-ethyl-pyrrolidin-2ylmethyl)-amine To 2,4-dichloro-6-phenyl-pyrimidine (1.508 g, 6.6 mmol), dissolved in THF (10 mL), was added 2-(aminomethyl)-1-ethylpyrrolidine (0.96 mL, 6.6 mmol). The resulting mixture was cooled to -60 C. and then treated with lithium bis (trimethylsilyl) amide (13.2 mL, 13.2 mmol, 1M). The resulting solution was allowed to stir at -60 C. for 10 min and was quenched with water slowly. The mixture was diluted with ethylacetate, and washed two times with water and one time with brine. The organic phase was dried over sodium sulfate, filtered, and concentrated by rotary evaporation. Purification (Biotage Horizon HPFC chromatography system, SiO2, 95:5 dichloromethane: MeOH) gave the title compound as a solid (1.1 g, 52% yield) in addition to C-2 regioisomer (not fully characterized).HPLC: Betasil ODS-3V C18, [KH2PO4 (0.01M, pH 3.2): CH3CN], gradient, 264 nm, Rt 10.1 & 10.7 min, 52.8, 43.8% purity respectively.1H NMR (300 MHz, CDC13, TMS): delta 7.98-7.94 (m, 2H), 7.48-7.44 (m, 3H), 6.96 (s, 1H), 6.02-5.87 (m, 1H), 3.75 (b s, 1H), 3.39-3.19 (m, 2H), 2.91-2.65 (m, 2H), 2.29-2.12 (m, 2H), 1.97-1.60 (m, 4H), 1.12 (t, J=7.5 Hz, 3H).LC-MSD (ES+): m/z [317 (M+H)+, 100].;

The synthetic route of 26032-72-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dr. Reddy’s Laboratories Ltd.; US2010/144722; (2010); A1;,
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Pyrimidine – Wikipedia

Application of 20737-41-1, Adding some certain compound to certain chemical reactions, such as: 20737-41-1, name is 4-Aminopyrimidine-5-carboxylic acid,molecular formula is C5H5N3O2, 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 20737-41-1.

Example 90; N-Methyl-4-(2-(2-oxoindolin-5-ylamino)-5-(trifluoromethyl)pyridin-4-ylamino)pyrimidine-5-carboxamide; 4-Amino-7V-metb.ylpyrimidine-5-carboxamide; To the mixture of 4-aminopyrimidine-5-carboxylic acid (0.75 g, 5.39 mmol), methylamine hydrogen chloride (0.44 g, 1.2 eq), EDC (1.67 g, 1.5 eq), HOBt (0.87 g, 1.2 eq) in DMF (2OmL) was added DIEA (3.8 mL, 4.0 eq). The mixture was stirred at room temperature overnight. The crude was concentrated and dissolved in EtOAc. It was washed with saturated NaHCO3 solution. The solvent was removed and the crude was purified by silica gel chromatography (0%~20% MeOH/DCM) to obtain the desired product 4-amino-N-methylpyrimidine-5-carboxamide (0.701 g, isolated yield 85%).

According to the analysis of related databases, 20737-41-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THE SCRIPPS RESEARCH INSTITUTE; WO2008/115369; (2008); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 55583-59-0, 2,5-Diamino-4,6-dichloropyrimidine, 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: C4H4Cl2N4, blongs to pyrimidines compound. Formula: C4H4Cl2N4

In a reaction vessel, 4,6-dichloropyrimidine-2,5-diamine (1.00 g, 5.59 mmol),4- (N, N-Dimethylamino) phenylboronic acid(0.922 g, 5.5 9 mmol),Sodium carbonate (2.96 g, 27.9 mmol),To a solution of tetrakis (triphenylphosphine) palladium (0) (0.323 g, 0.560 mmol) in toluene (56 mL) was added ethanol (14 mL) and distilled water (14 mL) at room temperature, and then under an argon atmosphere. After stirring for 20 hours under heating and reflux conditions, the reaction solution was cooled to room temperature. Distilled water (16 mL) was added and stirred, and the separated aqueous layer was extracted three times with ethyl acetate (20 mL).Thereafter, the whole organic layer was combined, saturated aqueous sodium chloride solution (20 mL) was added thereto, the mixture was stirred and washed, anhydrous sodium sulfate was added to the separated organic layer for dehydration, and the filtrate after filtration was concentrated under reduced pressure .The concentrate thus obtained is purified by flash column chromatography (silica gel, n-hexane / ethyl acetate),4-Chloro-6- (4- (dimethylamino) phenyl) pyrimidine-2,5-diamine(0.727 g, 49% yield).

The synthetic route of 55583-59-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Microbial Chemistry Research Foundation; Kumagai, Naoya; Noda, Hidetoshi; Asada, Yasuko; Shibazaki, Masakatsu; (48 pag.)JP2019/64981; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 33097-11-9, 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. 33097-11-9, name is 4,6-Dichloro-2-(methylthio)pyrimidine-5-carbaldehyde, molecular formula is C6H4Cl2N2OS, 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.

General procedure: To a stirred solution of aldehyde 1 (1.0mmol, 1equiv) in 3mL DMF was added enamine 2 (1.15equiv) followed by addition of a few drops of satd ethereal HCl. (0027) Except for 6d: Mixture was stirred at ambient temperature for period of time indicated in Table 1. After removing of solvent (50C/5 Torr) the residue was stirred with water (10mL) for 1h, crystals were filtered and dried at 110C/5 Torr to give compound 6 with purity?94%. Recrystallization from DMF can be used for purification, if necessary. (0028) For 6d: After stirring for 20h the additional portion of enamine 4d (0.15equiv) was added and the mixture was left at ambient temperature for 4 days. After removing of solvent (50C/5 Torr) the residue was dissolved in CHCl3 (30mL), washed with water, satd NaHCO3 and brine. Compound 6d was isolated using column chromatography on silica (EtOAc-nHexane 1:1, Rf?0.25).

According to the analysis of related databases, 33097-11-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Chizhova, Maria E.; Bakulina, Olga Yu.; Ivanov, Alexander Yu.; Lobanov, Pavel S.; Dar’in, Dmitrii V.; Tetrahedron; vol. 71; 36; (2015); p. 6196 – 6203;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 58347-48-1 ,Some common heterocyclic compound, 58347-48-1, molecular formula is C10H10ClN3O2, 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 ethyl 7-chloro-5-methylpyrazolo[l,5-a]pyrimidine-3-carboxylate (1.0 g, 4.18 mmol) in toluene (10 mL) was added (Bu3Sn)20 (5.0 g, 8.36 mmol). The reaction mixture was stirred at 120 C for 2 days, and concentrated in vacuo. The residue was dissolved in EtOAc (10 mL), and basified with sat. aHC03solution (10 mL) to pH~8-9. The aqueous phase was separated and acidified with 6N HC1 (10 mL) to pH~5. The solution was extracted with EtOAc (10 mL x 3). The organic phases were dried over anhydrous Na2S04, and filtered. The filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (PE/EA; 1 : 1) to give 7-chloro-5-methylpyrazolo[l,5-a]pyrimidine-3- carboxylic acid (230 mg, 26%) as a white solid. LC-MS m/z: 211.0 [M+H]+, Purity (214 nm): >97%, tR= 1.23min.

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. 58347-48-1, Ethyl 7-chloro-5-methylpyrazolo[1,5-a]pyrimidine-3-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; LYSOSOMAL THERAPEUTICS INC.; SKERLJ, Renato, T.; LANSBURY, Peter, T.; GOOD, Andrew, C.; BOURQUE, Elyse, Marie Josee; (139 pag.)WO2016/73895; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 18592-13-7, 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 18592-13-7, name is 6-(Chloromethyl)pyrimidine-2,4(1H,3H)-dione. This compound has unique chemical properties. The synthetic route is as follows.

6-Chloromethyl uracil (500 mg, 3.1 mmol) was dissolved in THF (50 mL) and the solution was treated with 4-methoxybenzyl alcohol (860 mg, 6.2 mmol), triphenylphosphine (2.45 g, 9.3 mmol) and diisopropylazodicarboxylate (1.26 g, 6.2 mmol). The reaction was allowed to stir overnight at room temperature. The mixture was then poured over water (75 mL) and was extracted with ethyl acetate (3*50 mL). The combined organic extracts were dried over Na2SO4, filtered and reduced. Compound 28a was isolated and purified by normal phase column chromatograpy (silica gel, 20% EtOAc/heptane-100% EtOAc/heptane). M+ (ES+)=401.1.

According to the analysis of related databases, 18592-13-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Coats, Steven J.; Dyatkin, Alexey B.; He, Wei; Lisko, Joseph; Miskowski, Tamara; Ralbovsky, Janet L.; Schulz, Mark; US2008/269225; (2008); 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.1208170-17-5, name is 4-Chloro-6-methyl-2-(methylthio)pyrimidine-5-carbonitrile, molecular formula is C7H6ClN3S, molecular weight is 199.66, as common compound, the synthetic route is as follows.name: 4-Chloro-6-methyl-2-(methylthio)pyrimidine-5-carbonitrile

General procedure: A mixture of 3a,b (2.86 mmol), 4-methoxyaniline (0.36 g,2.88 mmol) and anhydrous K2CO3 (0.4 g, 5.76 mmol) inEtOH (15 ml) was heated under reflux for 5 h. It was thencooled, filtered and the filtrate was concentrated to half itsvolume. The obtained precipitate was filtered and crystallizedfrom EtOH-H2O (3:1 v/v).4-(4-Methoxyanilino)-6-methyl-2-(methylthio)-pyrimidine-5-carbonitrile (4a) Yield 71%; mp 158-160 C; IR v/cm-1:3300 (NH), 2214 (C?N), 1614 (C=N), 1604 (C=C-Ar),1293, 1134 (vas and vs C-O-C); 1H NMR (CDCl3, 60 MHz)delta/ppm: 7.49 (d, 2H, Ar-Hs, o- to NH-Ar, J = 12.6 Hz), 7.21(s, br, 1H, NH), 6.90 (d, 2H, Ar-Hs, o- to OCH3, J = 12.0Hz), 3.83 (s, 3H, OCH3), 2.58 (s, 3H, S-CH3), 2.50 (s, 3H,CH3); EIMS m/z 286 (M+., 100), 271 (33), 270 (25), 238(13); Anal. Calcd. for C14H14N4OS: (286.35): C, 58.72; H,4.93; N, 19.72. Found: C, 58.97; H, 4.98; N, 19.57.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1208170-17-5, 4-Chloro-6-methyl-2-(methylthio)pyrimidine-5-carbonitrile, and friends who are interested can also refer to it.

Reference:
Article; Farghaly, Ahmed M.; AboulWafa, Omaima M.; Elshaier, Yaseen A. M.; Badawi, Waleed A.; Haridy, Haridy H.; Mubarak, Heba A. E.; Medicinal Chemistry Research; vol. 28; 3; (2019); p. 360 – 379;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia