Category: pyrimidines

Electric Literature of 1801-06-5 ,Some common heterocyclic compound, 1801-06-5, molecular formula is C5H4ClFN2O, 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.

EXAMPLE AA1 : 5-(r(2S.5f?)-4-ethyl-2.5-dimethylpiperazin-1-vncarbonyl)-lambda/-(5-fluoro-2- methoxypyrimidin-4-yl)-6,6-dimethyl-1 ,4,5.6-tetrahvdropyrrolof3.4-clpyrazol-3-amine; A solution of 5-{[(2S,5f?)-4-ethyl-2,5-dimethylpiperazin-1-yl]carbonyl}-6,6-dimethyl- 1 ,4,5,6-tetrahydropyrrolo[3,4-c]pyrazol-3-amine (289 mg, 0.9 mmol) and 4-chloro-5- fluoro-2-methoxypyrimidine (257 mg, 2 eq) in 5 ml_ of 50percent acetic acid in water was heated in a microwave for 30 min at 8O0C. Purification as described in Example AJ. afforded the title compound AA1 as a white powder (13.1 mg, 3percent). See Table 1 below for NMR data.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1801-06-5, its application will become more common.

Reference:
Patent; PFIZER INC.; WO2008/96260; (2008); A1;,
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Pyrimidine – Wikipedia

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. 313339-35-4, name is 4,6-Dichloro-2-(methylthio)pyrimidine-5-carboxylic acid, the common compound, a new synthetic route is introduced below. Recommanded Product: 313339-35-4

To a mixture of 4,6-dichloro-2-(methylsulfanyl)pyrimidine-5-carboxylic acid (1.50 g) and dichloromethane (15 mL), oxalyl chloride (1.20 mL) and DMF (0.015 mL) were added under ice cooling and stirred 30 minutes under ice cooling and 2 hours at room temperature. The solvent was distilled off under reduced pressure, followed by an azeotropic process with toluene. The resulting residue was dissolved in THF, followed by dropwise addition of 40% aqueous methylamine at -10 C. After the dropwise addition was completed, the reaction liquid was concentrated, and water was added. The resulting solid was collected by filtration and washed with water to give a white solid. The solid was dissolved in ethyl acetate, washed with saturated aqueous sodium chloride, and then dried over anhydrous magnesium sulfate. The solvent was distilled off. To a mixture of the resulting residue and dioxane (20 mL), 3-(methylsulfonyl)aniline hydrochloride (432 mg) and N,N-diisopropylethylamine (0.73 mL) were added and stirred at 100 C. for 4 hours. After cooling, the reaction liquid was diluted with ethyl acetate and washed with saturated aqueous sodium chloride. After drying over anhydrous magnesium sulfate, the solvent was distilled off, and the residue was purified by silica gel column chromatography (eluent; chloroform_methanol=100:0 to 30:1) to give 4-chloro-N-methyl-2-(methylsulfanyl)-6-{[3-(methylsulfonyl)phenyl]amino}pyrimidine-5-carboxamide (445 mg) as a white solid

The synthetic route of 313339-35-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Waters Technologies Corporation; US2012/40968; (2012); A1;,
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Application of 42839-08-7, Adding some certain compound to certain chemical reactions, such as: 42839-08-7, name is Ethyl pyrimidine-2-carboxylate,molecular formula is C7H8N2O2, 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 42839-08-7.

General procedure: To the solution of ester (10 mmol) in THF (20 mL) and ethyl acetate (70 mmol), LiHMDS (30 mmol) was added very quickly at -40 C, and stirred at this temperature for 20 min. After completion of the reaction, reaction mixture was quenched with acetic acid (50 mmol) and then basified using 10% NaHCO3 solution, extracted with ethyl acetate (2×100 mL), the combined organic layer was washed with water and brine solution and dried over Na2SO4. The specific purification procedure for each compound has been included along with their characterization data.

According to the analysis of related databases, 42839-08-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Venkat Ragavan; Vijayakumar; Rajesh; Palakshi Reddy; Karthikeyan; Suchetha Kumari; Bioorganic and Medicinal Chemistry Letters; vol. 22; 12; (2012); p. 4193 – 4197;,
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Related Products of 4319-87-3, 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.4319-87-3, name is 5-Bromo-4-methoxy-6-methylpyrimidine, molecular formula is C6H7BrN2O, molecular weight is 203.04, as common compound, the synthetic route is as follows.

A mixture of 4-[3-methyl-4-(4,4,5,5-tetram ethyl-i ,3,2-d ioxaborolan-2-yl)phenoxy]furo[3,2- c]pyridine (C2) (4.0 g, ii mmol), 5-bromo-4-methoxy-6-methylpyrimidine (Z. Wang et al., Synthesis2Oll, 1529-1531)(2.Og, 10 mmol), [1,1?-bis(diphenylphosphino)ferrocene]dichloropalladium(ll) (1.1 g, 1.4 mmol) and potassium carbonate (4.0 g, 29 mmol) in 1 ,4-dioxane (30 mL) containing 5 drops of water was heated at 120 00 for 2 hours. After filtration and concentration of the filtrate under reduced pressure, the residue was purified by silica gel chromatography (Eluent: 33% ethyl acetate in petroleum ether) to give the product as a yellow solid. Yield: 1.8 g, 5.2 mmol, 52%. 1H NMR (400 MHz, ODd3) oe8.72 (s, 1H), 8.07 (d, J=6.0 Hz, 1H), 7.66 (d, J=2.3 Hz, 1H), 7.25 (dd, J=5.9, 0.9 Hz, 1H), 7.19-7.21 (m, 1H), 7.09-7.16 (m, 2H), 6.88 (dd, J=2.3, 0.8 Hz, 1H), 3.95 (s, 3H), 2.29 (s, 3H), 2.07 (s,3H).

Statistics shows that 4319-87-3 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-4-methoxy-6-methylpyrimidine.

Reference:
Patent; PFIZER INC.; COE, Jotham, Wadsworth; ALLEN, John, Arthur; DAVOREN, Jennifer, Elizabeth; DOUNAY, Amy, Beth; EFREMOV, Ivan, Viktorovich; GRAY, David, Lawrence, Firman; GUILMETTE, Edward, Raymond; HARRIS, Anthony, Richard; HELAL, Christopher, John; HENDERSON, Jaclyn, Louise; MENTE, Scot, Richard; NASON, Deane, Milford, II; O’NEIL, Steven, Victor; SUBRAMANYAM, Chakrapani; XU, Wenjian; WO2014/72881; (2014); A1;,
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Reference of 186519-92-6, Adding some certain compound to certain chemical reactions, such as: 186519-92-6, name is 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylic acid,molecular formula is C7H4ClN3O2, 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 186519-92-6.

To a stirred suspension of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylic acid (G-l) (3.11 g,15.7 mmol, 1.0 eq) and a catalytic amount of DMF in a mixture of DCM (40 mL) and THF (40 mL) at RT, oxalyl dichloride (2.0 mL, 23.5 mmol, 1.5 eq) is added dropwise. The resulting mixture is stirred for 2 h and then concentrated in vacuo. The residue (G2) is dissolved in DCM (50 mL) and the resulting solution is added dropwise to saturated aqueous ammonium hydroxide (200 mL) at RT. The resulting mixture is stirred for 30 min and then filtered. The filter cake is then rinsed with H20 (30 mL X 2). The filtrate is acidified with con. HC1 to adjust the pH to 4-5. The solid is collected by filtration, rinsed with water and dried in vacuo to afford the product, 4-chloro-7H-pyrrolo[2,3-d]pyrimidine- 5-carboxamide (G-3).

According to the analysis of related databases, 186519-92-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; INTELLIKINE, INC.; INFINITY PHARMACEUTICALS, INC.; REN, Pingda; LIU, Yi; LI, Liansheng; CHAN, Katrina; CASTRO, Alfredo, C.; EVANS, Catherine, A.; WO2011/146882; (2011); A1;,
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Synthetic Route of 216309-28-3 , The common heterocyclic compound, 216309-28-3, name is 5-((Trimethylsilyl)ethynyl)pyrimidine, molecular formula is C9H12N2Si, 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.

(8S,9S)-9-epi-Azido-9-dehydroxy quinine (1.045 g, 3.0 mmol)was dissolved in a mixture of tert-butanol and water (12 mL, 1:1,v/v), and 2-(TMS-ethynyl)-pyrimidine (631 mg, 3.58 mmol,1.2 equiv) was added. Then pyridine (0.25 mL, 3.1 mmol,1.0 equiv), CuSO4.5H2O (290 mg, 1.25 mmol 0.4 equiv), sodiumascorbate (494 mg, 2.49 mmol, 0.8 equiv) and K2CO3 (806 mg,5.83 mmol, 1.9 equiv) were added. The suspension was stirred atroom temperature for 3 days. Then saturated aqueous Na2S solutionwas added and the mixture stirred for an additional 0.5 h,while dark brown precipitate formed. The mixture was filteredthrough Celite and washed with CH2Cl2. The filtrate was washedwith water, dried over Na2SO4 and evaporated. Chromatographyon silica gel (CHCl3/MeOH, 10:1 v/v.) gave white crystalline solid(1.233 g, 91%). M.p.: 248.53-250.7 C, [a]D21 = -182 (c 0.91, CH2Cl2).1H NMR (600 MHz, CDCl3) delta 8.81 (d, J = 4.4 Hz, 1H), 8.69 (d,J = 4.7 Hz, 2H), 8.15 (s, 1H), 7.99 (d, J = 9.1 Hz, 1H), 7.603-7.57(m, 1H), 7.50 (d, J = 4.7 Hz, 1H), 7.34 (dd, J = 9.1, 2.2 Hz, 1H), 7.11(t, J = 4.9 Hz, 1H), 6.51 (d, J = 11.3 Hz, 1H), 5.91 (ddd, J = 17.5,10.7, 6.9 Hz, 1H), 5.08 (d, J = 9.4 Hz, 1H), 5.06 (d, J = 18.2 Hz, 1H),3.94 (s, 3H), 3.933-3.88 (m, 1H), 3.493-3.42 (m, 1H), 3.14 (dd,J = 14.0, 10.1 Hz, 1H), 2.74 (dd, J = 14.3, 4.1 Hz, 1H), 2.713-2.65(m, 1H), 2.343-2.27 (m, 1H), 1.96 (t, J = 11.9 Hz, 1H), 1.793-1.76(m, 1H), 1.653-1.54 (m, 2H), 0.94 (dd, J = 14.1, 7.1 Hz, 1H)(Fig. S8a, SI).13C NMR (151 MHz, CDCl3) delta 159.1, 158.8, 157.4, 147.3, 147.2,145.1, 141.4, 138.8, 132.0, 128.2, 123.4, 122.6, 119.5, 119.2,114.8, 100.8, 61.0, 58.0, 56.1, 55.9, 41.1, 39.1, 27.74, 27.72, 27.70(Fig. S8a, SI).HRMS (ESI) Calc. for [C26H27N7O+H]+: 454.2350, found:454.2353 (Fig. S5, SI).

The synthetic route of 216309-28-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ga??zowska; Boraty?ski; Kowalczyk; Lipke; Czapor-Irzabek; Polyhedron; vol. 121; (2017); p. 1 – 8;,
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Pyrimidine – Wikipedia

Reference of 38275-43-3, 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. 38275-43-3, name is 2-(Methylthio)pyrimidine-5-carbonitrile, molecular formula is C6H5N3S, 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 mixture of 2-(methylsulfanyl)pyrimidine-5-carbonitrile (25.00 g, 165.35 mmol, 1.00 eq) and hydroxylamine hydrochloride (22.98 g, 330.70 mmol, 2.00 eq) in ethanol (250.00 ml) and water (250.00 ml) was added sodium hydrogen carbonate (27.78 g, 330.70 mmol, 2.00 eq). The reaction was stirred at 70 C for 16 h. This mixture was filtered and washed with water (50 ml*4). The residue was collected and evaporated. This residue N’-hydroxy-2-(methylsulfanyl)pyrimidine-5- carboximidamide (29.00 g, crude) was used for next step without further purification

According to the analysis of related databases, 38275-43-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER AKTIENGESELLSCHAFT; BAYER CROPSCIENCE AKTIENGESELLSCHAFT; BRUNET, Stephane; GOeRTZ, Andreas; GOURGUES, Mathieu; HILT, Emmanuelle; JAKOBI, Harald; NAUD, Sebastien; REBSTOCK, Anne-Sophie; DUCERF, Sophie; (78 pag.)WO2019/122323; (2019); A1;,
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Pyrimidine – Wikipedia

Electric Literature of 69205-79-4, 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 69205-79-4 as follows.

Anew synthesis of 7-formyl-preQ0 (systematic name, 2-amino-5-formylpyrrolo[2,3-d]pyrimidin-4-one) that, contrary to literature-known procedures (21-23), does not require protecting group chemistry was developed. PreQ0 (808 mg, 4.61 mmol)and sodium hypophosphite dihydrate (1.44 g, 13.6 mmol) were dissolved in the solvent mixture (15 ml of pyridine/acetic acid/deionized water in a ratio of 2:1:1) and stirred under inert atmosphere.Raney nickel catalyst (slurry in water, 500 mg) wasadded to the stirred reaction mixture. Safety precaution: dryRaney nickel is pyrophoric and should always be handled underinert atmosphere. The resulting reaction mixture was heated to50 C for 5 h. Subsequently, the reaction mixture was cooled to room temperature and filtered over a pad of celite. The filtrate was reduced in vacuo. The remaining brown residue was dissolvedin 6 M aqueous potassium hydroxide solution. The remaining solids were filtered off. The filtrate was cooled to 0 Cand neutralized by addition of concentrated aqueous HCl. Theproduct precipitated from the solution and was isolated by filtrationand washed with copious amounts of ice water and acetone(brown solid, 770 mg, 94%). 1H NMR (DMSO-d6) 6.35(bs, 2H, NH2), 7.49 (s, 1H, H-8), 10.04 (s, 1H, CHO), 10.72 (bs,1H, H-9), 11.96 (bs, 1H, H-1); 13C NMR (DMSO-d6) 98.36(C-7), 120.34 (C-8), 124.50 (C-5), 153.40 (C-2), 153.83 (C-4),159.02 (C-6), 185.47 (CHO). NMR data were recorded on aBruker AVANCE III with autosampler (1H NMR 300.36 MHz,13C NMR 75.53 MHz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,69205-79-4, its application will become more common.

Reference:
Article; Jung, Jihye; Czabany, Tibor; Wilding, Birgit; Klempier, Norbert; Nidetzky, Bernd; Journal of Biological Chemistry; vol. 291; 49; (2016); p. 25411 – 25426;,
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Pyrimidine – Wikipedia

Synthetic Route of 69696-37-3 , The common heterocyclic compound, 69696-37-3, name is 5-Bromo-2,4-dimethylpyrimidine, molecular formula is C6H7BrN2, 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 tetrahydropyran-4- amine (1.35 g, 13.4 mmol) in toluene (5 ml) was added 5-bromo-2,4- dimethyl-pyrimidine (500 mg, 2.67 mmol), BINAP (333 mg, 0.53 mmol), Cs2C03 (1.74 g, 5.35 mmol) and Pd(OAc)2 (60 mg, 0.27 mmol) at rt under N2. The mixture was heated at 120 C for 3 h under a N2 atmosphere. H20 (10 ml) was added and the mixture was extracted with EtOAc (3 x 10 ml). The combined organic layers were washed with brine (5 ml), dried over Na2S04, filtered and concentrated under reduced pressure to give a residue. The residue was purified by FCC (0 – 50 % MeOH in EtOAc) to give the title compound as a brown solid (Y = (1619) 90 %). H NMR (400 MHz, methanol-^) d ppm 7.98 (s, 1H), 4.02 – 3.99 (m, 2H), 3.62 – 3.54 (m, 3H), 2.51 (s, 3H), 2.39 (s, 3H), 2.05 – 1.92 (m, 2H), 1.66 – 1.56 (m, 2H).

The synthetic route of 69696-37-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NODTHERA LIMITED; HARRISON, David; WATT, Alan Paul; BOCK, Mark G.; (334 pag.)WO2019/121691; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 1801-06-5 ,Some common heterocyclic compound, 1801-06-5, molecular formula is C5H4ClFN2O, 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 100 ml dichloroethane and 25 ml acetonitrile as a solvent. Using dichloroethane as a solvent, the first 100 ml dichloroethane and 25 ml acetonitrile is poured into the 250 ml flask is, by adding 14.4g (0.1mol) of 2-methoxy-5-fluoro-4-hydroxy-pyrimidine. After dropwise 32.2g (0.3mol) of phosphorus oxychloride, within half an hour after the dropping, the stirring 10 minutes later, start dropwise triethylamine 21.2g (0.21mol), heating to 60 °C, stirring 2 hours later, cooling. In the reaction solution is poured into the crushed ice, to be layered. Applying the organic phase is 2-methoxy-4-chloro-5-fluoro pyrimidine dichloroethane solution.Then, 15 g of hydrazine hydrate were added dropwise thereto, and the mixture was heated to 70 ° C and reacted 2h, and the reaction was monitored by HPLC. The product was obtained as white needle crystals. 2-Methoxy-4-hydrazino-5-fluoro pyrimidine 11.98g (0.075 mol), m.p. 187 ° -188 ° C, product content 98.5percent, yield 77percent.

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. 1801-06-5, 4-Chloro-5-fluoro-2-methoxypyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Shenyang Sinochem Pesticide Chemical R & D Co., Ltd; Cao, Wei; Sun, Ke; Guan, Yunfei; Pei, Heying; Li, Yanjuan; (6 pag.)CN105801492; (2016); A;,
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