Category: pyrimidines

Electric Literature of 58347-49-2, 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 58347-49-2 as follows.

EXAMPLE 242-rDimethylaminoVl-(4-{7-fluoro-8-methyl-3-r(lS)-l-rpyrazolori.5-alpha1pyrimidin-7- ylamino)ethyl1quinolin-2-vUpiperazin- 1 -vDethanone Intermediate 15 (700 mg, 2.06 mmol), 2-(dimethylamino)-l-(piperazin-l-yl)- ethanone (500 mg), ?-BuOH (10 mL) and DIPEA (2 mL) were combined in a sealed tube and heated to 13O0C for 13 days. The reaction mixture was cooled, concentrated onto silica and purified by column chromatography (SiO2, 0-10% MeOH in EtOAc) to give a white solid. This material, MeOH (8 mL) and 2N HCl in Et2O (4 mL) were combined and stirred at r.t. for 2 days. The reaction mixture was concentrated to give a yellow foam. A portion of this material (50 mg, 0.12 mmol), n-BuOH (6 mL), DIPEA (1 mL) and 7-chloropyrazolo[l,5-alpha]pyrimidine (50 mg, 0.25 mmol) were combined in a sealed tube and heated to 13O0C for 16 h. The reaction mixture was then concentrated to dryness and purified by preparative HPLC to give the title compound (28 mg, 48%) as a tan glass. deltaH (DMSO-Ci6) 8.64 (IH, s), 8.41 (IH, d, J7.80 Hz), 8.13 (2H, m), 7.74 (IH, dd, J8.95, 6.28 Hz), 7.33 (IH, t, J9.13 Hz), 6.44 (IH, d, J2.27 Hz), 6.28 (IH, d, J5.30 Hz), 5.21- 5.13 (IH, m), 4.16-3.73 (4H, m), 3.42-3.17 (6H, m), 2.56 (3H, s), 2.25 (6H, s), 1.89 (3H, d, J 6.71 Hz). LCMS (ES+) 491 (M+H)+, RT 3.23 minutes {Method 1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,58347-49-2, its application will become more common.

Reference:
Patent; UCB PHARMA S.A.; ALLEN, Daniel, Rees; BROWN, Julien, Alistair; BUeRLI, Roland; HAUGHAN, Alan, Findlay; LANGHAM, Barry, John; MATTEUCCI, Mizio; OWENS, Andrew, Pate; RAPHY, Gilles; SHARPE, Andrew; WO2010/133836; (2010); 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.33097-13-1, name is 4,6-Dichloro-2-(methylthio)pyrimidine-5-carbonitrile, molecular formula is C6H3Cl2N3S, molecular weight is 220.08, as common compound, the synthetic route is as follows.Safety of 4,6-Dichloro-2-(methylthio)pyrimidine-5-carbonitrile

Example 43 Synthesis of 5-(4-(2-cyano-3-cyclopropylacrylamido)benzylamino)-7-(3,5-dimethoxyphenylamino)-imidazo[1,2-c]pyrimidine-8-carboxamide Step 1. To a solution of 4,6-dichloro-2-(methylthio)pyrimidine-5-carbonitrile (14 g, 63.6 mmol, 1.0 eq) and 3,5-dimethoxyaniline (9.94 g, 63.6 mmol, 1.0 eq) in THF (300 mL) at 0 C., was added DIEA (12.32 g, 95.4 mmol, 1.5 eq). The resulted mixture was stirred at RT for 4 h. The reaction mixture was diluted with water (30 mL), filtered and dried to give 4-chloro-6-(3,5-dimethoxy-phenylamino)-2-methylsulfanyl-pyrimidine-5-carbonitrile (19 g, 89% in yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,33097-13-1, 4,6-Dichloro-2-(methylthio)pyrimidine-5-carbonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Taunton, JR., John William; Brameld, Kenneth Albert; Goldstein, David Michael; Mcfarland, Jesse; Krishnan, Shyam; Choy, Jonathan; US2014/323464; (2014); A1;,
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Pyrimidine – Wikipedia

Electric Literature of 51940-64-8, 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.51940-64-8, name is Ethyl 2,4-Dichloro-5-pyrimidinecarboxylate, molecular formula is C7H6Cl2N2O2, molecular weight is 221.0407, as common compound, the synthetic route is as follows.

Potassium carbonate (62.50 g, 452.41 mmol) was added to ethyl 2,4-dichloropyrimidine-5-carboxylate (40.00 g, 180.97 mmol) and tetrahydro-2H-pyran-4-amine hydrochloride (24.90 g,10 181.0 mmol) in acetonitrile (1 L). The reaction mixture was stirred at rt for 16 h. The resultingprecipitate was collected by filtration, washed with THF (750 mL) and the combined organic layerswere concentrated in vacuo. The crude product was purified by fcc, elution gradient 0 to 2% THFin DCM, to afford the title compound (37.74 g, 73%) as a pale yellow solid; 1H NMR (400 MHz,DMSO) 1.32 (3H, t), 1.54-1.63 (2H, m), 1.85-1.89 (2H, m), 3.43-3.49 (2H, m), 3.83-3.88 (2H, m),15 4.12-4.26 (lH, m), 4.29-4.34 (2H, m), 8.34 (lH, d), 8.64 (lH, s); m/z MH+ 286.

The chemical industry reduces the impact on the environment during synthesis 51940-64-8, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ASTRAZENECA AB; CANCER RESEARCH TECHNOLOGY LIMITED; FINLAY, Maurice, Raymond, Verschoyle; GOLDBERG, Frederick, Woolf; HOWARD, Martin, Richard; TING, Attilla, Kuan, Tsuei; (145 pag.)WO2019/238929; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 67831-83-8 ,Some common heterocyclic compound, 67831-83-8, molecular formula is C7H7N3OS, 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 (35m) (1.0 g, 5.5 mmol) in POCI3 (10 mL) cooled at 5C on an ice bath was added dropwise diethylaniline (1.0 mL, 6.2 mmol). After 2 hours stirring at 80C, the mixture was poured on crushed ice and the resulting precipitate was filtered off and purified by silica gel column chromatography.Yield: 33%.Melting point: 206-208C.H NMR (DMSO -d6) d 2.56 (s, 3H, S CH3), 6.52 (s, 1H, 5 -H), 7.52 (s, 1H, 6 -H), 12.39 (s, 1H, N H). 13C NM R (DMSO -d6) d 13.8 (SCH3), 99.0 (C-5), 113.2 (C-4a), 126.9 (C-6), 150.4-152.7 (C-4/C-7a),162.7 (C-2).

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. 67831-83-8, 2-(Methylthio)-7H-pyrrolo[2,3-d]pyrimidin-4-ol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; UNIVERSITE DE LIEGE; LANCELLOTTI, Patrizio; OURY, Cecile; PIROTTE, Bernard; (140 pag.)WO2019/158655; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 51674-77-2 ,Some common heterocyclic compound, 51674-77-2, molecular formula is C7H4ClN3, 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.

A mixture of 5-{3-[(1S)-1-aminoethyl]-5-chloro-2-methoxy-6-methylphenyl}-N,N-dimethylpyridine-2-carboxamide dihydrochloride (17 mg, 0.040 mmol), 4-chloropyrido[3,2-d]pyrimidine (6.7 mg, 0.040 mmol) and N,N-diisopropylethylamine (35 muL, 0.20 mmol) in 1-butanol (0.4 mL) was heated at 120 C. for 2 h. The mixture was purified on prep-LCMS (Sunfire Prep C18 5 mum 30¡Á10 mm column, flow rate 60 mL/min, eluting with a gradient of acetonitrile and water with 0.05% TFA) to afford the title product (2.7 mg, 14%). LCMS calculated for C25H26ClN6O2 (M+H)+: m/z=477.2. found: 477.2.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,51674-77-2, its application will become more common.

Reference:
Patent; INCYTE CORPORATION; Li, Yun-Long; Combs, Andrew P.; US2015/361094; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 49845-33-2, 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. 49845-33-2, name is 2,4-Dichloro-5-nitropyrimidine, molecular formula is C4HCl2N3O2, 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 2,4-dichloro-5-nitropyrimidine (500 mg, 2.5 mmol) dissolved in tetrahydrofuran (10 mL), sodium hydroxide (238 mg, 2.8 mmol) and aqueous ammonia (0.3 mL) was added, and reacted for 2 hrs at 55C. The solvent was removed under reduced pressure, and the residue was separated by flash column chromatography (dichloromethane: methanol=100:1), to obtain Compound w: 2-chloro-5-nitro-4-aminopyrimidine as a white solid (0.47 g, yield 84%). MS(ESI)m/z: [M+H]+=175.

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 49845-33-2, 2,4-Dichloro-5-nitropyrimidine.

Reference:
Patent; Shanghai Huilun Life Science & Technology Co., Ltd; FAN, Xing; QIN, Jihong; (43 pag.)EP3284743; (2018); 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. 4595-61-3, name is Pyrimidine-5-carboxylic acid. A new synthetic method of this compound is introduced below., Formula: C5H4N2O2

Example 2 1,4,5,6-Tetrahydropyrimidine-5-carboxylic Acid Hydrochloride Pyrimidine-5-carboxylic acid (5.0 g, 40 mmol) was suspended in a mixture of 150 ml water and concentrated hydrochloric acid (4.0 g, 40.5 mmol). The mixture was hydrogenated at 26 psig over 1.0 g Pd-on-carbon 10percent in a Parr hydrogenator for 3 h. The suspension was filtered and the filter rinsed twice with hot water (20 ml). The filtrate was evaporated in vacuo to give 6.11 g yellow oil (92percent). The oil was crystallized from anhydrous methanol/tetrahydrofuran (THF) to give 5.77 g (87percent) white crystals in two crops. 300 MHz nmr indicated product.

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, 4595-61-3, Pyrimidine-5-carboxylic acid.

Reference:
Patent; The University of Toledo; US5175166; (1992); A;,
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. 38696-20-7, name is 5-Bromo-2-phenylpyrimidine, molecular formula is C10H7BrN2, 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. Recommanded Product: 5-Bromo-2-phenylpyrimidine

Subsequently, 0.96 g of 5-bromo-2-phenylpyrimidine obtained in the above step 1, 1.21 g of 2,6-dimethylphenylboronic acid, 0.87 g of sodium carbonate, 0.76 g of bis (triphenylphosphine) palladium (II) dichloride (Abbreviation: Pd (PPh 3) 2 Cl 2), 15 mL of water and 15 mL of acetonitrile were placed in a recovery flask equipped with a reflux tube and argon bubbling was carried out for 15 minutes. The reaction vessel was heated by irradiating microwave (2.45 GHz 100 W) for 3 hours. Here, 1.21 g of 2,6-dimethylphenylboronic acid, 0.87 g of sodium carbonate and 0.035 g of Pd (PP 3) 2 Cl 2 were placed in a flask and argon bubbling was carried out for 15 minutes. This reaction vessel was heated again by irradiating microwave (2.45 GHz 100 W) for 3 hours. Thereafter, the obtained mixture was suction filtered with water. The obtained solid was purified by flash column chromatography using toluene as a developing solvent to obtain the desired pyrimidine derivative Hppm 2-dmp (white powder, yield 64percent).

With the rapid development of chemical substances, we look forward to future research findings about 38696-20-7.

Reference:
Patent; SEMICONDUCTOR ENERGY LABORATORY COMPANY LIMITED; INOUE, HIDEKO; HARA, TOMOKA; SEO, SATOSHI; SASAKI, TOSHIKI; SUZUKI, KUNIHIKO; (60 pag.)JP2016/6041; (2016); A;,
Pyrimidine | C4H4N2 – PubChem,
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Application of 4786-52-1 ,Some common heterocyclic compound, 4786-52-1, molecular formula is C7H8N2O3, 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.

Ethyl 4-hydroxypy?miotadiotane-5-carboxylate (380 mg, 2.26 mmol) was dissolved in THF (5 mL) and treated with thionyl chloride (1.65 ml, 22.6 mmol). The solution was heated to reflux for 4 h and then concentrated in vacuo, yielding 417 mg (99%) of the crude product This material was used without purification or characterization

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4786-52-1, its application will become more common.

Reference:
Patent; BAYER PHARMACEUTICALS CORPORATION; WO2006/49681; (2006); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 3438-46-8 ,Some common heterocyclic compound, 3438-46-8, molecular formula is C5H6N2, 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.

3-Methyl-pyrimidine [(9. 41] g, 100 mmol), potassium permanganate (26.9 g) and sodium carbonate (10.6 g) was refluxed in water (100 ml) for 72 h followed by filtration through celite. The filtrate was washed with several portions of DCM and EtOAc before acidification with conc. HC1. The formed precipitate was collected and washed with water to yield 1.37 g of the title compound as a white solid. 1H NMR (DMSO-d6) d (ppm): 13.94 (br. s, 1H), 9.37 (d, 1H), 9.07 (d, 1H), 8.01 (dd, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3438-46-8, its application will become more common.

Reference:
Patent; ASTRA ZENECA AB; NPS PHARMACEUTICALS, INC.; WO2004/14881; (2004); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia