Pyrimidines

Synthetic Route of 4316-93-2 , The common heterocyclic compound, 4316-93-2, name is 4,6-Dichloro-5-nitropyrimidine, molecular formula is C4HCl2N3O2, 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.

Step 1: A solution of dibenzylamine (10.2 g) in dichloromethane (30 mL) is dripped into a solution of 4,6-dichloro-5-nitropyrimidine (10 g) in dichloromethane (70 mL) on an ice bath. Then triethylamine (14.4 mL) is added, and the mixture is stirred for 1 hour. Water is added to the reaction mixture, the organic layer is washed with a saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate, and the solvent is concentrated under reduced pressure to obtain N,N-dibenzyl-6-chloro-5-nitropyrimidine-4-amine (19.2 g).

The synthetic route of 4316-93-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACERTA PHARMA B.V.; HAMDY, Ahmed; ROTHBAUM, Wayne; IZUMI, Raquel; LANNUTTI, Brian; COVEY, Todd; ULRICH, Roger; JOHNSON, Dave; BARF, Tjeerd; KAPTEIN, Allard; (268 pag.)WO2016/24227; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 3680-69-1, 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 3680-69-1, name is 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 4-chloropyrrolo[2,3-d]pyrimidine (200 g, 1.3 mol, 1.0 eq.) in N,N-dimethylformamide was added 60% NaH (62.4 g, 1.56 mol, 1.2 eq.) in an ice bath, and stirred for 1 hour at room temperature after completion of addition. 2-(Trimethylsilyl)ethoxymethyl chloride (SEMCl, 260 g, 1.56 mol, 1.2 eq.) was slowly added drop-wise under cooling in an ice bath. After completion of addition, the reaction was stirred for 1 hour in an ice bath, quenched with water, and extracted with ethyl acetate. The combined organic phase was washed with a saturated brine solution, dried over anhydrous sodium sulfate, and filtrated. The filtrate was concentrated under reduced pressure to obtain residue, which was purified by column chromatography on silica gel to afford 4-chloro-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine (2) (312.2 g, yield: 91.8%). 1H-NMR (500 MHz, CDCl3): delta 8.64 (s, 1H), 7.38 (d, J=3.6 Hz, 1H), 6.65 (d, J=3.6 Hz, 1H), 5.64 (s, 2H), 3.52 (t, J=8.2 Hz, 2H), 0.90 (t, J=8.2 Hz, 2H), -0.07 (s, 9H); HRMS (ESI) calcd. for C12H18N3OSi [M+H]+ 284.0980; Found: 284.0995.

According to the analysis of related databases, 3680-69-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CHIA TAI TIANQING PHARMACEUTICAL GROUP CO., LTD.; Lianyungang Runzhong Pharmaceutical Co., Ltd.; CENTAURUS BIOPHARMA CO., LTD.; ZHANG, Xiquan; Zhang, Aiming; Zhou, Zhou; Yao, Huadong; Xie, Jie; (32 pag.)US2019/211021; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 3177-24-0 , The common heterocyclic compound, 3177-24-0, name is 2,4-Dichloropyrimidine-5-carbonitrile, molecular formula is C5HCl2N3, 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.

2,4-Dichloropyrimidin-5-carbonitrile (1.00 g, 5.75 mmol) was dissolved in 30 mL DMF. To it were added (R)-2-aminobutanamide hydrochloride (1.20 g, 8.62 mmol) and DIEA (3.0 mL, 17.24 mmol). The mixture was stirred at 50°C for 10 m to afford two coupling product in about equal amount in quantitative yield. The mixture was concentrated in vacuo, diluted with EtOAc, washed with brine twice, dried, concentrated and subjected to flash column to separate (R)-2-((4-chloro-5-cyanopyrimidin-2-yl)amino)butanamide.The mixture of (R)-2-((4-chloro-5-cyanopyrimidin-2-yl)amino)butanamide (400 mg, 1.7 mmol), 3-methylisothiazol-5-amine hydrochloride (770 mg, 5.1 mmol), fine powder Cs2C03 (3.88 g, 11.9 mmol), BINAP (212 mg, 0.34 mmol) and Pd(OAc)2 (77 mg, 0.34 mmol) in 50 mL dioxane was degassed using argon stream and stirred at 105°C under argon atmosphere for 6 h. It was diluted with 400 mL EtOAc, vigorously stirred, filtered through celite, concentrated in vacuo and subjected to flash column to isolate (R)-2-((4-chloro-5-cyanopyrimidin-2- yl)amino)butanamide (210 mg).

The synthetic route of 3177-24-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PORTOLA PHARMACEUTICALS, INC.; JIA, Zhaozhong J.; KANE, Brian; XU, Qing; BAUER, Shawn M.; SONG, Yonghong; PANDEY, Anjali; DICK, Ryan; WO2013/78468; (2013); A1;,
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Pyrimidine – Wikipedia

Application of 20090-69-1, Adding some certain compound to certain chemical reactions, such as: 20090-69-1, name is 2-Chloro-4-methylpyrimidin-5-amine,molecular formula is C5H6ClN3, 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 20090-69-1.

To a stirred solution of 2-chloro-4-methylpyrimidin-5-amine (2 g, 14.706 mmol, CAS RN20090-69-1) in DCM (50 mL) was added acetic anhydride (2.96 mL, 29.412 mmol) followed by triethyl amine (6.15 mL, 44.118 mmol) and reaction mixture was stirred at 25C for 16 h. After completion of the reaction, the mixture was evaporated.. The crude product was purified by chromatography over silica gel (23-26% EtOAc/n-hexane) to afford the compound as an offwhite solid (2.49 g, 91%). MS (ESI): mlz = 186.1 [M+H]+

According to the analysis of related databases, 20090-69-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BUETTELMANN, Bernd; KOCER, Buelent; KUHN, Bernd; PRUNOTTO, Marco; RICHTER, Hans; RITTER, Martin; (217 pag.)WO2017/137334; (2017); A1;,
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Pyrimidine – Wikipedia

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 4595-60-2, name is 2-Bromopyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of 2-Bromopyrimidine

General procedure: A Schlenk flask was charged with the catalyst, NaOt-Buand aryl halide, if solid, and the flask was evacuated and backfilled with nitrogen three times. Subsequently, a solution of the aryl halide, if liquid, and the amine in toluene was added. The resulting reaction mixture was stirred under nitrogen at the indicated temperature and time (see Tables incommunication). The crude mixture was absorbed onto silica gel (Merck Silica Gel 60 (0.040-0.063 mm)) and purified by flash column chromatography (MTBE/40-60 petroleum ether eluent).

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, 4595-60-2, 2-Bromopyrimidine.

Reference:
Patent; Johnson Matthey Public Limited Company; Colacot, Thomas John; Johansson Seechum, Carin; Parisel, Sebastien Laurent; (29 pag.)US10167305; (2019); B2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 1004-39-3, name is 4,6-Diaminopyrimidine-2-thiol. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C4H6N4S

To a flask equipped with a magnetic stirrer added 4,6-diamino-2-mercaptopyrimidine (1.4218g, 0.01mmol). It was dissolved in 40mL of methanol and added 42mL 0.25M aqueous sodium hydroxide solution. The above aqueous solution was added to the flask and stirred for 2 hours at room temperature to give the sodium salt of a mercapto group. After completion of the reaction, vacuum distillation and vacuum drying was used overnight. The dried Mercapto sodium salt was dissolved in 60mL of N, N- dimethylformamide (DMF) and Added in Step 2) obtained 4′-(1-bromo-2-ethoxy)-4-methoxyazobenzene (3.6745g, 0.11mmol), stirred at room temperature for 24h. After completion of the reaction, ethyl acetate was added then dried overnight over anhydrous magnesium sulfate, filtered and rotary evaporated to remove residual solvent. The crude product was further purified by silica gel column chromatography and finally get a diamine containing Azo-Pyrimidine monomer

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, 1004-39-3, 4,6-Diaminopyrimidine-2-thiol.

Reference:
Patent; Yidun New Materials (Suzhou) Co., Ltd.; Lu, Qinghua; Tong, Faqin; (24 pag.)CN105693625; (2016); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 63200-54-4, Adding some certain compound to certain chemical reactions, such as: 63200-54-4, name is 2,4-Dichloro-5H-pyrrolo[3,2-d]pyrimidine,molecular formula is C6H3Cl2N3, 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 63200-54-4.

2,4-Dichloro-5H-pyrrolo[3,2-d]pyrimidine (376 mg, 2 mmol), 13 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (832 mg, 4 mmol), anhydrous 14 copper acetate (363 mg, 2 mmol), and 15 pyridine (158 mg, 2 mmol) were added into 16 dimethylsulfoxide (10 mL). The reaction liquid was heated to 110 C and stirred overnight. The reaction liquid was naturally cooled down to room temperature, followed by adding 17 ethyl acetate (50 mL). The insolubles were removed by filtration. The filtrate was washed with water (40 mL × 2), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was beaten in a mixed solution of 18 n-hexane / ethyl acetate (2/1, 30 mL), and filtered to give 150 mg of a pale yellow solid. Yield: 28.0%. MS (ESI, m/z): [M+H]+: 267.9.

According to the analysis of related databases, 63200-54-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Beijing Hanmi Pharmaceutical Co., Ltd.; XU, Jiangcheng; CAI, Qingyuan; CHA, Mi Young; KIM, Maengsup; (85 pag.)EP3336090; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 36082-45-8, 2-Amino-5-bromo-4-methoxypyrimidine, 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: C5H6BrN3O, blongs to pyrimidines compound. Formula: C5H6BrN3O

Intermediate U: 4-Methoxy-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyrimidin-2-ylamine A mixture of 2-amino-5-bromo-4-methoxypyrimidine [36082-45-8] (11.1 mmol), bis(pinacolato)diboron (12.2 mmol), PdCl2(dppf).CH2Cl2 adduct (0.555 mmol) and potassium acetate (33.3 mmol) in dioxane (60 mL) was stirred at 115 C. under argon for 20 h, allowed to cool to rt, diluted with toluene (60 mL), sonicated, and filtered through celite. The celite cake was rinsed with hot toluene (2*). The filtrate was concentrated to afford the title compound (30% purity) which was used without purification. ESI-MS: tR=0.22 min; [M+H]+ 170 (boronic acid) (LC-MS 1).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,36082-45-8, 2-Amino-5-bromo-4-methoxypyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; Cotesta, Simona; Furet, Pascal; Guagnano, Vito; Holzer, Philipp; Kallen, Joerg; Mah, Robert; Masuya, Keiichi; Schlapbach, Achim; Stutz, Stefan; Vaupel, Andrea; US2013/317024; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 149849-94-5, Methyl 2-chloropyrimidine-4-carboxylate, 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, 149849-94-5, blongs to pyrimidines compound. Quality Control of Methyl 2-chloropyrimidine-4-carboxylate

To the solution of 1860 mg methyl 2-chloropyrimidine-4-carboxylate (10.78 mmol) in 11 mL THF 21.6 mL DIBAL-il (lM in THF, 21.6 mrnol) was added dropwise at -70C and it was stirred at this temperature for 16 h. 5 mL MeOH was added to it at -50C, then 5 mLwater was added to it at 0C. It was filtered through celite. The filtrate was concentrated under reduced pressure, aM then it was purified via flash chromatography using heptanc and EtOAe as eluents.?H NMR (200 MHz, CDCI3): 8.60 (d, 111), 7.38 (d, lH), 4.79 (s, 211).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,149849-94-5, its application will become more common.

Reference:
Patent; LES LABORATOIRES SERVIER; VERNALIS (R&D) LIMITED; KOTSCHY, Andras; SZLAVIK, Zoltan; CSEKEI, Marton; PACZAL, Attila; SZABO, Zoltan; SIPOS, Szabolcs; RADICS, Gabor; PROSZENYAK, Agnes; BALINT, Balazs; BRUNO, Alain; GENESTE, Olivier; DAVIDSON, James Edward Paul; MURRAY, James Brooke; CHEN, I-Jen; PERRON-SIERRA, Francoise; WO2015/97123; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 923282-64-8, 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. 923282-64-8, name is 7-Chloro-1H-pyrazolo[4,3-d]pyrimidine, molecular formula is C5H3ClN4, 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.

(S)-2-amino-4-(((R)-2-methoxypropyl) (4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl) butyl)amino) butanoic acid acetate (100 mg, 241 mumol) in 4:1 THF/H2O (2.5 mL) was added NaHCO3 (57 mg, 684 mumol) followed by 7-chloro-1H-pyrazolo[4,3-d]pyrimidine (45 mg, 289 mumol) and the resulting mixture was stirred at 70 C. for 12 h. The mixture was cooled to rt and then adjusted to pH=6 by aq. 1 M HCl and then concentrated in vacuo. The resulting crude residue was purified by reverse phaseprep-HPLC to give the title compound. LCMS (ESI+): m/z=497.3 (M+H)+. 1H NMR (400 MHz, Methanol-d4) delta ppm 8.18-8.48 (m, 2H) 7.60 (d, J=7.21 Hz, 1H) 6.59 (d, J=7.21 Hz, 1H) 4.87 (br s, 1H) 3.73 (br s, 1H) 3.41 (br s, 2H) 3.25-3.37 (m, 1H) 3.19-3.24 (m, 3H) 3.02-3.19 (m, 5H) 2.63-2.77 (m, 4H) 2.33 (br s, 1H) 2.20 (br d, J=10.15 Hz, 1H) 1.59-1.87 (m, 6H) 1.10 (br d, J=5.87 Hz, 3H).

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 923282-64-8, 7-Chloro-1H-pyrazolo[4,3-d]pyrimidine.

Reference:
Patent; Pliant Therapeutics, Inc.; CHA, Jacob; DONG, Chengguo; HOM, Timothy; JIANG, Lan; LEFTHERIS, Katerina; LI, Hui; MORGANS, JR., David J.; MUNOZ, Manuel; REILLY, Maureen; ZHENG, Yajun; (232 pag.)US2019/276449; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia