Tag: M.W:100-200

Reference of 19808-30-1, 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 19808-30-1, name is 5-Bromopyrimidin-4(3H)-one. This compound has unique chemical properties. The synthetic route is as follows.

Step T1: 5-Bromo-4-methoxy-pyrimidine A mixture of 5-bromo-3H-pyrimidin-4-one (Step T2) (17.9 mmol) and POCI3 (179 mmol) was stirred at 80 C. for 1 h and concentrated. The residue was dissolved in CH2Cl2 (30 mL) and cooled to 5 C. MeOH (20 mL) was added and the mixture was stirred for at rt 1 h and concentrated. The residue was triturated in CH2Cl2 to afford the title compound as a white solid. ESI-MS: [M+H]+ 189/191 (MS 1).

According to the analysis of related databases, 19808-30-1, the application of this compound in the production field has become more and more popular.

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

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. 114969-66-3, name is 5-Bromo-4-cyanopyrimidine. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C5H2BrN3

GENERAL PROCEDURE B: Amination of Heteroaryl Halides; i) BOC-Piperazine (2.4 mmol), 5-bromopyrimidine-4-carbonitrile (2 mmol), potassium carbonate (2.8 mmol), 2-dicyclohexylphosphino-2′,4′,6’triisopropyl-biphenyl (0.16 mmol), and tris(dibenzylideneacetone)dipalladium(0) (0.04 mmol) were dissolved in NMP (N-Methylpyrrolidinone) (5 mL) and stirred for 10 min at 200 C. The cooled mixture was diluted with ethyl acetate, and washed with water. The organic layer was dried, filtered and concentrated, then chromatography in 20-50% ethyl acetate in hexane yielded the desired BOC-protected intermediate. Note: The same procedure was used to prepare tert-butyl 4-(5-cyanopyrazin-2-yl)piperazine-1-carboxylate from 5-bromopyrazine-2-carbonitrile except that the reaction was carried out in DMF for 4 h. at 85 C.

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, 114969-66-3, 5-Bromo-4-cyanopyrimidine.

Reference:
Patent; AstraZeneca AB; NPS PHARMACEUTICALS, INC.; US2007/37820; (2007); A1;,
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. 56621-91-1, name is 5-Amino-2-bromopyrimidine, molecular formula is C4H4BrN3, 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. HPLC of Formula: C4H4BrN3

To a solution of 2-bromopyrimidin-5-amine (3.0 g, 23 mmol) in fert-BuOH (46 mL) was added Boc20 (8.0 mL, 34 mmol). The reaction was stirred at 60 C for two days, after which additional Boc20 (8.0 mL, 34 mmol) was added and the reaction was kept at 60 C for two days. Upon completion, the solvent was evaporated in vacuo and the residue was purified by flash chromatography (MPLC, 10-100% EtOAc-hexanes) to give terr-butyl (2-bromopyrimidin- 5-yl)carbamate.LRMS (ESI) calc’d for C9H13BrN302_[M+H]+: 274, Found: 274

With the rapid development of chemical substances, we look forward to future research findings about 56621-91-1.

Reference:
Patent; MERCK SHARP & DOHME CORP.; YOUNG, Jonathan; CZAKO, Barbara; ALTMAN, Michael; GUERIN, David; MARTINEZ, Michelle; RIVKIN, Alexey; WILSON, Kevin; LIPFORD, Kathryn; WHITE, Catherine; SURDI, Laura; CHICHETTI, Stephanie; DANIELS, Matthew, H.; AHEARN, Sean, P.; FALCONE, Danielle; OSIMBONI, Ekundayo; WO2011/84402; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 25746-87-6, 4-Dimethoxymethylpyrimidine, 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, 25746-87-6, blongs to pyrimidines compound. name: 4-Dimethoxymethylpyrimidine

c) Pyrimidine-4-carbaldehyde A solution of 4-dimethoxymethyl-pyrimidine (30.6 g, 199 mmol) in water (235 mL) and concentrated sulfuric acid (2.9 g, 30 mmol) was heated at 60 C. for 24 h. After cooling to room temperature the pH was set to 8 with saturated aqueous sodium hydrogen carbonate solution. The mixture was then extracted overnight in a continuous extraction (Keberle) for 48 h with chloroform. The chloroform extract was then dried over sodium sulfate, filtered and evaporated. Purification by chromatography (SiO2, dichloromethane_methanol=1:0 to 95:5) afforded the title compound (8.1 g, 26%) which was obtained as a brown oil. MS: m/e=108.0 [M]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,25746-87-6, its application will become more common.

Reference:
Patent; Buettelmann, Bernd; Jakob-Roetne, Roland; Knust, Henner; Thomas, Andrew; US2009/143385; (2009); 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.3270-97-1, name is 2,4-Diamino-6-methoxypyrimidine, molecular formula is C5H8N4O, molecular weight is 140.14, as common compound, the synthetic route is as follows.Computed Properties of C5H8N4O

2,4-Diamino-6-chloropyrimidine (17.34 g: 120 mmol) and sodium methoxide (38.9 g) were sequentially added to t-butanol (60 mL) and N-ethylpyrrolidone (30 mL) under a nitrogen gas flow, followed by stirring with heating at 80 C. for 2 hours. The reaction solution was cooled to 60 C., and methyl benzoate (38.9 g: 288 mol) was dropwise added thereto, followed by stirring with heating at 60 C. for 2 hours. The reaction solution was added to a liquid mixture of iced water (130 mL) and concentrated hydrochloric acid (51 mL), followed by heating to 50 C. to completely dissolve the solid component. The organic layer was separated, and methanol (100 mL) and water (100 mL) were added thereto, followed by stirring under ice cooling for 1 hour. The precipitated product was collected by filtration, and the resulting crystals were washed with a poured methanol/water solvent mixture and then water. After ventilation drying at 50 C. for 13 hours, 38 g (yield: 85%) of compound (1-9) was yielded.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,3270-97-1, 2,4-Diamino-6-methoxypyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; FUJIFILM Corporation; YAMAMOTO, Aiko; TANAKA, Satoshi; NIORI, Teruki; NAGURA, Masato; NORO, Masaki; YOSHIDA, Aiko; FUKAGAWA, Nobutaka; KUWAYAMA, Yasukazu; (89 pag.)US2016/159750; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 206564-00-3, Adding some certain compound to certain chemical reactions, such as: 206564-00-3, name is 4-(2-Furyl)pyrimidin-2-amine,molecular formula is C8H7N3O, 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 206564-00-3.

General procedure: The mixture of 8 (1.0 equiv) and 2-amino-pyrimidine derivatives 4-6 (1.0 equiv) in toluene was heated to reflux. Along with the azeotrope of ethanol and toluene was distilled out of the reaction system continuously, a small amount of fresh toluene was added if necessary. Heating was stopped until the complete consumption of 8 which was indicated by TLC. After the reaction mixture was cooled to room temperature, the forming precipitate was collected by suction filtration and washed with small amounts of toluene and ethyl acetate to afford desired compounds 9-11. They could be further purified on silica gel column chromatography (eluted by acetone with petroleum ether).

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. 206564-00-3, 4-(2-Furyl)pyrimidin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Chen, Wei; Li, Yuxin; Zhou, Yunyun; Ma, Yi; Li, Zhengming; Chinese Chemical Letters; vol. 30; 12; (2019); p. 2160 – 2162;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 52854-14-5, 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 52854-14-5, name is 4-Chloro-6-methoxy-5-nitropyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

The above product (3.50 g, 18.5 mmol) and 3′-aminobiphenyl-2-carbonitrile (prepared according to the procedure described in WO 02/38568) (3.23 g, 16.6 mmol) were dissolved in triethylamine (9. 32 g, 92.3 mmol) and dimethylsulfoxide (10 ml) and heated at 90C for 18 h. The mixture was allowed to cool to ambient temperature then poured onto water (150 ml) and extracted with ethyl acetate (2 x 300 ml). The organic fractions were combined, washed with water (3 x 75 ml) and brine (50 ml), dried over anhydrous sodium sulfate, filtered and evaporated to give a brown solid. The brown solid was triturated with diethyl ether (50 ml), filtered, washed with diethyl ether (2 x 10 ml) and left to air dry, which gave 3′- (1-methyl-5-nitro-6-oxo-1, 6-DIHYDROPYRIMIDIN-4-YLAMINO) biphenyl-2-carbonitrile (2.24 g, 38%) as a yellow solid

According to the analysis of related databases, 52854-14-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME LIMITED; WO2004/41826; (2004); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 1193-21-1, 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. 1193-21-1, name is 4,6-Dichloropyrimidine, molecular formula is C4H2Cl2N2, 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.

(9) Synthesis of intermediate (c’) 298 mL of methanol is added to 387 mL (7.98 mol) of hydrazine monohydrate, followed by cooling to 10C (internal temperature). To the resulting mixture is gradually added 149 g (1.00 mol) of 4,6-dichloropyrimidine (at an internal temperature of 20C or lower), and then the ice bath is removed to allow the internal temperature to increase to room temperature, followed by stirring the mixture for 30 minutes at the same temperature. Thereafter, the mixture is further heated to an internal temperature of 60C, and stirred for 5 hours at the same temperature. After completion of the reaction, 750 mL of water is added thereto, and the reaction solution is cooled with ice to an internal temperature of 8C. Crystals precipitated are collected by filtration, spray washed with water and with isopropanol, and dried for 36 hours at room temperature to obtain 119 g (white powder; yield: 84.5%) of the intermediate (c’). Results of NMR measurement of the thus-obtained intermediate (c’) are as follows. 1H-NMR (300 MHz, d-DMSO): 7.80 (s, 1H), 7.52 (s, 2H), 5.98 (s, 1H), 4.13 (s, 4H)

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 1193-21-1, 4,6-Dichloropyrimidine.

Reference:
Patent; FUJIFILM Corporation; EP2474576; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 1119280-66-8, 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 1119280-66-8 as follows.

step 1 : To a stirred mixture of sodium hydride (12.5 g, 520 mmol, 60% in mineral oil) in anhydrous THF (300 mL) at 0 C was added dropwise 2-chloro-5H-pyrrolo[3,2-d]pyrimidine (40.0 g, 262 mmol) dissolved in anhydrous THF (200 mL). The reaction mixture was stirred at 0 C for 15 min them SEMCl (52.5 g, 315 mmol) was added dropwise. The mixture was then stirred at RT for 1 h and then diluted with EtOAc. The organic layer was washed with water and brine, dried(Na2S04), filtered and concentrated under reduced pressure. The crude product was purified by Si02 chromatography to afford 42 g (56.4%o) of 2-chloro-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[3,2-i ]pyrimidine as an orange oil. A high-pressure tube charged with 2-chloro-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[3,2- i ]pyrimidine (2.23 g, 7.90 mmol), tributyl(l-ethoxyvinyl)stannane (3.7 g, 10.27 mmol), and Pd(PPh3)2Cl2 (200 mg) in degassed DMF (20 mL) under N2 was sealed and heated at 100 C for 16 h. The reaction mixture was cooled, diluted with EtOAc, and filtered through a pad of Celite to remove Pd solid. The filtrate was washed with water and brine, dried (Na2S04), filtered, and concentrated under reduced pressure. The crude product was dissolved in anhydrous THF (0.3 M), and 2N HC1 (5.0 eq.) was added. The reaction mixture was stirred at RT under N2 for 16 h, poured into 10% aq. NaOH solution, and then extracted with EtOAc. The organic layer was washed with water and brine, dried (Na2S04), filtered, and concentrated under reduced pressure. The crude product was purified by Si02 chromatography to afford 1.5 g (66%) of l-(5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[3,2-d]pyrimidin-2-yl)ethanone as pale yellow solid. 1H NMR (400 MHz, CDCl3) delta 9.09 (s, 1H), 7.66 (d, J = 3.2 Hz, 1H), 6.89 (d, J = 4.8 Hz, 1H), 5.60 (s, 2H), 3.49 (t, J = 8.0 Hz, 2H), 2.88 (s, 3H), 0.901 (t, J = 8.0 Hz, 2H), -0.053 (s, 9H); MS(ESI) m/z: 291 [M+].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1119280-66-8, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; ALIAGAS-MARTIN, Ignacio; CRAWFORD, James John; MATHIEU, Simon; RUDOLPH, Joachim; LEE, Wendy; WO2013/92940; (2013); 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