Tag: M.W:100-200

Application of 56621-91-1, 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. 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.

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

According to the analysis of related databases, 56621-91-1, the application of this compound in the production field has become more and more popular.

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

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. 99420-75-4, name is 5-Methylpyrimidine-2-carboxylic acid, the common compound, a new synthetic route is introduced below. COA of Formula: C6H6N2O2

To a solution of 5-methylpyrimidine-2-carboxylic acid (1 g, 7.24 mmol) in DMF (72.4 mL) was added 5-methylpyrimidine-2-carboxylic acid (1 g, 7.24mmol), and N,O- dimethylhydroxylamine hydrochloride (0.777 g, 7.96 mmol). The mixture was cooled to 0oC and 1-propanephosphonic acid cyclic anhydride (50 wt. % solution in EtOAc, 9.21 mL, 14.48 mmol) was added droppwise. The mixture was allowed to warm to RT overnight. LCMS indicated complete conversion to product. The mixture was then diluted with water, extracted with CHCl3:IPA (3:1), and washed with brine and NaHCO3. The mixture was dried over Na2SO4, concentrated in vacuo, and purified by silica gel chromatography (0-100% heptanes:EtOAc) to yield N-methoxy-N,5-dimethylpyrimidine- 2-carboxamide (0.7 g, 3.86 mmol, 53.4 % yield), Example 142.1.1H NMR (500 MHz, CDCl3) delta 8.61 – 8.69 (m, 2 H) 3.61 – 3.79 (m, 3 H) 3.27 – 3.47 (m, 3 H) 2.34 – 2.45 (m, 3 H). LCMS-ESI (pos.) m/z: 182.2 (M+H)+.

The synthetic route of 99420-75-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; CHEN, Ning; CHEN, Xiaoqi; CHEN, Yinhong; CHENG, Alan C.; CONNORS, Richard V.; DEIGNAN, Jeffrey; DRANSFIELD, Paul John; DU, Xiaohui; FU, Zice; HARVEY, James S.; HEATH, Julie Anne; HEUMANN, Lars V.; HORNE, Daniel B.; HOUZE, Jonathan; KALLER, Matthew R.; KAYSER, Frank; KHAKOO, Aarif Yusuf; KOPECKY, David J.; LAI, Su-Jen; MA, Zhihua; MEDINA, Julio C.; MIHALIC, Jeffrey T.; NISHIMURA, Nobuko; OLSON, Steven H.; PATTAROPONG, Vatee; SWAMINATH, Gayathri; WANG, Xiaodong; WANSKA, Malgorzata; YANG, Kevin; YEH, Wen-Chen; (700 pag.)WO2018/97945; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
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Reference of 186519-92-6, 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 186519-92-6 as follows.

Svnthesis 8-1 -B; f-Butyl 3-(4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carboxamido)piperidine-1-carboxylate; A solution of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylic acid (18 mg, 0.09 mmol), HATU (45 mg, 0.12 mmol), and diisopropylethylamine (80 mul_, 0.46 mmol) in DMF (1 mL) was stirred at room temperature for 30 minutes. ferf-Butyl 3-aminopiperidine-1- carboxylate hydrochloride (28 mg, 0.12 mmol) in DMF (0.5 mL) was added and the resulting solution was stirred for 16 hours. The mixture was diluted with brine and extracted with ethyl acetate. The combined organic layers were washed sequentially with NaHCO3 solution, citric acid, and brine, then dried (Na2SO4), filtered, and concentrated. Purification by preparative TLC, eluting with ethyl acetate, gave the title compound as a light yellow oil (10 mg, 29%).1H NMR (500 MHz, CD3OD) delta 1.47 (9H, s), 1.49-1.69 (2H, m), 1.71-1.84 (1 H, m), 2.02- 2.11 (1 H, m), 3.13-3.27 (1 H, m), 3.54-3.68 (1 H, m), 3.86-3.96 (2H, m), 4.00-4.09 (1 H, m), 7.92 (1 H, s), 8.61 (1 H, s); LC-MS Rt 4.29 min; m/z (ESI) 380 [MH+].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,186519-92-6, its application will become more common.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; WO2008/75007; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 42839-08-7, 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. 42839-08-7, name is Ethyl pyrimidine-2-carboxylate. A new synthetic method of this compound is introduced below.

The 2 – (2 – methoxy phenoxy) malonamide (II) (35.0 g, 156.1 mmol) dissolved in ethanol (600 ml) in, are tertiary butanol sodium (30.0 g, 312.2 mmol) and 2 – pyrimidine formic acid ethyl ester (III) (23.8 g, 156.1 mmol), stirred under the protection of nitrogen reflux 1 h, TLC detection reaction is completed. Recovering the ethanol, the residue with water (200 ml) mixed beating, filtering, a little water to wash the filter cake, drying, to obtain compound 5 – (2 – methoxyphenoxy) – 1H – [2, 2′] – bipyridyl – 4, 6 – dione (IV) 40.5 g, yield is 83%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,42839-08-7, Ethyl pyrimidine-2-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Shanghai Tianci International Pharmaceutical Co., Ltd.; Li Xinjuanzi; Li Jianzhi; Ma Xilai; Chi Wangzhou; Liu Hai; Hu Xuhua; Zheng Xiaoli; Zhai Zhijun; Li Jianxun; (14 pag.)CN104193687; (2017); B;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 40497-30-1 ,Some common heterocyclic compound, 40497-30-1, molecular formula is C5H6N2O2, 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.

Preparation of 1,1-diamino-2,2-dinitroethylene from the nitric-sulfur mixed acid prepared from the nitric acid filtrate once recycledAt 20C, weigh 62.5g of the nitric acid filtrate once cycled, add 25.0g of fuming sulfuric acid with a mass fraction of 50% and 62.5g of nitric acid with a mass fraction of 98% in order to obtain 150.0g of mixed nitric acid;The nitric-sulfur mixed acid was cooled to 0 C, and 10.0 g of 2-methyl-4,6-pyrimidinedione was added in portions with stirring.Then warmed to 15C for 3h,After the reaction, the temperature was reduced to 0C, and the nitric acid filtrate was collected. The filter cake was added to 450 g of ice water. After filtering and drying, 10.2 g of 1,1-diamino-2,2-dinitroethylene was obtained, and the yield was 86.8%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,40497-30-1, its application will become more common.

Reference:
Patent; Xi’an Modern Chemical Institute; Zhou Cheng; Li Xiangzhi; Chang Pei; Wang Bozhou; Zhou Qun; Chen Tao; Li Yanan; (6 pag.)CN107602395; (2019); B;,
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Synthetic Route of 115932-00-8, 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. 115932-00-8, name is Ethyl pyrazolo[1,5-a]pyrimidine-3-carboxylate, molecular formula is C9H9N3O2, 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 solution of ethyl pyrazolo[l,5-a]pyrimidine-3-carboxylate (3.15 g, 16.4 mmol) in ethanol (50 mL) and water (40 mL) was added potassium hydroxide aqueous solution (2 M, 40 mL). The reaction mixture was stirred at 50 C for 2 h and cooled down to room temperature and then concentrated in vacuo. The resulting mixture was adjusted to pH = 2 with 1M hydrochloric acid aqueous solution, and white solid was appeared, then filtered to afford the product as a white solid (2.6 g, 97%).LC-MS (ESI, neg. ion) m/z: 162.1 [M-H] . H NMR (600 MHz, DMSO-Lambda): delta (ppm) 9.26 (dd, J= 7.0, 1.7 Hz, 1H), 8.80 (dd, J = 4.1, 1.7 Hz, 1H), 8.58 (s, 1H), 7.26 (dd, J= 7.0, 4.1 Hz, 1H).

According to the analysis of related databases, 115932-00-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CALITOR SCIENCES, LLC; SUNSHINE LAKE PHARMA CO., LTD.; XI, Ning; LI, Minxiong; LI, Xiaobo; WO2015/73267; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 1192064-63-3 , The common heterocyclic compound, 1192064-63-3, name is 2,5-Dichloro-4-methylpyrimidine, molecular formula is C5H4Cl2N2, 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 2,5-dichloro-4-methylpyrimidine (300 mg, 1.6 mmol), (R)-tert-butyl 3- aminopyrrolidine-l-carboxylate (263 mg, 1.6 mmol) and DIEA (619 mg, 4.8 mmol) in DMF (5 mL) was stirred at l20C for 5 hours. The mixture was cooled to RT, diluted with water (20 mL) and extracted with EtOAc (20 mL* 3). The combined organic phase was washed with brine (20 mL), dried over Na2S04, filtered and concentrated. The residue was purified by flash chromatography on silica gel (petroleum ether/EtOAc = 20/1) to afford (R)-tert-butyl 3-((5-chloro- 4-methylpyrimidin-2-yl)amino)pyrrolidine-l-carboxylate (250 mg, 50%) as a yellow solid. [M+H] Calc?d for Ci4H2iClN402, 313.1; Found, 313.1.

The synthetic route of 1192064-63-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KINNATE BIOPHARMA INC.; KANOUNI, Toufike; ARNOLD, Lee D.; KALDOR, Stephen W.; MURPHY, Eric A.; TYHONAS, John; (0 pag.)WO2020/6497; (2020); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 99420-75-4 ,Some common heterocyclic compound, 99420-75-4, molecular formula is C6H6N2O2, 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 5-methylpyrimidine-2-carboxylic acid (0.03 g, 0.22 mmol, 1 eq) and (S)-1-(pyrrolo[1,2-a]pyrazin-1-yl)pyrrolidin-3-amine (0.060 g, 0.22 mmol, 1 eq) in 1 mL of DMSO was added triethylamine (0.12 mL, 0.86 mmol, 4 eq) and HATU (0.09 g, 0.24 mmol, 1.1 eq). After stirring for 1 h at room temperature, the mixture was concentrated and purified by HPLC to afford (S)-5-methyl-N-(1-(pyrrolo[1,2-a]pyrazin-1-yl)pyrrolidin-3-yl)pyrimidine-2-carboxamide (0.029 g, 0.09 mmol, 41%). 1H NMR (400 MHz, CD3OD) delta 8.75 (s, 2H), 7.76 (s, 1H), 7.71 (d, J=5.5 Hz, 1H), 7.54 (s, 1H), 6.91 (s, 1H), 6.85 (d, J=5.8 Hz, 1H), 5.00-3.60 (br, 5H), 2.65-2.30 (br, 2H), 2.40 (s, 3H); MS: (ES) m/z calculated for C17H18N6O [M+H]+323.2. found 323.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,99420-75-4, its application will become more common.

Reference:
Patent; ChemoCentryx, Inc.; Fan, Junfa; Krasinski, Antoni; Lange, Christopher W.; Lui, Rebecca M.; McMahon, Jeffrey P.; Powers, Jay P.; Zeng, Yibin; Zhang, Penglie; US2014/154179; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 25746-87-6, 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 25746-87-6, name is 4-Dimethoxymethylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

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]+.

According to the analysis of related databases, 25746-87-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Buettelmann, Bernd; Jakob-Roetne, Roland; Knust, Henner; Thomas, Andrew; US2009/143385; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 3438-61-7, 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. 3438-61-7, name is 5-Amino-4-methylpyrimidine, molecular formula is C5H7N3, 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.

225.0 g (2.06 mol) of 4-methyl-5-aminopyrimidine was dissolved in 10.0 L of anhydrous THF in a dry flask under nitrogen blanket. The solution was cooled to -200C. 2.0 L (1.39 kg, 5.00 mol) of 2.5 M «-BuLi in hexane was added in 20 minutes while the temperature was kept below -50C. The mixture was agitated at below -15C for 30 minutes and then warmed up to normal room temperature (RT) and stirred for 3 hours. 250.0 g (0.61 mol) of the above methyl ester from stage 7, in 250 mL of anhydrous THF, was added over 25 minutes while the temperature was kept below 350C. The light yellow slurry turned to a dark solution. The solution was stirred for 20 minutes. A reaction sample was quenched with MeOH and analyzed by HPLC to make certain that there is no starting methyl ester left. The solution was then cooled back to below 150C. 2.0 L of MeOH was added over 10 minutes while the temperature was kept below 250C followed by 1.0 L of water added in one portion and the mixture was allowed to warm up to room temperature and stir for 15 hours. A reaction sample was analyzed by HPLC to make certain all related intermediates have been converted. The mixture was cooled to below 200C. 1.2 L of 6 N hydrochloric acid was added over 35 minutes while the temperature was kept below 250C. The solution was agitated for 1 hour. The reaction was monitored by HPLC to make certain that all related intermediates had been converted. The solution was cooled to below 150C. 6 N of NaOH was added to adjust the solution pH to 7-8 (about 370 mL was needed). Most solvents (14.5 L) were removed under vacuum (140 mmHg) and 4.0 L of EtOAc and 2.0 L of water were added. Layers were separated and the organic layer was washed with three 2.0 L portions of water and 1.0 L of brine. The solvent was removed under vacuum from the organic layer to yield 450.0 g of a thick dark brown oil as the crude product. The residue was chased with 500 mL of «-propanol to get 393.2 g of a thick slurry. 500 mL of «-propanol was added and the mixture was heated up to 600C to dissolve the solid. The solution was cooled down with agitation and the slurry was filtered after 16 hours at room temperature and the solid was washed with the filtrate and two 100 mL portions of n- propanol and two 200 mL portions of hexane and air dried to yield the title compound (R)- 1,1,1 -trifluoro-4-(5-fluoro-2-methylphenyl)-4-methyl-2-(5H-pyrrolo[3,2-rf]pyrimidin-6- ylmethyl)pentan-2-ol «-propanol solvate as a light yellow solid, 140.2 g, 44% yield.

According to the analysis of related databases, 3438-61-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG; WO2009/134737; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia