Month: March 2022

Application of 886365-79-3, 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 886365-79-3 as follows.

A mixture of 0.5 g (2.48 mmol) 5-bromo-N,N-dimethyl-pyrimidin-2-amine, 0.8 g (3.24 mmol) bis(pinacolato)diborone, 0.6 g (6.38 mmol) KOAc, 0.2 g (0.25 mmol) (0358) Pd(dppf)CI2 * DCM and dioxane is heated to 100C for 4.5 h. After cooling to RT, the reaction mixture is filtered through a pad of Celite and evorated, water is added and the mixture is extracted with EtOAc. The organic phases are pooled, dried and evaporated The crude product is purified by FC. (0359) Yield: 0.6 g (96%), ESI-MS: m/z = 250 (M+H)+, Rt(HPLC): 0.22 min (HPLC-A)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,886365-79-3, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BLUM, Andreas; GODBOUT, Cedrickx; HEHN, Joerg, P.; PETERS, Stefan; (74 pag.)WO2017/194453; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 675-11-6, 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. 675-11-6, name is 4,6-Difluoropyrimidin-2-amine. A new synthetic method of this compound is introduced below.

EXAMPLE 9 Preparation of 2-amino-6-(4-chlorophenoxy)-4-fluoropyrimidine (Variant A) STR17 2.52 g (0.038 mol) of 85% sodium hydroxide were dissolved in 50 ml of methanol, 4.9 g (0.0382 mol) of 4-chlorophenol were added, and the mixture was evaporated to dryness. The residue of salt obtained in this way was taken up in 50 ml of N-methyl-2-pyrrolidone and, at 25 C., 5.0 g (0.0382 mol) of 2-amino-4,6-difluoropyrimidine were added, and the mixture was stirred at 140 C. for 4 hours. After the reaction mixture had been cooled to 25 C. it was stirred into 500 ml of water, and the resulting precipitate was isolated. 7.4 g (81% of theory) of the title compound of melting point 223-226 C. were obtained in this way.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,675-11-6, 4,6-Difluoropyrimidin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; BASF Aktiengesellschaft; US5011927; (1991); 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. 19858-50-5, name is (2-(Methylthio)pyrimidin-5-yl)methanol, molecular formula is C6H8N2OS, 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. Quality Control of (2-(Methylthio)pyrimidin-5-yl)methanol

To the solution of (2-(methylthio)pyrimidin-5-yl)methanol (0.88 g, 5.6 mmol) in DCM (20 ml) at 0°C was added triphenylphosphine (2.1 g, 7.9 mmol) and carbon tetrabromide(2.6 g, 7.9 mmol). The resulting solution was stirred at 0°C for 1 hour. The reaction mixture was purified on silica gel column using EtOAc/hexane as eluting solvents to give 5- (bromomethyl)-2-(methylthio)pyrimidine. LC/MS: (M+ 1 ): 218.90; 220.90.

With the rapid development of chemical substances, we look forward to future research findings about 19858-50-5.

Reference:
Patent; MERCK SHARP & DOHME CORP.; TANG, Haifeng; YANG, Shu-Wei; MANDAL, Mihir; SU, Jing; LI, Guoqing; PAN, Weidong; TANG, Haiqun; DEJESUS, Reynalda; PAN, Jianping; HAGMANN, William; DING, Fa-Xiang; XIAO, Li; PASTERNAK, Alexander; HUANG, Yuhua; DONG, Shuzhi; YANG, Dexi; WO2015/171474; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 74840-34-9, 4-Chloro-2-(methylthio)pyrimidine-5-carboxylic acid, 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, 74840-34-9, blongs to pyrimidines compound. Computed Properties of C6H5ClN2O2S

A solution of 4-chloro-2-methylthio-5-pyrimidinecarboxylate (900 mg, 3.87 mmol) (Aldrich) and triethylamine (1.1 ML, 870 mg, 7.74 mmol) (Aldrich) in dioxane (50 ML) was treated with (+-)-trans-3-(tert-butyl-dimethyl-silanyloxy)-cyclopentylamine (840 mg, 3.87 mmol) (from Example 9c supra).The mixture was stirred at reflux for 1 hour, then cooled and partitioned between brine and ethyl acetate.The organic layer was collected, dried over sodium sulfate, filtered and concentrated to a residue that was purified by silica gel column chromatography using a 0-20percent ethyl acetate in hexanes gradient.The product isolated from this purification was then dissolved in anhydrous tetrahydrofuran (80 ML) and the resulting solution was cooled to 0° C. Followed addition in-portions of lithium aluminum hydride (440 mg, 11.61 mmol) (Aldrich) and the resulting mixture was allowed to warm to room temperature.After overnight stirring the reaction mixture was poured slowly into a vigorously stirred mixture of ethyl acetate and saturated aqueous potassium sodium tartrate solution.The organic layer was collected, dried over sodium sulfate, filtered and concentrated to an off white solid.This intermediate was then dissolved in dichloromethane (80 ML) and the resulting solution was treated with manganese dioxide (3.36 g, 38.70 mmol) (Aldrich).After overnight stirring the solids were filtered off, washed with tetrahydrofuran (approximately 30 ML) and the combined organic layer was concentrated to a residue that upon a silica gel column purification with 0-50percent diethyl ether in hexanes gradient gave (+-)-4-[trans-3-(tert-butyl-dimethyl-silanyloxy)-cyclopentylamino]-2-methylsulfanyl-pyrimidine-5-carbaldehyde as a viscous colorless oil. (Yield 888 mg, 62percent). HRMS m/z calcd for C17H29N3O2SSi [M+H]+: 368.1823. Found:368.1826.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,74840-34-9, its application will become more common.

Reference:
Patent; Chen, Yi; Dermatakis, Apostolos; Liu, Jin-Jun; Luk, Kin-Chun; Michoud, Christophe; Rossman, Pamela Loreen; US2004/204427; (2004); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 923282-39-7 ,Some common heterocyclic compound, 923282-39-7, molecular formula is C6H5ClN4, 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 2-[3-methoxy-4-[[2-(trifluoromethyl)-4-pyridyl]oxy]phenyl]ethanamine (0.39 g, 1.2 mmol) in acetonitrile (30 mL) was added triethylamine (1.5 g, 4.8 mmol). The solution was stirred for 5 min at room temperature at which time 7-chloro-1-methyl-pyrazolo[4,3-d]pyrimidine (0.25 g, 1.2 mmol) was added. The reaction mixture was stirred at room temperature overnight. Water was added and was extracted with ethyl acetate (3*). The combined organic layers were washed with water, dried over Na2SO4 and concentrated in vacuo. The residue was purified by HPLC to provide 85 mg (0.19 mmol, 17%) of the product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,923282-39-7, its application will become more common.

Reference:
Patent; BASF SE; Grammenos, Wassilios; Craig, Ian Robert; Boudet, Nadege; Mueller, Bernd; Dietz, Jochen; Lauterwasser, Erica May Wilson; Lohmann, Jan Klaas; Montag, Jurith; US2014/371065; (2014); 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. 93587-23-6, name is 7-Bromo-1H-pyrrolo[3,2-d]pyrimidin-4(5H)-one, molecular formula is C6H4BrN3O, 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. Safety of 7-Bromo-1H-pyrrolo[3,2-d]pyrimidin-4(5H)-one

Intermediate 98 (1.30 g, 6.07 mmol) was suspended in POCl3 (60 mL) and heated at 115 C. for 3 h. The reaction mixture was cooled to r.t. and poured cautiously onto ice (300 mL). The reaction mixture was basified with K2CO3 and extracted with EtOAc (3*200 mL). The combined organic fractions were dried (MgSO4) and concentrated in vacuo to give the title compound as a beige solid (490 mg, 35%). LCMS (ES+): 231.9, 233.9, 235.9 (M+H)+.

With the rapid development of chemical substances, we look forward to future research findings about 93587-23-6.

Reference:
Patent; PROXIMAGEN LIMITED; Evans, David; Carley, Allison; Stewart, Alison; Higginbottom, Michael; Savory, Edward; Simpson, Iain; Nilsson, Marianne; Haraldsson, Martin; Nordling, Erik; Koolmeister, Tobias; US2013/102587; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 29133-99-1, 4,6-Dichloro-2,5-diphenylpyrimidine, 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, Product Details of 29133-99-1, blongs to pyrimidines compound. Product Details of 29133-99-1

Under N2, to the solution of cinchonidine (294.4 mg, 1.0 mmol) and 4,6-dichloro-2,5-diphenylpyrimidine (301.3 mg, 1.0 mmol) in PhMe (20 mL) was added powdered KOH (840.0 mg, 15 mmol) portionwise. The suspension was heated to 90 C. for 10 mins and then refluxed for another 50 mins. Then the resulting mixture was cooled down to room temperature and diluted with water (10 mL). The organic layer was separated. Next the aqueous layer was extracted with CH2Cl2 (10 mL×3). The combined organic extracts were washed with brine (20 mL), dried over Na2SO4 and concentrated under vacuum. The yellow residue was applied to column (CH2Cl2/MeOH=100/1 to 10/1) to afford CD-S1 as a white solid (462.5 mg, 83% yield). [alpha]D20=+164.8 (c=0.46, CHCl3). 1H NMR (400 MHz, CDCl3) delta 8.84 (d, J=4.5 Hz, 1H), 8.28 (d, J=8.4 Hz, 1H), 8.17 (d, J=8.3 Hz, 1H), 7.90 (d, J=7.4 Hz, 2H), 7.79 (t, J=7.6 Hz, 1H), 7.68 (t, J=7.6 Hz, 1H), 7.57 (t, J=7.2 Hz, 2H), 7.53-7.44 (m, 3H), 7.35-7.28 (m, 2H), 7.18 (t, J=7.7 Hz, 2H), 7.03 (d, J=3.5 Hz, 1H), 5.72-5.58 (m, 1H), 4.88 (t, J=13.4 Hz, 2H), 3.20-3.12 (m, 1H), 3.12-2.97 (m, 2H), 2.67-2.51 (m, 2H), 2.18 (s, 1H), 1.65 (d, J=2.6 Hz, 1H), 1.54 (dd, J=16.4, 9.5 Hz, 2H), 1.23 (dd, J=15.1, 8.2 Hz, 1H), 1.10-0.94 (m, 1H). 13C NMR (100 MHz, CDCl3) delta 166.4, 162.7, 150.1, 148.6, 145.8, 141.8, 135.6, 132.1, 131.3, 130.8, 130.1, 129.5, 128.7, 128.7, 128.4, 128.3, 127.1, 125.6, 123.2, 118.9, 117.6, 114.5, 78.2, 59.9, 57.4, 43.4, 39.9, 27.8, 27.2, 22.3; IR (CHCl3) v 2942, 2868, 1568, 1516, 1406, 1288, 1216, 1069, 1019, 993, 844, 756, 699 cm-1. HRMS (ESI/[M+H]+) Calcd. for C35H32N4OCl m/z 559.2265, found m/z 559.2263.

The synthetic route of 29133-99-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRANDEIS UNIVERSITY; WU, YONGWEI; DENG, LI; (65 pag.)US2020/48243; (2020); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products 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 (1 g, 7.24 mmol) in DMF (72.4 ml) was added 5-methylpyrimidine-2-carboxylic acid (1 g, 7.24mmol), and N,0- dimethylhydroxylamine hydrochloride (0.777 g, 7.96 mmol). The mixture was cooled to 0 C 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 diluted with water, extracted with CHC13:IPA (3: 1) and washed with brine and NaHC03. The mixture was dried over Na2S04, concentrated in vacuo and purified by silica gel chromatography (0-100% heptane s:EtO Ac) to yield N-methoxy-N,5-dimethylpyrimidine- 2-carboxamide (0.7 g, 3.86 mmol, 53.4 % yield). NMR (500 MHz, CDC13) 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 +.

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; AMGEN INC.; CHEN, Yinhong; DEBENEDETTO, Mikkel V.; DRANSFIELD, Paul John; HARVEY, James S.; HOUZE, Jonathan; KHAKOO, Aarif Yusuf; LAI, Su-Jen; MA, Zhihua; NISHIMURA, Nobuko; PATTAROPONG, Vatee; SWAMINATH, Gayathri; YEH, Wen-Chen; RAMSDEN, Philip Dean; SHARMA, Ankit; (321 pag.)WO2018/93576; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 1513-69-5, 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 1513-69-5 as follows.

Example 15: 4-chloro-6-(trifluoromethyl)pyrimidin-2-amine (24)2-Amino-6-(trifluoromethyl)pyrimidin-4-ol (200 mg, 1.1 mmol) is dissolved in POCI3 (3 eq., 0.3 ml_, 3.3 mmol) and dimethylaniline (0.28 ml_, 2 eq.) is added. The reaction mixture is heated at 7O0C for 4 h. The resulting mixture is poured into a mixture of ice-water, and the resulting precipitate is collected to yield the desired compound 24 in 59%. ESI-MS m/z 198 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1513-69-5, its application will become more common.

Reference:
Patent; COVALYS BIOSCIENCES AG; WO2006/114409; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 199678-12-1, Adding some certain compound to certain chemical reactions, such as: 199678-12-1, name is 4-Pyrimidin-2-yl-benzoic acid,molecular formula is C11H8N2O2, 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 199678-12-1.

Under an argon atmosphere, diethyl cyanophosphonate (0.27 mL, 1.80 mmol) and triethylamine (0.52 mL, 3.75 mmol) were added to a solution of compound 12 (303 mg, 1.50 mmol) and 4-pyrimidin-2-ylbenzoic acid (300 mg, 1.50 mmol) in dehydrated N,N-dimethylformamide (10 mL) at 0 C and the mixture was left to stand overnight. The reaction mixture was poured into saturated aqueous sodium hydrocarbonate and the whole was extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate 1:1 v/v) to afford 364 mg (70%) of the title compoundas a white solid. 1H NMR (400 MHz, CDCl3) delta 8.83 (d, J = 4.8 Hz, 2H), 8.50 (d, J = 8.4 Hz, 2H), 7.88 (d, J = 8.4 Hz, 2H), 7.36(dd, J = 7.2, 1.6 Hz, 1H), 7.27 (ddd, J = 8.0, 8.0, 1.8 Hz, 1H), 7.23 (t, J = 4.8 Hz, 1H), 6.94 (ddd, J 7.6, 7.6, 0.8 Hz, 1H), 6.90 (d, J = 8.4 Hz,1H), 6.80 (t, J = 5.8 Hz, 1H), 4.69 (d, J = 5.6 Hz, 2H), 4.01 (t, J = 6.6 Hz,2H), 1.91 – 1.82 (m, 2H), 1.07 (t, J = 7.4 Hz, 3H).

According to the analysis of related databases, 199678-12-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Ohashi, Masao; Gamo, Kanae; Tanaka, Yuta; Waki, Minoru; Beniyama, Yoko; Matsuno, Kenji; Wada, Jun; Tenta, Masafumi; Eguchi, Jun; Makishima, Makoto; Matsuura, Nobuyasu; Oyama, Takuji; Miyachi, Hiroyuki; European Journal of Medicinal Chemistry; vol. 90; (2015); p. 53 – 67;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia