Category: pyrimidines

Related Products of 16097-60-2, 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. 16097-60-2, name is 2-Amino-4-chloro-6-(trifluoromethyl)pyrimidine. A new synthetic method of this compound is introduced below.

Under an ice bath, add 2-amino-4-chloro-6-trifluoromethylpyrimidine (197.0 mg, 1.0 mmol), N-tert-butoxycarbonyl-1,3-propanediamine (208.8 mg, 1.2 mmol) , Dissolved in methanol (8.0 ml), and stirred at reflux overnight. The solvent was recovered under reduced pressure to obtain a residue, which was purified by silica gel column chromatography. PE: EA (5: 1-2: 1) was first used as eluent to obtain 1-36 as a white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,16097-60-2, 2-Amino-4-chloro-6-(trifluoromethyl)pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Zhejiang University; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Liu Tao; Li Jia; Dong Xiaowu; Zhou Yubo; Hu Yongzhou; Wang Peipei; Jin Tingting; Liu Jieyu; Hu Xiaobei; (51 pag.)CN110872277; (2020); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 886365-79-3 , The common heterocyclic compound, 886365-79-3, name is 5-Bromo-2-(2-methoxyethylamino)pyrimidine, molecular formula is C7H10BrN3O, 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.

Synthesis of 4-(4-{2-[(2-methoxyethyl)amino]pyrimidin-5-yl}phenyl)-N- [5-(2-methyl-l,3-thiazol-4-yl)pyridin-2-yl]tetrahydro-2H-pyran-4-carboxamide (example 207)To a solution of 1-105 (75 mg, 0.16 mmol), KOAc (157 mg, 1.6 mmol),PdCi2(dppf).CH2Ci2 (33 mg, 0.04 mmol) in dioxane (2.0 mL) at room temperature is added R-8 (115 mg, 0.46 mmol). The reaction mixture is heated at 100 C in a sealed tube for 16 hours. The reaction mixture is allowed to cool to room temperature, followed by the addition R-31 (88 mg, 0.38 mmol) in THF (2.0 mL), 20% Na2C03 solution (2.0 mL), and Pd(PPh3)4 (23 mg, 0.20 mmol). The reaction mixture is heated in the microwave at 120 C for 60 minutes, allowed to cool to room temperature, and partitioned between EtOAc and H20. The combined organics are washed with H20, dried with Na2S04, filtered, and concentrated in vacuo. The residue is purified by flash chromatography (Si02, 0-10% MeOH in EtOAc) to give the title compound 207 (36 mg).

The synthetic route of 886365-79-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BERRY, Angela; CHEN, Zhidong; DE LOMBAERT, Stephane; EMMANUEL, Michel Jose; LOKE, Pui Leng; MAN, Chuk Chui; MORWICK, Tina Marie; TAKAHASHI, Hidenori; WO2012/82817; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 99420-75-4, 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. 99420-75-4, name is 5-Methylpyrimidine-2-carboxylic acid, molecular formula is C6H6N2O2, 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.

(0648) To a solution of 5-methylpyrimidine-2-carboxylic acid (1 g, 7.24 mmol) in DMF (72.4 mL) was added Nu,Omicron-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 23 C overnight. LCMS indicated complete conversion to product. The mixture was then diluted with water, extracted with CHC13:IPA (3: 1) and washed with brine and a saturated aqueous NaHCC solution. The mixture was dried over Na2S04 concentrated in vacuo, and purified by silica gelchromatograph (0-100% Heptane:EtOAc) to yield Example 57.11 (0.7 g, 3.86 mmol, 53 % 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 -ESI (pos.) m/z: 182.2 (M+H)+

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 99420-75-4, 5-Methylpyrimidine-2-carboxylic acid.

Reference:
Patent; AMGEN INC.; DRANSFIELD, Paul John; HARVEY, James S.; MA, Zhihua; SHARMA, Ankit; (281 pag.)WO2019/89335; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 1189973-29-2, 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 1189973-29-2, name is (1-(5-Bromopyrimidin-2-yl)piperidin-3-yl)methanol. This compound has unique chemical properties. The synthetic route is as follows.

Step 2: Synthesis of {l-[5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)pyrimidin-2- yl]piperidin-3-yl}methanol :; To a solution of [l-(5-bromopyrimidin-2-yl)piperidin-3-yl]methanol (0.5 g, 1.83 mmol) in 1,4 dioxane (25 mL) were added bispinacolatodiborane (0.46 g, 3.3 mmol), potassium acetate ( 0.53 g, 5.4 mmol) and Pd (dppf)Cl2 (0.14 g, 0.18 mmol) under argon at room temperature (~25 0C). The mixture was heated at 80-90 0C for about 6 hours. It was cooled to room temperature (-25 0C), concentrated under reduced pressure and then purified through filtering column using sintered funnel full of 230-400 mesh size silica gel. It was eluted with 50% ethyl acetate in hexane and concentrated to afford title compound (0.4 g). MS m/e 289.93 (MH+).

According to the analysis of related databases, 1189973-29-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; RANBAXY LABORATORIES LIMITED; WO2009/156966; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 29939-37-5, 4-Hydroxy-6-hydrazinylpyrimidine, 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 29939-37-5, blongs to pyrimidines compound. Product Details of 29939-37-5

PREPARATION 3phenylmethyl 4-chloro-1 ,5,7,8-tetrahydro-6/-/-pyrido[3′,4′:4,5]pyrrolo[2,3-c/]pyricarboxylateStep 1 . phenylmethyl 4-[(6-oxo-1 ,6-dihydro-4-pyrimidinyl)hydrazono]-1- piperidinecarboxylateA suspension of 6-hydrazino-4(1 H)-pyrimidinone (0.966 g, 7.66 mmol) in ethanol(20 mL) and phenylmethyl 4-oxo-1 -piperidinecarboxylate (2.68 g, 1 1 .49 mmol) were heated in a 76 C oil bath for 3 hours. The reaction mixture was cooled in an ice-water bath before the solids were collected by filtration and dried under high vacuum over night to afford phenylmethyl 4-[(6-oxo-1 ,6-dihydro-4-pyrimidinyl)hydrazono]-1- piperidinecarboxylate (1 .53 g, 58%) as white solid MS (m/z) 342.1 (M+H)+

At the same time, in my other blogs, there are other synthetic methods of this type of compound,29939-37-5, 4-Hydroxy-6-hydrazinylpyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; GLAXOSMITHKLINE LLC; HAMMOND, Marlys; ZHAO, Yongdong; WO2011/56739; (2011); 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.1211522-68-7, name is 4,6-Dichloro-3-methyl-1H-pyrazolo[3,4-d]pyrimidine, molecular formula is C6H4Cl2N4, molecular weight is 203.0288, as common compound, the synthetic route is as follows.Quality Control of 4,6-Dichloro-3-methyl-1H-pyrazolo[3,4-d]pyrimidine

To a solution of 2,4-dichloropyrrolo[1,2-f][1,2,4]triazine (4a) (0.5 g, 2.7 mmol) in 2-Propanol (6 mL) was added (S)-pyrrolidin-2-ylmethanol (0.39 mL, 4.0 mmol), DIPEA (1.39 mL, 8.0 mmol) and heated at 90 C for 1 hr. The reaction was cooled to room temperature and solid obtained was collected by filtration to afford (S)-(l-(2-chloropyrrolo[2,l-f][l,2,4]triazin-4- yl)pyrrolidin-2-yl)methanol (96a) (0.49 g, 73 % yield) as a white solid; NMR (300 MHz, DMSO-i/e): delta 7.70 (dd, J= 2.6, 1.4 Hz, 1H), 6.97 (dd, J= 4.7, 1.6 Hz, 1H), 6.80 – 6.57 (m, 1H), 5.15 (t, J = 5.7 Hz, 1H, D2O exchangeable), 4.87 (t, J= 5.7 Hz, 1H), 4.44 (d, J= 17.8 Hz, 1H), 4.05 – 3.82 (m, 1H), 3.72 – 3.39 (m, 2H), 2.22 – 1.84 (m, 4H). MS (ES+): 253.3, 255.3 (M+2); MS (ES-): 287.2, 289.2 (M+Cl).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1211522-68-7, 4,6-Dichloro-3-methyl-1H-pyrazolo[3,4-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; BIOCRYST PHARMACEUTICALS, INC.; KOTIAN, Pravin, L.; BABU, Yarlagadda, S.; KUMAR, V., Satish; ZHANG, Weihe; LU, Peng-Cheng; RAMAN, Krishnan; (747 pag.)WO2018/232094; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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 85989-61-3, name is 5,7-Dichloroimidazo[1,2-c]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 85989-61-3

Example 17A; N6-{2-[7-Chloroimidazo[1,2-c]pyrimidin-5-yl)amino]ethyl}-3-nitropyridine-2,6-diamine 800 mg (4.13 mmol) of 5,7-dichloroimidazo[1,2-c]pyrimidine (Example 11A) are suspended in 20 ml of DMSO, and 1.62 g (4.54 mmol) of N6-(2-aminoethyl)-3-nitropyridine-2,6-diamine trifluoroacetate (Example 15A) and 1.6 g (12.38 mmol) of DIPEA are added. The mixture is heated at 120 C. for 16 h. After this time, water is added, and the precipitate which has separated out is filtered off with suction. It is washed with a little 2-propanol/water and the resulting solid is dried under high vacuum. 1.34 g (92% of theory) of the product are obtained as a solid.LCMS (method 7): Rt=1.44 min. (m/z=349 (M+H)+)1H-NMR (400 MHz, DMSO-d6): delta=8.29 (t, 1H), 8.15 (s, br, 1H), 8.09 (t, 1H), 7.95 (s, 1H), 7.93 (s, 1H), 7.69 (s, br, 1H), 7.50 (d, 1H), 6.92 (s, 1H), 5.92 (d, 1H), 3.67 (m, 4H).

With the rapid development of chemical substances, we look forward to future research findings about 85989-61-3.

Reference:
Patent; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; US2010/113441; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 14001-69-5, Adding some certain compound to certain chemical reactions, such as: 14001-69-5, name is 2-Methoxy-5-nitropyrimidine,molecular formula is C5H5N3O3, 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 14001-69-5.

Under 2 atmosphere, a suspension of 2-methoxy-5-nitropyrimidine (180 mg, 1.16 mmol, 1.00 equiv) and 5% Rh/C (13.8 mg, 0.60 moll Rh) in THF (11.6 mL, 0.100 M) was stirred at 23 C. Hydrazine monohydrate (69.7 mg, 1.39 mmol, 1.20 equiv) was added dropwise. The reaction 15 mixture was stirred at 23 C for 20 min. NaHCC>3 (117 mg, 1.39 mmol, 1.20 equiv) was added, followed by dropwise addition of a solution of acetyl chloride (109 mg, 1.39 mmol, 1.20 equiv) in THF (11.6 mL, 0.120 M) . The reaction mixture was stirred at 23 C for 30 min and then filtered through a short pad of celite. The celite was washed 20 with EtOAc. The combined organic solution was concentrated in vacuo. . The residue was purified by chromatography on silica gel, eluting with hexanes : EtOAc (2:1 to 0:1 (v/v)), to afford the title compound as a gray gum (125 mg, 0.682 mmol, 59% yield). Rf = 0.33 (EtOAc). NMR Spectroscopy: NMR (700 MHz, (CD3)2SO, 25 C, delta) : 10.93 (br. s, 1H) , 25 8.81 (s, 2H) , 3.91 (s, 3H) , 2.22 (br. s., 3H) . 13C NMR (175 MHz, (CD3)2SO, 25 C, delta) : 170.7, 161.8, 151.0, 131.8, 54.9, 21.6. Mass Spectrometry: HRMS (ESI-TOF) (m/z): calcd for C7H10N3O3 ( [M + H] + ), 184.0717, found, 184.0718.

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. 14001-69-5, 2-Methoxy-5-nitropyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE RESEARCH FOUNDATION FOR THE STATE UNIVERSITY OF NEW YORK; NGAI, Ming-Yu; HOJCZYK, Katarzyna, N.; (214 pag.)WO2016/57931; (2016); 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. 55405-67-9, name is 3-Bromopyrazolo[1,5-a]pyrimidine, molecular formula is C6H4BrN3, 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. Product Details of 55405-67-9

PREPARATION 107 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazolo[1,5-a]pyrimidine [Show Image] A mixture of 3-bromopyrazolo[1,5-a]pyrimidine (1.00 g, 5.1 mmol), potassium acetate (1.78 g, 18.1 mmol) and bis(pinacolato)diboron (5.77 g, 22.7 mmol) in 1,4-dioxane (20 mL) contained in a Schlenck vessel was submitted to three vacuum-argon cycles and bis(triphenylphosphine)palladium(II) dichloride (0.180 g, 0.26 mmol) was then added. The mixture was further submitted to three vacuum-argon cycles, sealed and then was stirred and heated to 100 C. After 20 hours, the reaction mixture was cooled, evaporated and then taken up in pentane and filtered through diatomaceous earth (Celite) and the filter cake was washed with a mixture of ethyl acetate/ether (3:2). The combined filtrate and washings were evaporated and the residue was stirred with n-pentane (15 mL) at -40 C for 30 minutes. The solid was filtered, washed with cold pentane and dried in vacuo to give the title compound (1.66 g, >100%) as a solid which was used without further purification. LRMS (m/z): 246 (M+1)+.1H NMR (300 MHz, CDCl3) delta ppm 1.26 (s, 12H), 6.89 (dd, 1H), 8.44 (s, 1H), 8.63 – 8.83 (m, 2H).

With the rapid development of chemical substances, we look forward to future research findings about 55405-67-9.

Reference:
Patent; Almirall, S.A.; EP2397482; (2011); 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.313339-35-4, name is 4,6-Dichloro-2-(methylthio)pyrimidine-5-carboxylic acid, molecular formula is C6H4Cl2N2O2S, molecular weight is 239.08, as common compound, the synthetic route is as follows.name: 4,6-Dichloro-2-(methylthio)pyrimidine-5-carboxylic acid

Thionyl chloride (1.6 mL, 22.1 mmol) and DMF (0.025 mL) were added to 4,6-dichloro-2-(methylthio)-pyrimidine-5-carboxylic acid (528 mg, 2.21 mmol) obtained in Reference Example 4, and the mixture was stirred at 90C for 4 hours. The mixture was concentrated under reduced pressure, and the residue was dried for 12 hours under reduced pressure. The resulting residue was dissolved in dichloromethane (11 mL), and the mixture was stirred at -78C for 30 minutes after triethylamine (0.25 mL, 1.76 mmol), and a dichloromethane (11 mL) solution of the (S)-2-(aminomethyl)pyrrolidine-1-carboxylic acid tert-butyl ester (295 mg, 1.47 mmol) obtained in Reference Example 6 were added at -78C. Thereafter, a saturated aqueous ammonium chloride solution and ethyl acetate were added to separate the organic layer. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give (S)-N-[(1-tert-butoxycarbonylpyrrolidin-2-yl)methyl]-4,6-dichloro-2-methylthiopyrimidine-5-carboxylic acid amide (538 mg, 87%). ESI-MS: m/z 421 [M + H]+. 1H-NMR (CDCl3) delta(ppm): 1.43 (s, 9H), 1.70-2.00 (m, 3H), 2.08 (m, 1H), 2.58 (s, 3H), 3.32-3.46 (m, 3H), 3.60 (m, 1H), 4.10 (m, 1H), 8.24 (brs, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,313339-35-4, 4,6-Dichloro-2-(methylthio)pyrimidine-5-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; Kyowa Hakko Kirin Co., Ltd.; EP2163554; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia