Day: May 18, 2021

Reference of 84905-80-6, 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.84905-80-6, name is 4-Chloro-5H-pyrrolo[3,2-d]pyrimidine, molecular formula is C6H4ClN3, molecular weight is 153.57, as common compound, the synthetic route is as follows.

(i) Production of {4-[(4-chloro-5H-pyrrolo[3,2-d]pyrimidin-5-yl)methyl]phenyl}methanol 4-Chloro-5H-pyrrolo[3,2-d]pyrimidine (307 mg) was dissolved in N,N-dimethylformamide (2 mL), potassium carbonate (304 mg) was added, and the mixture was stirred at room temperature for 30 min. 4-Hydroxymethylbenzyl chloride (377 mg) was added, and the mixture was stirred at room temperature for 16 hrs. After diluting with water (30 mL), the mixture was extracted with ethyl acetate/tetrahydrofuran (3:1, 80 mL*2). The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was separated and purified by silica gel column chromatography (eluent, hexane:ethyl acetate=80:20 ? 0:100) to give the title compound (383 mg) as a powder. 1H-NMR(CDCl3) delta: 2.15 (1H, br s), 4.69 (2H, d, J= 4 Hz), 5.71 (2H, s), 6.76 (1H, m), 7.06 (2H, d, J= 8 Hz), 7.34 (2H, d, J= 8 Hz), 7.50 (1H, d, J= 3 Hz), 8.69 (1H, s).

Statistics shows that 84905-80-6 is playing an increasingly important role. we look forward to future research findings about 4-Chloro-5H-pyrrolo[3,2-d]pyrimidine.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP1752457; (2007); 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 59549-51-8, name is 5-Bromo-2-chloro-4-(methylthio)pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Formula: C5H4BrClN2S

To5-bromo-2-chloro-4-(methylthio)pyrimidine (3 g, 12.53 mmol) in dioxane (12.53 mL) was added 2-methylpropan-2-amine (7.93 mL, 75 mmol). The mixture was stirred at 100 C overnight in a sealed vessel. The solvent was removed under reduced pressure and the residue was dissolved in 100 mL ethyl acetate and washed with 50 mL of a 1M aqueous solution of sodium hydrogen phosphate. The aqueous layer was back-extracted with 50 mL ethyl acetate. The combined organic layers were dried over anhydrous magnesium sulfate, filtered and concentrated to give 5-bromo-N-tert-butyl-4-(methylthio)pyrimidin-2- amine (3.4 g, 12.31 mmol, 98% yield) as a solid. 1H NMR (400 MHz, DMSO-d6) delta ppm 8.61 – 8.72 (m, 1 H), 8.08 (s, 1 H), 6.95 – 7.17 (m, 1 H), 2.48 (s, 2 H), 1.38 (s, 9 H).MS (ESI) m/z 276.0 [M+l]+ and 278.2 [M+l]+.

With the rapid development of chemical substances, we look forward to future research findings about 59549-51-8.

Reference:
Patent; SIGNAL PHARMACEUTICALS, LLC; BENNETT, Brydon, L.; ELSNER, Jan; ERDMAN, Paul; HILGRAF, Robert; LEBRUN, Laurie, Ann; MCCARRICK, Meg; MOGHADDAM, Mehran, F.; NAGY, Mark, A.; NORRIS, Stephen; PAISNER, David, A.; SLOSS, Marianne; ROMANOW, William, J.; SATOH, Yoshitaka; TIKHE, Jayashree; YOON, Won, Hyung; DELGADO, Mercedes; WO2012/145569; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 22536-61-4, 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.22536-61-4, name is 2-Chloro-5-methylpyrimidine, molecular formula is C5H5ClN2, molecular weight is 128.56, as common compound, the synthetic route is as follows.

NBS (0.28g, 1.56mmol) and AIBN (0.05g, 0.31mmol) were added to a solution of Example 52C (0.2g, 1.56mmol)in carbon tetrachloride (10mL) and the mixture was stirred at 80C for 12 hours. Water was added and the aqueouslayer was extracted with dichloromethane. The organic layer was purified by preparative TLC (ethyl acetate) to give thetitle compound (40mg), LCMS (ESI) m/z: 206 [M+1]+.

Statistics shows that 22536-61-4 is playing an increasingly important role. we look forward to future research findings about 2-Chloro-5-methylpyrimidine.

Reference:
Patent; Harbin Zhenbao Pharmaceutical Co., Ltd.; Medshine Discovery Inc.; CHEN, Shuhui; CHEN, Zhengxia; DAI, Meibi; XIE, Cheng; LI, Peng; ZHANG, Yang; LIANG, Guibai; WANG, Qiang; LIAO, Jiangpeng; SUN, Fei; HU, Guoping; LI, Jian; (166 pag.)EP3333157; (2018); 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.51940-64-8, name is Ethyl 2,4-Dichloro-5-pyrimidinecarboxylate, molecular formula is C7H6Cl2N2O2, molecular weight is 221.0407, as common compound, the synthetic route is as follows.Computed Properties of C7H6Cl2N2O2

Ethyl 2-chloro-4-(4-chloro-3-methoxyphenylamino)pyrimidine-5-carboxylate (RJ1- 061): A mixture of ethyl 2,4-dichloropyrimidine-5-carboxylate (0.442 g, 2.0 mmol), 4-chloro-3- methoxyaniline (0.331 g, 2.1 mmol), DIPEA (0.42 mL, 2.4 mmol), and iPrOH (2 mL) was added to a 5 mL microwave vial which was then sealed and placed in a hot oil bath with stirring at 85 C overnight for 17 hours. At this point, a brown solid had formed and this was then washed with iPrOH (10 mL), water (10 mL), iPrOH (10 mL), and hexanes (10 mL) to yield RJ1-061 as a brown solid (0.570 g, 83%). m.p. = 119 C (decomposed). XH NMR (400 MHz, DMSO-) delta 10.27 (s, 1H), 8.81 (s, 1H), 7.48 (d, J= 2.3 Hz, 1H), 7.43 (d, J= 8.6 Hz, 1H), 7.28 (dd, J= 8.6, 2.3 Hz, 1H), 4.37 (q, J= 7.1 Hz, 2H), 3.85 (s, 3H), 1.34 (t, J= 7.1 Hz, 3H). LRMS (ESI+) m/z 342.1 (MC135C135+H)+, 344.0 (MC135C137+H)+, 346.0 (MC137C137+H)+; (ESI-) m/z 339.3 (MC135C135-H)-; HRMS (ESI+) m/z calculated for C14H13CI2N3O3 (M+H)+ 342.04067, found 342.04100.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,51940-64-8, Ethyl 2,4-Dichloro-5-pyrimidinecarboxylate, and friends who are interested can also refer to it.

Reference:
Patent; H. LEE MOFFITT CANCER CENTER AND RESEARCH INSTITUTE, INC.; SCHOeNBRUNN, Ernst; LAWRENCE, Nicholas, J.; LAWRENCE, Harshani, R.; (257 pag.)WO2016/22460; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 20090-58-8, Adding some certain compound to certain chemical reactions, such as: 20090-58-8, name is 4-Chloro-5-methylpyrimidin-2-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 20090-58-8.

A solution of 4-chloro-5-methylpyrimidin-2-amine (30 mg, 0.20 mmol) in ethanol (0.5 ml) was treated with triethylamine (0.058 ml, 0.41 mmol) and 2,2-dimethyl-3- (methylamino)propan-l-ol (36.7 mg, 0.31 mmol) and the mixture was irradiated in a microwave reactor at 150C for 3.5 h, then quenched with 6N HCl (0.070 ml, 0.41 mmol) and the residue was purified by mass-triggered preparative HPLC (Mobile phase: A = 0.1% TFA/H2O, B = 0.1% TFA/MeCN; Gradient: B = 0 – 30%; 12 min; Column: CI 8) to give 3-((2-amino-5- methylpyrimidin-4-yl)(methyl)amino)-2,2-dimethylpropan-l-ol 2,2,2-trifluoroacetate (6 mg, 0.018 mmol, 8% yield) as a white solid. MS (ES+) C11H20N4O requires: 224, found: 225 [M+H]+. NMR (600 MHz, de-DMSO) delta: 11.95 (brs, 1H), 7.57 (s, 1H), 7.47 (brs, 2H), 4.65 (brs, 1H), 3.71 (brs, 2H), 3.35 (s, 3H), 3.16 (s, 2H), 2.22 (s, 3H), 0.83 (s, 6H).

According to the analysis of related databases, 20090-58-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOARD OF REGENTS, UNIVERSITY OF TEXAS SYSTEM; LEWIS, Richard, Thomas; JONES, Philip; PETROCCHI, Alessia; REYNA, Naphtali; HAMILTON, Matthew, Michael; LEO, Elisabetta; (74 pag.)WO2016/145383; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 4316-93-2, 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 4316-93-2, name is 4,6-Dichloro-5-nitropyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

6-Chloro-5-nitropyrimidin-4-amine[00161] A solution of 28% aqueous ammonium hydroxide (670 mL, 5.35 mol, 1.04 equiv) was added in a drop-wise fashion to a rapidly stirred solution of the 4,6-dichloro-5- nitropyrimidine solid (1000 g, 5.16 mol, 1.00 equiv) in diethyl ether (4000 mL) and methanol (670 mL). The addition was carried out over a period of 2 hours. Upon completion of addition, the resulting yellow solid was filtered off, washed with water and hexane, and dried under reduced pressure to give the title compound as a yellow solid (yield: 675 g). This crude solid was used in the next step without any further purification. NMR (400 MHz, DMSO- d6): delta 8.97 (s, 1H), 7.91 (broad s, 2H). MS (EI) for C4H3CIN4O2: 175 (MH+).

According to the analysis of related databases, 4316-93-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; EXELIXIS, INC.; PATRICK, Kearney; WO2012/37226; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 5751-20-2 , The common heterocyclic compound, 5751-20-2, name is 2-(Methylthio)pyrimidin-4(3H)-one, molecular formula is C5H6N2OS, 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 2, Preparation of 5-bromo-2-methylthio-4-pyrimidinone: Take 142 g of 2-methylthio-4-pyrimidinone, dissolve in 500 ml of methylene chloride, add NBS 190 g, reflux for 6 hours, After the reaction is completed, cool to room temperature, filter, wash the filtrate, organicThe phase was dried and recrystallized on an ice bath to give 190 g of a pale yellow solid in a yield of 87percent.

The synthetic route of 5751-20-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Weiju Industrial Co., Ltd.; Liu Hui; (6 pag.)CN107488175; (2017); A;,
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 5305-59-9, name is 6-Chloropyrimidin-4-amine. This compound has unique chemical properties. The synthetic route is as follows. category: pyrimidines

The 400mg4-amino-6-chloro-pyrimidine, 1.51g (1.5equiv) adding cesium carbonate flask, 10mLN, N ‘-dimethyl formamide as a solvent, adding 405 mu L (1.5equiv) morpholine, heating to 100 C, reaction 12h. Adding proper amount of water, extraction with ethyl acetate, saturated salt water washing, drying by anhydrous sodium sulfate, filter, evaporate solvents under reduced pressure, the residue is purified by silica gel column chromatography separation, methanol/dichloromethane = 1/50 elution, to get the yellow solid 245 mg, yield 44%.

With the rapid development of chemical substances, we look forward to future research findings about 5305-59-9.

Reference:
Patent; East China University of Technology; Mao, Fei; Wang, Huan; Li, Xiaokang; Zhang, Haiyan; Lu, Zhengyu; Li, Jian; (43 pag.)CN105418592; (2016); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 1060816-58-1, Adding some certain compound to certain chemical reactions, such as: 1060816-58-1, name is 5-Bromo-2-chloro-7H-pyrrolo[2,3-d]pyrimidine,molecular formula is C6H3BrClN3, 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 1060816-58-1.

To a stirred solution of 5-bromo-2-chloro-7H-pyrrolo[2,3-d]pyrimidine (3.0 g, 12.9 mmol), cyclohexanol (2.59 g, 25.9 mmol) and PPh3 (8.46 g, 32.3 mmol) in THF (100 mL) was added DEAD (5.62 g, 32.3 mmol) dropwise at 0 C. The resulting solution was stirred for 16 h at room temperature under nitrogen atmosphere. The resulting solution was condensed under reduced pressure. The residue was purified by reversed phase flash chromatography with the following conditions: Column: WelFlash TM C18-I, 20-40 um, 330 g; Eluent A: Water (plus 10 mmol/L TEA); Eluent B: ACN; Gradient: 70% – 90% B in 25 min; Flow rate: 80 mL/min; Detector: UV 200/220 nm; desired fractions were collected at 78% B and concentrated under reduced pressure to afford 5-bromo-2-chloro-7-cyclohexyl-7H-pyrrolo[2,3-d]pyrimidine (1.7 g, 42%) as a white solid.1H NMR (400 MHz, DMSO-d6) d 8.84 (s, 1H), 8.11 (s, 1H), 4.67-4.49 (m, 1H), 1.96-1.64 (m, 7H), 1.47 (q, J = 13.5 Hz, 2H), 1.32-1.12 (m, 1H). LC/MS (ESI, m/z): [(M + 1)]+ = 313.95, 315.95

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. 1060816-58-1, 5-Bromo-2-chloro-7H-pyrrolo[2,3-d]pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; KYMERA THERAPEUTICS, INC.; JI, Nan; MAINOLFI, Nello; WEISS, Matthew; (977 pag.)WO2020/10210; (2020); 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. 1558-17-4, name is 4,6-Dimethylpyrimidine, the common compound, a new synthetic route is introduced below. Quality Control of 4,6-Dimethylpyrimidine

Example 24, 25 To a solution of 4,6-dimethylpyrimidine (1.08 g, 10 mmol) in THF (40 ml) was added dropwise at -78 C a solution of n-butyllithium. To the solution was added benzylbromide (1.71 g, 10 mmol). The mixture waswarmed up to 0 C and stirred for 30 minutes. To the reaction mixture was added an aqueous solution of ammonium chloride. The mixture was extracted with ethyl acetate, washed with water, dried and concentrated. The obtained residue was chromatographed on silica gel (n-hexane-ethyl acetate). The obtained fraction was concentrated to give 4-methyl-6-phenethylpyrimidine (1.7 g). Compound (I-24) and (I-25) were prepared from the above-obtained 4-methyl-6-phenethylpyrimidine in accordance with Example 2 and 3. Compound (I-24) 1H-NMR(CDCl3) delta: 1.40(3H,t,J=7.1Hz), 3.06(4H,s), 4.35(2H,q,J=7.1Hz), 6.39(1H,s), 6.86(1H,s), 7.12-7.35(6H,m), 8.95(1H,s). Compound (1-25) 1H-NMR(d6-DMSO) delta: 3.00(4H,s), 6.29(1H,s), 7.15-7.40(6H,m), 8.92(1H,s).

The synthetic route of 1558-17-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SHIONOGI & CO., LTD.; EP1219607; (2002); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia