Tag: M.W:100-200

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. 2227-98-7, name is 4-Aminopyrrolo[3,2-d]pyrimidine, molecular formula is C6H6N4, 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 2227-98-7

[0035] Example A. Synthesis of 2-[({4-amino-5H-pyrrolo[3,2-d]pyrimidin-7- yljmethyl) amino] ethan-l-ol (A.1). (0059) (0060) [0036] 2-[ ({4-Amino-5H-pyrrolo[3, 2-dJpyrimidin- 7-yl }methyl) amino] ethan-l-ol (A.1). 2-Aminoethanol (0.099 mL, 1.64 mmol), 9-deazaadenine (0.220 g, 1.64 mmol) and aq. formaldehyde solution (37%, 0.15 mL, 1.99 mmol) were stirred together in tert-butanol (3 mL) at 70 C for 16 h. Silica gel was added to absorb all the solvent then the solvent was evaporated and the residue purified by chromatography on silica gel (CHCl3-MeOH-28% aq.NH4OH, 70:25:5). Fractions containing product were evaporated and the residue chromatographed again on silica gel (2-PrOH-28% aq. NH4OH, 92:8) to give A.1 as a colourless solid (0.101 g, 30%). NMR (500 MHz, CD3OD): delta 8.16 (s, 1H), 7.47 (s, 1H), 3.95 (s, 2H), 3.68 (t, J = 5.6 Hz, 2H), 2.78 (t, J = 5.6 Hz, 2H). 13C NMR (125.7 MHz, CD3OD, centre line delta 49.0): delta 152.1 (C), 150.9 (CH), 146.6 (C), 129.0 (CH), 1 15.4 (C), 114.4 (C), 61.6 (CH2), 51.6 (CH2), 43.4 (CH2). ESI-HRMS calcd for C9H14N50+, (M+H) 208.1 193, found 208.1 192.

With the rapid development of chemical substances, we look forward to future research findings about 2227-98-7.

Reference:
Patent; ALBERT EINSTEIN COLLEGE OF MEDICINE OF YESHIVA UNIVERSITY; SCHRAMM, Vern, L.; CLINCH, Keith; GULAB, Shivali, Ashwin; WO2015/123101; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 2134-38-5, Adding some certain compound to certain chemical reactions, such as: 2134-38-5, name is Ethyl 2-methylpyrimidine-5-carboxylate,molecular formula is C8H10N2O2, 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 2134-38-5.

Step 2: Preparation of N-(4-chloro-6-(ethylamino)pyrimidin-5-yl)-2-methylpyrimidine-5- carboxamide.To a mixture of 6-chloro-N4-ethylpyrimidine-4,5 -diamine (16 g, 91 mmol) and ethyl -2- methylpyrimidine-5-carboxylate (15 g, 90 mmol) in 50 ml of dimethyl ether at RT, a slurry of sodium teri-butoxide (9.1 g, 92 mmol) in DME (25 ml) was added over the course of 1 min (reaction internal temperature rose to 43 C) . The reaction mixture was then stirred at RT for 2 h, after which it was quenched by the addition of water (75 ml) and EtOAc (75 ml). The reaction mixture was extracted with EtOAc (75 ml x 2). The aqueous layer was then charged with acetic acid (5.3 ml, 92 mmol) and a slurry formed. The solid was collected by filtration, then washed with 75 ml of 1 : 1 DME : water, after which it was dried under vacuum at 35 C for 16 h to provide N-(4-chloro-6-(ethylamino)pyrimidin-5-yl)-2- methylpyrimidine-5-carboxamide. MS (ESI) Calc’d for Ci2Hi4ClN60 [M+H]+: 293, found: 293.

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. 2134-38-5, Ethyl 2-methylpyrimidine-5-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MCGOWAN, Meredeth Ann; FONG, Kin Chiu; ANTHONY, Neville John; ZHOU, Hua; KATZ, Jason D.; YANG, Lihu; LI, Chaomin; TIAN, Yuan; MU, Changwei (Charles); YE, Baijun; SHI, Feng; ZHAO, Xiaoli; FU, Jianmin; WO2015/188369; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 1558-17-4, 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 1558-17-4 as follows.

General procedure: Irradiation procedure. The dimethylpyrazine or dimethylpyrimidine was placed in a Pyrex tube, attached to the vacuum line, and subjected to three freeze-thaw cycles. The remaining material was then allowed to vaporize into a quartz reaction flask (3 L) that had been evacuated overnight. The resulting pressure in the reaction flask ranged from 1.0 to 1.5 Torr. The flask was irradiated for 5 min. in a Rayonet reaction equipped with either 2, 4,6, 8, or 10 low-pressure 2537 A Hg lamps.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1558-17-4, its application will become more common.

Reference:
Article; Pavlik, James W.; Vongakorn, Tharinee; Kebede, Naod; Arkivoc; vol. 2017; 5; (2017); p. 216 – 228;,
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Pyrimidine – Wikipedia

Electric Literature of 22536-65-8, 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.22536-65-8, name is 2-Chloro-5-methoxypyrimidine, molecular formula is C5H5ClN2O, molecular weight is 144.56, as common compound, the synthetic route is as follows.

A suspension of 4-((4-((benzo[d][1,3]oxathiol-6-yl)-2-fluorophenoxy)methyl)piperidine (155 mg, 0.45 mmol)), 2-chloro-5-methoxypyrimidine (78 mg, 0.54 mmol) and diisopropylethylamine (87 mg, 0.68 mmol) in acetonitrile (10 mL) was stirred at reflux overnight. Upon cooling, the reaction mixture was allowed to cool to ambient temperature and the solvent was removed in vacuo and the crude product was purified by column chromatography eluting with hexanes: ethyl acetate (4: 1) to obtain the title product (63 mg, 31%) as a white powder.

The chemical industry reduces the impact on the environment during synthesis 22536-65-8, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Peu Lama Na Perm Syutikeolseu In Keu .; Man Su-reu-ta-rek-su-ha-il; Cha Pi-beu-mi-ka-il; Yu Din-mi-ka-il; Ge Jen-cheu-be-i-yu-ri; Ni Ki-tin-al-rek-san-deu-reu; (190 pag.)KR2019/15535; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 7504-94-1 , The common heterocyclic compound, 7504-94-1, name is 2-Hydrazinylpyrimidine, molecular formula is C4H6N4, 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-hydrazinopyrimidine (100 mg, 0.91 mmol) and CDI (295 mg, 1.82 mmol) in THF (2 mL) was stirred at room temperature for 18 h. The solid material was removed by filtration, washing with ethyl acetate. The solid residue was purified by Biotage Isolera chromatography (silica gel, eluting with 0-20% MeOH in DCM) to give 20 mg (16% yield) of the title compound as a yellow solid.1H NMR (250 MHz, DMSO-d6) d 12.59 (s, 1H), 8.50 (dd, J = 2.0, 3.8 Hz, 1H), 8.28 (dd, J = 2.0, 7.0 Hz, 1H), 6.66 (dd, J = 3.8, 7.0 Hz, 1H). LCMS (Analytical Method E) Rt= 0.30 min, MS (ESIpos): m/z= 137.1 [M+H]+.

The synthetic route of 7504-94-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BLACKTHORN THERAPEUTICS, INC.; JONES, Robert M.; BRANDT, Gary; (506 pag.)WO2020/97609; (2020); 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 5466-43-3, name is 2,4-Dichloro-6,7-dihydro-5H-cyclopenta[d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 2,4-Dichloro-6,7-dihydro-5H-cyclopenta[d]pyrimidine

Reference Example 60 (R)-1-(2-chloro-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)-N-methylpiperidine-3-carboxamide Diisopropylethylamine (3.7 ml, 21.2 mmol) was added into chloroform (25 ml) solution of 2,4-dichloro-6,7-dihydro-5H-cyclopenta[d]pyrimidine (1 g, 5.29 mmol) prepared in Step 3 of Reference Example 52 and (R)-(-)-3-piperidincarboxylic acid (0.75 g, 5.82 mmol), and they were stirred at 70 C. overnight. After cooing the reaction solution to room temperature, methylamine hydrochloride (0.36 g, 5.29 mmol), N-(3-dimethylaminopropyl)-N’-ethylcarbodiimide hydrochloride (1.1 g, 5.82 mmol) and 1-hydroxybenzotriazole hydrate (0.79 g, 5.82 mmol) were added thereto, and they were stirred at room temperature overnight. The reaction solution was diluted with dichloromethane, washed with water, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was crystallized by using ethyl acetate to give the titled compound (1.1 g) as a white solid. 1H NMR (400 MHz, CDCl3) delta 6.31 (brs, 1H), 4.21 (d, 1H), 4.07 (d, 1H), 3.60 (t, 1H), 3.30 (t, 1H), 2.97 (t, 2H), 2.95-2.75 (m, 5H), 2.42 (brs, 1H), 2.15-2.00 (m, 3H), 2.00-1.90 (m, 1H), 1.80-1.70 (m, 1H), 1.55 (d, 1H).

With the rapid development of chemical substances, we look forward to future research findings about 5466-43-3.

Reference:
Patent; YUHAN CORPORATION; SIM, Jae Young; CHA, Myung; KIM, Tae Kyun; YOON, Young Ae; KIM, Dong Hoon; (59 pag.)US2016/90374; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 874-14-6, 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. 874-14-6, name is 1,3-Dimethyluracil, molecular formula is C6H8N2O2, 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.

A mixture of A-5 (8.00 g, 96.28 mmol), 1,3-dimethylpyrimidine-2,4-dione (13.49 g, 96.28 mmol) and EtONa (32.76 g, 481.40 mmol) in EtOH (150 mL) was stirred at 80 °C for 5 hours. The solid was collected by filtration, washed with EtOH (50 mL), and dried in an oven to afford A-6 (12.50 g, 92.51 mmol) as a solid. 1H NMR (400MHz, DMSO-d6) delta 11 7.97 (d, 1H), 7.43 (d, 1H), 5.62 (d, 1H), 5.35 (d, 1H).

According to the analysis of related databases, 874-14-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PRAXIS PRECISION MEDICINES, INC.; REDDY, Kiran; MARTINEZ BOTELLA, Gabriel; GRIFFIN, Andrew Mark; MARRON, Brian Edward; (168 pag.)WO2018/98500; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 74840-47-4, 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 74840-47-4, name is 5-Chloro-2-methylpyrimidine-4-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows.

A 4 mL Wheaton scintillation vial was charged with 280 pL of a 0.6 mlvi solution of 5- chloro-2-methylpyrimidine-4-carboxylic acid in N,N-dimethylacetamide (30.0 mg, 1.2 equivalents, 0.2 mmol), a 500 pL solution of 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5- b]pyridinium 3-oxid hexafluorophosphate in N,N-dimethylacetamide (58.5 mg, 1.1 equivalents, 0.15 mmol, HATU), a 500 pL solution of methyl 5-[(3-phenylpropyl)amino]pentanoate hydrochloride in N,N-dimethylacetamide (40.0 mg, 0.14 mmol, Example 149-Step 2), neat triethylamine (58.9 pL, 3 equivalents, 0.42 mmol), and a stir bar. This was capped with a white seal and microwave cap for an Anton Paar microwave reactor. The vial was heated in an Anton Paar Synthos 3000 parallel microwave optimizer for 15 minutes at 120 C. Upon completion, the reaction mixture was filtered, and the filtrate was concentrated to dryness under reduced pressure. The residue was then dissolved in 1000 pL of dioxane. To this, 1000 pL of a 1 M LiOH aqueous solution in 75% CH3OH was added. The mixture was then heated at 60 C for 1 hour. The reaction mixture was then filtered once more and concentrated under reduced pressure. The residue was re-dissolved in dimethyl sulfoxide/methanol and purified using preparative-HPLC to give the titled compound (42.3 mg, 73.6%). ?H NMR (400 MHz, DMSO-d6) ppm 8.72 (d, J = 35.5 Hz, 1H), 7.31 -7.08 (m, 4H), 6.97(a, J = 7.4 Hz, 1H), 3.52 – 3.41 (m, 2H), 3.09 – 3.05 (m, 1H), 2.66 (t, J = 7.6 Hz, 1H), 2.59 (a, J =23.0 Hz, 3H), 2.43 (t, J = 7.3 Hz, 1H), 2.26 (t, J = 6.9 Hz, 1H), 2.06 (t, J = 7.2 Hz, 1H), 1.94 (p, J =7.5, 6.9 Hz, 1H), 1.80 (dt, J = 13.0, 6.2 Hz, 2H), 1.70- 1.56 (m, 3H), 1.50 (q, J = 8.2, 7.8 Hz, 1H),1.35 (p, J = 6.8 Hz, 1H); MS (APCf) m/z 390.0 (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 74840-47-4, 5-Chloro-2-methylpyrimidine-4-carboxylic acid.

Reference:
Patent; ABBVIE INC.; BLACK, Lawrence, A.; BUNNELLE, William, H.; CHEN, Da; CLAPHAM, Bruce; DEGOEY, David, A.; DENG, Xiangjun; FU, Liqiang; HAZELWOOD, Lisa, A.; KONG, Linglong; LANG, Qingyu; LEE, Chih-Hung; LI, Mingfeng; LUNDGAARD, Greta, L.; PATEL, Meena, V.; TAO, Ruihong; ZHANG, Lin; ZHANG, Qingwei; ZHENG, Qiangang; ZHU, Wei; (289 pag.)WO2017/177004; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 213265-83-9, 4,6-Dichloro-5-fluoropyrimidine, 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, Formula: C4HCl2FN2, blongs to pyrimidines compound. Formula: C4HCl2FN2

Stage 3 (0508) 4,6-Dichloro-5-fluoro-pyrimidine (1 eq), 3,4-dichlorophenyl boronic acid (0.7 eq) and Pd(PPh3)4 (0.05 eq) were suspended in 1,4-dioxane (20 vol). A 2M K2CO3 solution (6.75 vol) was added and the reaction mixture was heated at 90 C. with stirring for 2 hours under an atmosphere of N2. The reaction mixture was cooled to room temperature and concentrated in vacuo. The residue was dissolved in EtOAc and water. The mixture was partitioned and the aqueous layer further extracted with EtOAc. The combined organic layers were washed with saturated aqueous NaCl, dried over Na2SO4, filtered and the solvent removed in vacuo. The resulting residue was purified by flash column chromatography (eluent: [1:15] EtOAc:heptane) to afford the required target compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,213265-83-9, 4,6-Dichloro-5-fluoropyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; CHDI FOUNDATION, INC.; Wityak, John; Toledo-Sherman, Leticia M.; Dominguez, Celia; Courtney, Stephen Martin; Yarnold, Christopher John; De Aguiar Pena, Paula C.; Scheel, Andreas; Winkler, Dirk; US9145373; (2015); B2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 5305-59-9, 6-Chloropyrimidin-4-amine, 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, 5305-59-9, blongs to pyrimidines compound. category: pyrimidines

Add in the reaction flask4-amino-6-chloropyrimidine (6 g, 46.5 mmol),Tetrahydrofuran (75 mL) and pyridine (9.0 mL).Cyclopropylcarbonyl chloride (5.3 g, 50.7 mmol) was added dropwise at room temperature.10 minutes after the drop finished,The reaction solution was heated to 60 C,The reaction was incubated for 3 hours.After the reaction solution was cooled,Diluted with water (100 mL)Ethyl acetate was extracted twice,The organic phase was combined and used1N hydrochloric acid and saturated brine and dried.After concentration,Heated with n-hexane,To give N- (6-chloropyrimidin-4-yl)Cyclopropylcarboxamide(Pale yellow solid, 4.2 g, 45.8%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5305-59-9, its application will become more common.

Reference:
Patent; Zhang, Ruihao; (36 pag.)CN105949178; (2016); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia