Tag: M.W:100-200

Electric Literature of 108-53-2 ,Some common heterocyclic compound, 108-53-2, molecular formula is C4H5N3O, 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.

General procedure: To a 100 ml RBF, compound 6a (10 mmol), heterocyclic amine (2.18 g, 10 mmol) and TBTU (3.21 g, 10 mmol) and dry CH2Cl2 (15 ml) were taken and the contents of the flask were cooled in an ice-bath. DIPEA (8.9 ml, 50 mmol) was added drop wise to the flask over a 1-hr period. The reaction mixture became clear after complete addition. The ice-bath was removed and the reaction mixture was stirred at room temperature for 48 hrs. The white solid (precipitated out of the reaction mixture) was filtered and washed with water (20 ml). The crude products were directly recrystallised from boiling 1,4-dioxane.

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. 108-53-2, 2-Aminopyrimidin-4(1H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Agrawal, Madhavi; Kharkar, Prashant; Moghe, Sonali; Mahajan, Tushar; Deka, Vaishali; Thakkar, Chandni; Nair, Amrutha; Mehta, Chirag; Bose, Julie; Kulkarni-Almeida, Asha; Bhedi, Dilip; Vishwakarma, Ram A.; Bioorganic and Medicinal Chemistry Letters; vol. 23; 20; (2013); p. 5740 – 5743;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 17180-94-8, 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. 17180-94-8, name is 5-Chloropyrimidine. A new synthetic method of this compound is introduced below.

General procedure: To a solution of the nitrile / sulfone (1.2 mmol) in THF (5 ml) at -78 oC (under an N2atmosphere) was added LiHMDS (1.2 mL of 1 M in THF, 1.2 mmol) dropwise and thereaction mixture was stirred at this temperature for 5 minutes. The heterocycle (1 mmol,1 eq.) was added at while the reaction mixture was at -78oC, the cooling bath wasremoved and the reaction mixture was stirred until the reaction was judged complete byLCMS analysis (generally 1 h). Solid KMnO4 (316 mg, 2 mmol, 2 eq.) and acetonitrile(1 ml) were added and the reaction mixture was stirred at room temperature until thereaction was judged complete by LCMS analysis (generally 4-6 h). The reaction mixturewas poured into saturated aqueous NaHCO3 and the layers separated. The aqueous layerwas then extracted with EtOAc (3x). All organics were combined, washed with water,brine, dried (Na2SO4) and evaporated to dryness. Purification by silica gel columnchromatography (12 g Isco silica cartridge) using hexanes and EtOAc gave the desiredproducts.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,17180-94-8, its application will become more common.

Reference:
Article; Anderson, Corey; Moreno, Jesus; Hadida, Sabine; Synlett; vol. 25; 5; (2014); p. 677 – 680;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 1450-86-8, Pyrimidine-4(3H)-thione, 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, Safety of Pyrimidine-4(3H)-thione, blongs to pyrimidines compound. Safety of Pyrimidine-4(3H)-thione

General procedure: To a solution of compound 1 (240 mg, 0.39mmol) in tetrahydrofuran (THF; 5ml) at 0 C were added triphenylphosphine (150 mg, 0.57 mmol), diethylazodicarboxylate (0.10ml, 0.55mmol) and benzo[d]oxazole-2-thiol (85 mg, 0.56ml) and stirred at 0 C for 1 h. The mixture was stirred at RT for 16 h. The mixture was diluted with 2N HCl (1ml)-MeOH (1ml) and then stirred at RT for 30 min and concentrated under reduced pressure. The resulting residue was dissolved by water and washed with diethyl ether. The mixture was added to NaHCO3 (150 mg), then extracted with ethyl acetate, washed with water, dried over MgSO4 and concentrated under reduced pressure. The resulting residue was purified by preparative TLC (CHCl3/CH3OH/28 % aq NH4OH=20/1/0.1) toobtain the title compound as a colorless solid (147.6mg, 71%).

The synthetic route of 1450-86-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wakiyama, Yoshinari; Kumura, Ko; Umemura, Eijiro; Ueda, Kazutaka; Masaki, Satomi; Kumura, Megumi; Fushimi, Hideki; Ajito, Keiichi; Journal of Antibiotics; vol. 69; 5; (2016); p. 368 – 380;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 4214-85-1, 2-Amino-6-methyl-5-nitro-3H-pyrimidin-4-one, 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, Recommanded Product: 2-Amino-6-methyl-5-nitro-3H-pyrimidin-4-one, blongs to pyrimidines compound. Recommanded Product: 2-Amino-6-methyl-5-nitro-3H-pyrimidin-4-one

A mixture of 58 (20 g) with dry DMF (250 ml) and DMF dimethylacetal (75 ml) was stirred at 100 C. for 24 h and then cooled.. acetone (500 ml) was added and the mixture was filtered and washed with acetone affording 10 as an orange/brown solid (26.3 g, 80%).. Recrystallization from DMF gave an orange solid with mp>300 C. (dec).. 1H NMR (d6-DMSO) delta 8.59 (s, 1H), 7.81 (d, J=12.5 Hz, 1H), 5.30 (d, J=12.5 Hz, 1H), 3.12 (s, 3H), 3.00 (s, 3H), 2.93 (s, 6H).. 13C NMR delta 168.4, 166.0, 159.2, 158.5, 149.5, 129.1, 90.6, 41.8, 35.7.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,4214-85-1, 2-Amino-6-methyl-5-nitro-3H-pyrimidin-4-one, and friends who are interested can also refer to it.

Reference:
Patent; Industrial Research Limited; Albert Einstein College of Medicine of Yesheva University; US6693193; (2004); B1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 22433-12-1, 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. 22433-12-1, name is (5-Bromopyrimidin-2-yl)methanol, molecular formula is C5H5BrN2O, 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.

EXAMPLE 51 2-(2-Pyrimidylmethylthio)ethylguanidine sulphate A mixture of 5-bromo-2-hydroxymethylpyrimidine (5.6 g.) and magnesium oxide (5.6 g.) in water/ethanol (2:1) was submitted to hydrogenolysis over 10% palladised charcoal for 0.5 hour. Filtration, concentration and ether extraction from an aqueous solution of the residue afforded 2-hydroxymethylpyrimidine (1.85 g.) as a mobile liquid. Reaction of this compound with thionyl chloride gives 2-chloromethylpyrimidine.

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 22433-12-1, (5-Bromopyrimidin-2-yl)methanol.

Reference:
Patent; Smith Kline & French Laboratories Limited; US3950333; (1976); A;,
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Pyrimidine – Wikipedia

Electric Literature of 19808-30-1, 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. 19808-30-1, name is 5-Bromopyrimidin-4(3H)-one, molecular formula is C4H3BrN2O, 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 mixture of 5-bromopyrimidin-4-ol (1-111) (40 g, 0.22 mol) in POCI3 (300 mL) was added in a dropwise manner DIPEA (29 g, 0.22 mol) at room temperature. Then the resulting mixture was heated to reflux for 3 hr. TLC (petroleum ether/EtOAc 1 :1) showed the reaction was complete. Excess POCI3 was removed through distillation under reduced pressure. The residue was poured into ice-water (300 mL) slowly with stirring. The mixture was extracted with EtOAc (2 x 300 mL), the combined organic layers were washed with water (300 mL), brine (300 mL), dried over Na2S04 and concentrated under vacuum. The residue was purified by silica gel chromatography (petroleum ether/EtOAc from 20:1 to 10:1) to give 5-bromo-4-chloropyrimidine (1-112) (25 g, 60%) as a yellow oil.

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 19808-30-1, 5-Bromopyrimidin-4(3H)-one.

Reference:
Patent; PFIZER INC.; JOHNSON, Ted William; RICHARDSON, Paul Francis; COLLINS, Michael Raymond; RICHTER, Daniel Tyler; BURKE, Benjamin Joseph; GAJIWALA, Ketan; NINKOVIC, Sacha; LINTON, Maria Angelica; LE, Phuong Thi Quy; HOFFMAN, Jacqui Elizabeth; (335 pag.)WO2016/97918; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 3551-55-1 ,Some common heterocyclic compound, 3551-55-1, molecular formula is C6H8N2O2, 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.

2,4-Dimethoxypyrimidine (1.4 g, 10 mmol) was dissolved in tetrahydrofuran (14 mL) under nitrogen. cool down to around 0 C, 1M magnesium dichloride(2,2,6,6-tetramethylpiperidine)lithium salt (11 mL, 11 mmol) was added dropwise with stirring. Stirring was continued for 2 hours, then iodine (2.79 g, 11 mmol) was added with stirring. After maintaining the low temperature reaction for 2 hours, it was naturally warmed to room temperature and stirring was continued for 6 hours. The reaction was quenched with aqueous ammonium chloride solution was poured into ethyl acetate and extracted three times were combined, washed, dried, and concentrated. After the obtained crude column chromatography, 5-iodo-2,4-dimethoxypyrimidine (2.34 g, yield: 88%) was obtained

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3551-55-1, its application will become more common.

Reference:
Patent; Fuxin Fulongbao Pharmaceutical Technology Co., Ltd.; Cai Fanping; Li Xinming; (5 pag.)CN109232385; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 63155-11-3 ,Some common heterocyclic compound, 63155-11-3, molecular formula is C8H10N2O2, 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 mixture of ethyl 2-pyrimidin-2-ylacetate (900 mg, 5.42 mmol) in THF (20 mL) was added LDA (3.25 mL, 6.5 mmol) at -78 C, then the mixture was stirred at -78 C for 2 hours. To the mixture was added iodomethane (922.46 mg, 6.5 mmol), then the mixture was stirred at -78 C to 20 C for 3 hours. The mixture was quenched with sat. NH4C1 (30 mL), then the mixture was extracted with EtOAc (50 mL x 2). The combined organic phase was washed with water (20 mL) and brine (20 mL), dried over Na2S04, filtered and concentrated to give the crude product. The crude product was purified by flash chromatography on silica gel (EtOAc in PE = 0% to 20% to 45%) to give the product (730 mg, 4.05 mmol, 75% yield) as oil. 1H NMR (CDC13, 400MHz) deltaH = 8.72 (d, 2H), 7.19 (t, 1H), 4.19 (q, 2H), 4.14 – 4.07 (m, 1H), 1.62 (d, 3H), 1.22 (t, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,63155-11-3, its application will become more common.

Reference:
Patent; PRAXIS PRECISION MEDICINES , INC.; REDDY, Kiran; MARTINEZ BOTELLA, Gabriel; GRIFFIN, Andrew, Mark; MARRON, Brian, Edward; (244 pag.)WO2018/148745; (2018); 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. 34415-10-6, name is 2-Methyl-6-oxo-1,6-dihydropyrimidine-4-carboxylic acid, the common compound, a new synthetic route is introduced below. COA of Formula: C6H6N2O3

Example 1592-Methyl-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid [(5R,7R)-2-(3,5-difluoro-phenyl)-1-oxo-2-aza-spiro[4.5]dec-7-yl]amide Example 159 was made from intermediate 36 via the process of Scheme 1, supra, as follows:To a solution of intermediate 36 (5R,7R)-7-amino-2-(3,5-difluoro-phenyl)-2-aza-spiro[4.5]decan-1-one (80 mg, 0.28 mmol), triethylamine (0.16 mL, 1.14 mmol) in DMF (2.0 mL) was added 6-hydroxy-2-methyl-pyrimidine-4-carboxylix acid (49 mg, 0.32 mmol), HOBt (51 mg, 0.38 mmol) and EDCI (73 mg, 0.38 mmol). The mixture was stirred at rt overnight. The solvent was removed with Genevac, and the resulting residue was purified with spectrometry (RP-HPLC/MS) purification system (Gradient: acetonitrile in water, 25-95% in 3.9 minutes with a cycle time of 5 min. Flow rate: 100 mL/min. Mobile phase additive: 48 mM of ammonium formate. Column: Inertsil C18, 30×50 mm, 5 um particle size) to afford 26 mg (22%) of the title compound 2-methyl-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid [(5R,7R)-2-(3,5-difluoro-phenyl)-1-oxo-2-aza-spiro[4.5]dec-7-yl]amide. 1H NMR (400 MHz, CDCl3) delta 13.0 (bs, 1H), 7.94 (d, J=8.4 Hz, 1H), 7.25-7.32 (m, 2H), 7.14 (s, 1H), 6.56-6.63 (m, 1H), 4.02-4.12 (m, 1H), 3.73-3.80 (m, 2H), 2.52 (s, 3H), 2.04-2.26 (m, 3H), 1.86-1.95 (m, 2H), 1.34-1.80 (m, 5H). ESI-MS m/z: 417 (M+H)+.

The synthetic route of 34415-10-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; H. LUNDBECK A/S; US2011/98299; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 3438-61-7, name is 5-Amino-4-methylpyrimidine. A new synthetic method of this compound is introduced below., category: pyrimidines

To a solution of the reactant (109 mg, 1.0 mmol) in toluene (1.5 mL) was added acetic anhydride (0.2 mL, 2.10 mmol), acetic acid (0.2 mL, 3.5 mmol) followed by potassium acetate (196 mg, 2.0 mmol). The mixture was heated to reflux and isopentyl nitrire (0.168 mL, 1.25 mmol) in toluene (0.3 mL) was added. After 2 hours, the mixture was poured into water (20 mL). The solution was made basic by addition of Na2C03 solid. The solution was extracted with ethyl acetate (2×50 mL) and the combined organic extracts were washed with brine (50 mL), dried over magnesium sulfate and concentrated in vacuo. The residue was purified by silica gel chromatography (eluant:petroleum ether: ethyl acetate = 1 :2) to afford product product (32 mg, 0.266 mmol, Yield=27%) as yellow solid. 1H NMR (400 MHz, d6-DMSO) 5(ppm): 13.91 (1H, br), 9.35 (1H, s), 9.04 (1H, s), 8.45 (1H, s).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 3438-61-7, 5-Amino-4-methylpyrimidine.

Reference:
Patent; SAGE THERAPEUTICS, INC.; BOTELLA, Gabriel Martinez; HARRISON, Boyd L.; ROBICHAUD, Albert Jean; SALITURO, Francesco G.; BERESIS, Richard Thomas; WO2014/169832; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia