Category: pyrimidines

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. 51953-18-5, name is Pyrimidin-4-ol. A new synthetic method of this compound is introduced below., Recommanded Product: 51953-18-5

To a stirred solution containing 20.2 g (0. 21 mol) of pyrimidin-4 (3H)-one and 170 mL of water was added 10.9 g (0.27 mol) of sodium hydroxide, followed by 53.3 g (0.21 mol) of iodide. The reaction mixture was heated at 85C for 16h, then cooled to room temperature and filtered. The filter cake was washed with water, collected, and dried under reduced pressure to give 29.7g (64%) of the TITLE COMPOUND. H-NMR (300 MHz, DMSO-d6) No. 8. 17 (s, 1H), 8.43 (s, 1H), and 12.92 (brs, 1H) ; ESIMS : 223.1 (M+H) +

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, 51953-18-5, Pyrimidin-4-ol.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2005/16914; (2005); 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.60186-89-2, name is 4-Bromo-2,6-dimethoxypyrimidine, molecular formula is C6H7BrN2O2, molecular weight is 219.036, as common compound, the synthetic route is as follows.Safety of 4-Bromo-2,6-dimethoxypyrimidine

To a solution of 4-bromo-2,6-dimethoxy-pyrimidine (6.80 g, 27.94 mmol) in THF (190 mL) and diethylether (190 mL) n-butyllithium (in hexane/THF, 2.01 g, 30.74 mmol) is added dropwise with stirring at -78 C. After 4 min ethyl trifluoroacetate (4.46 g, 30.74 mmol) in THF (50 mL) is added dropwise at -78 C. The reaction mixture is stirred for 30 min at -78 C. and then the reaction is allowed to warm to room temperature slowly and stirred over night at room temperature. To the reaction mixture 1 N HCl solution is added. The resulting mixture is extracted with EA and washed with sat. sodium chloride solution and water. The organic phase is dried over sodium sulfate, filtered and the solvent is evaporated in vacuo. The residue is purified by flash column chromatography (silica gel, PE/EA=8/2) to give the product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,60186-89-2, 4-Bromo-2,6-dimethoxypyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Boehringer Ingelheim International GmbH; EICKMEIER, Christian; GERLACH, Kai; HEINE, Niklas; WEBER, Alexander; GROSS, Ulrike; US2013/225593; (2013); A1;,
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Electric Literature of 37482-64-7, 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.37482-64-7, name is 2-Chloro-4-ethoxy-6-methylpyrimidine, molecular formula is C7H9ClN2O, molecular weight is 172.61, as common compound, the synthetic route is as follows.

EXAMPLE 11 4-Ethoxy-6-methyl-2-(1-pyrazolyl)pyrimidine In anhydrous tetrahydrofuran, 173 mg of 2-chloro-4-ethoxy-6-methylpyrimidine was substituted with 68 mg of pyrazole. The reaction mixture was treated according to the procedure of Example 5 to yield 110 mg of 4-ethoxy-6-methyl-2-(1-pyrazolyl)pyrimidine, an oily compound. NMR(CDCl3)delta: 1.40(3H,t,J=7 Hz), 2.40(3H,s), 4.50(2H,q,J=7 Hz), 6.4-6.6(2H,m), b 7.81(1H,bs), 8.28(1H,d,J=3 Hz).

The chemical industry reduces the impact on the environment during synthesis 37482-64-7, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Nissin Shokuhin Kabushiki Kaisha; US4849424; (1989); A;,
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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. 110960-73-1, name is Ethyl 4-methylpyrimidine-5-carboxylate, the common compound, a new synthetic route is introduced below. Product Details of 110960-73-1

[229] Intermediate: 53: 4-methylpyrimidine-5-carboxylic acid: Intermediate 52 (2.6 g, 15.64 mmol) dissolved in sodium hydroxide solution (1.88 g, 47 mmol in 4 ml water) and refluxed. The reaction mixture was cooled to rt and acidified with con HCl to obtain the solid. Solid that obtained was filtered and dried to obtain the title compound (1.5 g) as an yellow solid. -NMR (delta ppm, DMSO-i , 400 MHz): 13.5 (bs, 1H), 9.14 (s, 1H), 9.05 (s, 1H), 2.71 (s, 3H).

The synthetic route of 110960-73-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ICOZEN THERAPEUTICS PVT. LTD.; RHIZEN PHARMACEUTICALS S.A.; MUTHUPPALANIAPPAN, Peyyappan; VISWANADHA, Srikant; MERIKAPUDI, Gayatri, Swaroop; VAKKALANKA, Swaroop, Kumar, V.S.; WO2011/42797; (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. 43024-61-9, name is Ethyl 7-hydroxypyrazolo[1,5-a]pyrimidine-6-carboxylate. A new synthetic method of this compound is introduced below., Formula: C9H9N3O3

Ethyl 7-hydroxypyrazolo[1,5-a]pyrimidine-6-carboxylate () (3.20 g, 15.5 mmol) was dissolved in phosphorus oxychloride (30 mL), N,N-diisopropylethylamine (5.4 mL, 30.9 mmol) was added, and the mixture was stirred with heating at 100 C for 3 hr. After confirmation of consumption the starting materials, phosphorus oxychloride was evaporated under reduced pressure, and the residue was dissolved in ethyl acetate. The solution was added dropwise to a saturated aqueous sodium hydrogen carbonate solution under ice-cooling. To the saturated aqueous sodium hydrogen carbonate solution was added ethyl acetate, and the mixture was extracted 3 times. The combined organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure.

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, 43024-61-9, Ethyl 7-hydroxypyrazolo[1,5-a]pyrimidine-6-carboxylate.

Reference:
Patent; Kyowa Hakko Kirin Co., Ltd.; YAMAMOTO, Keisuke; ARATAKE, Seiji; HEMMI, Kazuki; EP2543670; (2013); A1;,
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Synthetic Route of 22276-97-7 ,Some common heterocyclic compound, 22276-97-7, molecular formula is C6H4BrN3O, 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.

Ste 2: (0345) (0346) Preparation of tert-butyl 5-bromo-4-oxo-3H-pyrrolo[2,3-d]pyrimidine-7(4H)-carboxylate: (0347) [00157] To a solution of 5-bromo-3H-pyrrolo[2,3-d]pyrimidin-4(7H)-one (7.1 g, 33.17 mmol) in N,N-dimethyl formamide (150 mL) were added 4-dimethylaminopyridine (DMAP) (0.406 mL, 3.31 mmol)) and di-tert-butyl dicarbonate [(Boc)2O] (6.46 mL, 28.19 mmol) at 0C. The reaction mixture was stirred at 0C for 2 h. The reaction mixture was quenched with cold water (1000 mL) and stirred for 30 minutes. The precipitated solid was filtered and dried under suction to afford the title compound tert-butyl 5-bromo-4-oxo-3H-pyrrolo[2,3-d]pyrimidine- 7(4H)-carboxylate as off white solid (8.1 g, crude). Calculated (M+H): 314.1; Found (M+H): 314.0.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,22276-97-7, its application will become more common.

Reference:
Patent; LUC THERAPEUTICS; ANDERSON, David, R.; VOLKMANN, Robert, A.; MENNITE, Frank, S.; FANGER, Christopher; (390 pag.)WO2017/100591; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 63206-77-9, Adding some certain compound to certain chemical reactions, such as: 63206-77-9, name is [1,2,4]Triazolo[4,3-a]pyrimidin-3(2H)-one,molecular formula is C5H4N4O, 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 63206-77-9.

A mixture of 2H,3H-[1,2,4]triazolo[4,3-a]pyrimidin-3-one (20 mg, 0.15 mmol) (Intermediate 22) , 2-bromo-N-[(1S)-1-(4-chloro-3- fluorophenyl)ethyl]acetamide (43 mg, 0.15 mmol) (Intermediate 3) and potassium carbonate (61 mg, 0.44 mmol) in acetonitrile (2 mL) was heated to 60 C for 3 hours. The reaction was cooled and quenched into water. The aqueous layer was extracted into ethyl acetate three times, the combined organics were washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was triturated with ethyl acetate and the solid material dried in vacuo to yield the title compound (22 mg, 43% yield).1H NMR (500 MHz, DMSO-d6) d 8.62 (d, J = 7.7 Hz, 1H), 8.55 (dd, J = 2.0, 3.8 Hz, 1H), 8.37 (dd, J = 2.0, 7.0 Hz, 1H), 7.54 (t, J = 8.1 Hz, 1H), 7.36 (dd, J = 1.9, 10.7 Hz, 1H), 7.20 (dd, J = 1.9, 8.3 Hz, 1H), 6.73 (dd, J = 3.8, 7.0 Hz, 1H), 4.94 (p, J = 7.0 Hz, 1H), 4.64 (d, J = 16.6 Hz, 1H), 4.59 (d, J = 16.6 Hz, 1H), 1.37 (d, J = 7.0 Hz, 3H). LCMS (Analytical Method A) Rt = 2.31min, MS (ESIpos): m/z= 350 [M+H]+, Purity = 98%.

According to the analysis of related databases, 63206-77-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BLACKTHORN THERAPEUTICS, INC.; JONES, Robert M.; BRANDT, Gary; (506 pag.)WO2020/97609; (2020); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 43024-61-9, 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. 43024-61-9, name is Ethyl 7-hydroxypyrazolo[1,5-a]pyrimidine-6-carboxylate. A new synthetic method of this compound is introduced below.

Stage 1.2: 7-Chloro-pyrazolo[1,5-a]pyrimidine-6-carboxylic acid ethyl ester Literature reference:. 7-Hydroxy-pyrazolo[1,5-a]pyrimidine-6-carboxylic acid ethyl ester (8.98 g; 43.3 mMol) (Example 1; stage 1.1) is suspended in POCI3 (100 mL) followed by addition of N,N-diethylaniline (11.76 mL; 73.2 mMol) at RT. The slightly yellowish suspension is slowly heated to relux (oil bath at 120C) and kept stirring for 2 h. After cooling to RT, most of the POCl3 is removed under reduced pressure. The oily residue is poured into ice water (400 mL), followed by extraction with TBME (3 x 250 mL). The combined organics are washed with NaHCO3 satd. solution (2 x 100 ML) and water, dried (Na2SO4), concentrated under reduced pressure and recrystallized from n-heptane to the title compound 1.2 as yellow crystals (3.65 g); mp. 93-95 C; HPLC: tRet = 4.73 minutes (System1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,43024-61-9, its application will become more common.

Reference:
Patent; Novartis AG; EP1918291; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 15846-19-2, 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 15846-19-2, name is 4-Chloro-6-methoxypyrimidin-5-amine. This compound has unique chemical properties. The synthetic route is as follows.

Example P1 Preparation of STR6 N-(3′-Chloro-2′,6′-dinitro-4′-trifluoromethylphenyl)-5-amino-4-chloro-6-methoxypyrimidine 2.84 g (17.8 mmoles) of 5-amino-4-chloro-6-methoxypyrimidine are dissolved in 20 ml of dimethylsulfoxide. With stirring, a solution of 6.24 g (20.5 mmoles) of 1,3-dichloro-2,6-dinitro-4-trifluoromethylbenzene in 15 ml of dimethylsulfoxide and a solution of 2.30 g (20.5 mmoles) of potassium tert-butylate in 15 ml of dimethylsulfoxide are added simultaneously dropwise at 15 C. The dark red solution so obtained is stirred for 1 hour at 15-20 C. and then poured into ice-water, neutralised with acetic acid and extracted three time with chloroform. The extracts are dried over sodium sulfate and the solvent is removed by rotary evaporation, affording 7.9 g of an oil. This crude product is purified by chromatography through a column of silica gel affording 3.19 g of a crystalline product. Recrystallisation from a mixture of 2 ml of toluene and 8 ml of cyclohexane yields 2.52 g of yellow crystals of m.p. 114-116 C.

According to the analysis of related databases, 15846-19-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Ciba-Geigy Corporation; US4840662; (1989); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 15846-19-2, 4-Chloro-6-methoxypyrimidin-5-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, HPLC of Formula: C5H6ClN3O, blongs to pyrimidines compound. HPLC of Formula: C5H6ClN3O

[Reference Example 1]; 4-Chloro-N-(4-chloro-6-methoxy-5-pyrimidinyl)-3-nitrobenzamide; 4-Chloro-3-nitrobenzoic acid (30.2 g, 150 mmol) was suspended in ethyl acetate (150 mL), and thionyl chloride (22 mL, 300 mmol) was added to the resulting suspension. The suspension was then heated under refluxing for 5 hours. The reaction mixture was concentrated under reduced pressure. The residue was concentrated utilizing two portions of dry benzene and two portions of dichloromethane. The resulting acid chloride was dissolved in dichloromethane (20 mL), and the resulting solution was added to a solution of 5-amino-4-chloro-6-methoxypyrimidine (16.0 g, 100 mmol) in dichloromethane (100 mL). The resulting mixture was heated under refluxing for 16 hours. The heated mixture was then cooled to room temperature, and the precipitated crystalline product was collected by filtration and washed with four portions of dichloromethane (20 mL), to obtain 34.3 g (yield 100%) of the titled compound as a white crystalline product. 1H-NMR (CDCl3) delta : 4.07 (3H, s), 7.35 (1H, s), 7.74 (1H, d, J=8Hz), 8.08 (1H, dd, J=2Hz, 8Hz), 8.42 (1H, d, J=2Hz), 8.55 (1H, s).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,15846-19-2, 4-Chloro-6-methoxypyrimidin-5-amine, and friends who are interested can also refer to it.

Reference:
Patent; Nippon Chemiphar Co., Ltd.; EP1757610; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia