Category: pyrimidines

Adding a certain compound to certain chemical reactions, such as: 175277-33-5, 4-(Dimethoxymethyl)-2-methylpyrimidine, 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: C8H12N2O2, blongs to pyrimidines compound. Formula: C8H12N2O2

3N HClaq (30 mL, 90.00 mmol) was added to 4-(dimethoxymethyl)-2-methylpyrimidine (3 g, 17.84 mmol) at room teperature. The resulting solution was stirred at 50 C for 4 hours. The solvent was removed under reduced pressure to afford 2-methylpyrimidine-4- carbaldehyde (2.50 g, 88 %) as a red oil. ?H NMR (DMSO, 24 C, 400Hz) 2.81 (3H, s), 7.71(1H, d), 9.02 (1H, d), 9.93 (1H, s). mlz (ES+), [M+H]+ = 123.

The synthetic route of 175277-33-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; WARD, Richard, Andrew; GRAHAM, Mark, Andrew; SWALLOW, Steven; JONES, Clifford, David; (282 pag.)WO2016/162325; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 25746-87-6 ,Some common heterocyclic compound, 25746-87-6, molecular formula is C7H10N2O2, 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.

Pyrimidine-4-carbaldehyde (C12) A solution of 4-(dimethoxymethyl)pyrimidine (C11) (90 g, 0.58 mol) and concentrated hydrochloric acid (10 mL) in water (300 mL) was heated at 60-70 C. for 24 hours. The mixture was cooled and evaporated under reduced pressure to afford a glass-like mass, which was basified with aqueous potassium carbonate solution and extracted with ethyl acetate. The combined organic layers were concentrated in vacuo, and the residue was purified by distillation to afford the product as an oil. Yield: 16.3 g, 0.15 mol, 26%. GCMS m/z 108.0 (M+). 1H NMR (400 MHz, DMSO-d6) delta 7.90 (dd, J=5.0, 1.5 Hz, 1H), 9.14 (d, J=5.0 Hz, 1H), 9.49 (d, J=1.5 Hz, 1H), 9.96 (s, 1H).

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. 25746-87-6, 4-Dimethoxymethylpyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Pfizer Inc; US2011/98272; (2011); A1;,
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Pyrimidine – Wikipedia

Synthetic Route of 20924-05-4 ,Some common heterocyclic compound, 20924-05-4, molecular formula is C7H8N2O4, 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.

Example 20 N-[2-(Benzothiazole-2-sulfonylamino)-ethyl]-N-[(thymin-1-yl)-acetyl]-glycine ethyl ester To the mixture of N-[2-(benzothiazole-2-sulfonylamino)-ethyl]-glycine ethyl ester (1.72 g, 5 mmol), (thymin-1-yl)-acetic acid (0.92 g, 5 mmol), HOBt (0.81 g, 6 mmol), and DCC (1.24 g, 6 mmol) in DMF (15 ML) was added N,N-diisopropylethylamine (1.31 ML, 7.5 mmol) at ambient temperature.The resulting reaction mixture was stirred for 5 h at the same temperature and the solvent was removed in vacuo to 5 ML. The residue was dissolved in dichloromethane (50 ML) and the precipitate was filtered.The filtrate was washed with 1N HCl aqueous solution, saturated sodium bicarbonate solution, and brine.The organic layer was dried over magnesium sulfate and filtered.The filtrate was concentrated and the residue was triturated with ethyl alcohol.The resulting solid was filtered off and dried in vacuo to give the title compound (1.91 g, 75%) as a white solid. 1H NMR (500 MHz; DMSO-d6) delta 11.29 (s, 0.6H), 11.28(s, 0.4H), 8.99(brs, 0.6H), 8.82(brs, 0.4H), 8.28(m, 1H) 8.18(d, 1H) 7.66(m, 2H) 7.31(s, 0.6H) 7.42(s, 0.4H) 4.66(s, 1.2H) 4.47(s, 0.8H) 4.31(s, 0.8H), 4.05(s, 1.2H), 4.04(q, 1.2H), 3.55(t, 1.2H), 3.40~3.34(m, 2.8H), 3.20(t, 0.8H), 1.73(s, 3H), 1.19(t, 1.2H), 1.14(t, 1.8H).

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. 20924-05-4, 2-(5-Methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Kim, Sung Kee; Lee, Hyunil; Lim, Jong Chan; Choi, Hoon; Jeon, Jae Hoon; Ahn, Sang Youl; Lee, Sung Hee; Yoon, Won Jun; US2003/225252; (2003); A1;,
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Pyrimidine – Wikipedia

Reference of 114969-66-3, 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. 114969-66-3, name is 5-Bromo-4-cyanopyrimidine, molecular formula is C5H2BrN3, 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 41A Ethyl 3-aminothieno[3,2-d]pyrimidine-2-carboxylate 5-Bromo-4-cyanopyrimidine (2.10 g, 11.4 mmol), prepared by the method of Yamanaka, et al., Chem. Pharm. Bull., 35:3119 (1987), was treated with 1.38 g (11.5 mmol) ethyl thioglycolate and 1.21 g (11.4 g) sodium carbonate in 36 ml of refluxing ethanol. After 3 hours, the reaction mixture was cooled to room temperature, quenched with water and concentrated. The residue was purified by column chromatography on silica gel eluding first with 4:1 then 1:1 hexanes: ethyl acetate to give 1.10 g (43%) of the title compound, mp 139-141 C. 1 H NMR (300 MHz, CDCl3) delta 1.42 (t, 3H), 4.41 (q, 2H), 6.17 (br s, 2H), 9.19 (s, 1H), 9.20 (s, 1H). MS (DCI/NH3) m/e 224 (M+H)+, 241 (M+NH4)+.

According to the analysis of related databases, 114969-66-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Abbott Laboratories; US5597823; (1997); A;,
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Pyrimidine – Wikipedia

Synthetic Route of 52854-14-5, 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.52854-14-5, name is 4-Chloro-6-methoxy-5-nitropyrimidine, molecular formula is C5H4ClN3O3, molecular weight is 189.56, as common compound, the synthetic route is as follows.

General procedure: 4-chloro-6-methoxy-5-nitro-pyrimidine (Preparation R1a; 1.0 eq.), the appropriate phenol (1.2 eq.), and potassium carbonate (1.2 eq.) were dissolved in acetonitrile. It was stirred at 80 C till completion, then water was added to the reaction mixture. MeCN was evaporated. The residue extracted with DCM. The combined organic phase was dried over MgS04 and evaporated under reduced pressure to give R2a-R2ce.

Statistics shows that 52854-14-5 is playing an increasingly important role. we look forward to future research findings about 4-Chloro-6-methoxy-5-nitropyrimidine.

Reference:
Patent; LES LABORATOIRES SERVIER; VERNALIS (R&D) LIMITED; WEBER, Csaba; KOTSCHY, Andras; VASAS, Attila; KISS, Arpad; MOLNAR, Balazs; MACIAS, Alba; FIUMANA, Andrea; DAVIES, Nicholas; MURRAY, James Brooke; SELLIER, Emilie; DEMARLES, Didier; IVANSCHITZ, Lisa; GENESTE, Olivier; (233 pag.)WO2020/8013; (2020); A1;,
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Pyrimidine – Wikipedia

Reference of 29458-38-6, 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. 29458-38-6, name is 6-Methoxypyrimidine-2,4(1H,3H)-dione. A new synthetic method of this compound is introduced below.

A stirred solution of 6-methoxypyrimidine-2, 4-diol 29 (7 g, 49.30 mmol) in phosphoryl chloride (150 mL) under argon atmosphere was heated to reflux for 4 h. The reaction was monitored by TLC; after completion of the reaction, the excess phosphoryl chloride was removed in vacuo. The residue was diluted with ice-cold water (100 mL) and extracted with EtOAc (2 x 100 mL). The combined organic extracts were washed with aqueous saturated NaHC03 solution (50 mL) followed by water (50 mL), dried over sodium sulfate, filtered and concentrated in vacuo to obtain the crude compound 30 (3 g, 34%) as colorless oily liquid. TLC: 10% EtOAc/ hexanes (Rf. 0.7); 1H-NMR (CDC13, 500 MHz): delta 6.72 (s, 1H), 4.03 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,29458-38-6, 6-Methoxypyrimidine-2,4(1H,3H)-dione, and friends who are interested can also refer to it.

Reference:
Patent; INDIANA UNIVERSITY RESEARCH AND TECHNOLOGY CORPORATION; ARNOLD, Lee Daniel; MAAG, Hans; TURNER, JR., William W.; (274 pag.)WO2016/168619; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 87253-62-1 , The common heterocyclic compound, 87253-62-1, name is 5,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-carboxylic acid, molecular formula is C8H8N4O2, 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: In 25ml RB flask to a solution of Compound 9 (200 mg) in dry DMF (5ml), EDCI (250 mg, 1.25eq) and DMAP (130 mg,1eq) were added followed by addition of Sulfonamide (1eq). RM was stirred at RT for 4hrs. Solvent from the reaction mixture was evaporated. To the residue water was added and acidified with 6N HCl, solid precipitated out. Solid was filtered and dried. Crude solid was purified by flash chromatography eluating with 4-8% MeOH/DCM as solvent system to give pure product.

The synthetic route of 87253-62-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Patil, Vikas; Kale, Manoj; Raichurkar, Anandkumar; Bhaskar, Brahatheeswaran; Prahlad, Dwarakanath; Balganesh, Meenakshi; Nandan, Santosh; Shahul Hameed; Bioorganic and Medicinal Chemistry Letters; vol. 24; 9; (2014); p. 2222 – 2225;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 923282-39-7, 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.923282-39-7, name is 7-Chloro-1-methyl-1H-pyrazolo[4,3-d]pyrimidine, molecular formula is C6H5ClN4, molecular weight is 168.58, as common compound, the synthetic route is as follows.

Compound 77: 76 (0.3 g, 0.84 mmol) was added to a solution containing 9 (0.14 g, 0.84 mmol) and Hunig’s base (0.7 mL, 4.2 mmol) in DMF (5 mL). The reaction mixture was heated to 90 C. and stirred for 1 hour. The reaction mixture was cooled to room temperature. The reaction mixture was diluted with H2O and extracted the aqueous layer with EtOAc. Combined the organics, dried with MgSO4, filtered, and concentrated. The crude residue was purified by column chromatography on silica gel using 5% CH3CN in EtOAc to afford 77 (0.11 g, 31%), ES (+) MS m/e=421 (M+1).

The chemical industry reduces the impact on the environment during synthesis 923282-39-7, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Sunesis Pharmaceuticals, Inc.; US2007/27166; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 30561-07-0, Adding some certain compound to certain chemical reactions, such as: 30561-07-0, name is 2,4-Dimethoxy-5-nitropyrimidine,molecular formula is C6H7N3O4, 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 30561-07-0.

To a QianCap glass reactor (1850 mL) equipped with magnetic stirrer was added C-7A2 (100 g, 540 mmol) followed by THF (800 mL). Next, 10 % palladium on carbon (2 g) was added in one portion and the reactor was connected to the source of the hydrogen. Hydrogen pressure was set at 2 bar and reaction was well stirred for 16 h under continuous flow of hydrogen. After that time, UPLCMS analysis has shown complete conversion of starting material. The reaction mixture was filtered through the Cellite pad and the filtrate was concentrated in vacuo to around 150 – 200 mL. Then, n-hexane (500 mL) was added dropwise and the suspension was stirred for 2 h at room temperature. The precipitate was filtered, washed twice with n-hexane (2 x 50 mL) and vacuum dried. As a result, amine C-7A was obtained as a yellow/green solid (77.94 g, 93 % yeld, 99 % purity according to UPLCMS analysis).

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. 30561-07-0, 2,4-Dimethoxy-5-nitropyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Adamed sp. z o.o.; FEDER, Marcin; MAZUR, Maria; KALINOWSKA, Iwona; JASZCZEWSKA, Joanna; LEWANDOWSKI, Wojciech; WITKOWSKI, Jakub; JELEN, Sabina; WOS-LATOSI, Katarzyna; (56 pag.)EP3511334; (2019); 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. 1250967-81-7, name is 2-Chloro-4-isopropoxypyrimidine. A new synthetic method of this compound is introduced below., name: 2-Chloro-4-isopropoxypyrimidine

A mixture of (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphane) (5 mg, 8 pmol), 18F (15 mg, 0.04 mmol) ,2-chloro-4-isopropoxypyrimidine (8 mg, 0.05 mmol), BINAP (5 mg, 8 pmol), Pd2(dba)3 (2 mg, 4 pmol) and Cs2C03 (20 mg, 0.06 mmol) in toluene (1 mL) was heated in a sealed tube to 110 C overnight, then was cooled to RT and concentrated in vacuo. The residue was dissolved in THF (0.5 mL), MeOH (0.5 mL), and H20 (0.5 mL). LiOH.H20 (17 mg, 0.4 mmol) was added and the reaction was stirred at RT for 14 h, then was concentrated in vacuo. The residue was taken up in EtOAc (2 mL)/H20 (1 mL), and the solution was adjusted to pH ~ 5 with IN aq. HC1. The mixture was extracted with EtOAc (3 x 2 mL); the combined organic extracts were dried (MgS04) and concentrated in vacuo. The residue was dissolved in DMF and purified via preparative LC/MS: Column: XBridge Cl 8, 200 mm x 19 mm, 5-pm particles; Mobile Phase A: 5:95 MeCN:H20 with 0.1% TFA; Mobile Phase B: 95:5 MeCN:H20 with 0.1% TFA; Gradient: a 0-min hold at 18% B, 18-58% B over 20 min, then a 4-min hold at 100% B; Flow Rate: 20 mL/min; Column Temperature: 25 C. Fractions containing the desired product were combined and dried via centrifugal evaporation to afford the title compound (bis-TFA salt, 1 mg, 3% yield; 84% purity by LC-MS). LCMS, [M + H]+ = 468.4. NMR (500 MHz, DMSO-de) d 8.31 (s, 1H), 8.08 (d, J= 5.7 Hz, 1H), 7.92 (s, 1H), 6.18 (d, J= 5.7 Hz, 1H), 5.10 – 4.98 (m, 1H), 4.75 (s, 1H), 3.72 (s, 3H), 2.68 – 2.59 (m, 1H), 2.27 (s, 3H), 2.01 – 1.47 (m, 8H), 1.21 – 1.15 (m, 6H). hLPAi IC50 = 1014 nM.

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, 1250967-81-7, 2-Chloro-4-isopropoxypyrimidine.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; SHI, Yan; WANG, Ying; CHENG, Peter Tai Wah; LI, Jun; WALKER, Steven J.; (147 pag.)WO2019/126089; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia