Pyrimidines

Electric Literature of 157335-93-8, 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. 157335-93-8, name is 4,6-Dimethylpyrimidine-5-carboxylic acid. A new synthetic method of this compound is introduced below.

Preparation of (4,6-Dimethyl-pyrimidin-5-yl)-(hexahydro-pyrrolo[3,4-clpyrrol-2- yl)-methanone (38, Ar2 = 4,6-dimethyl-pyrimidin-5-yl)To a mixture of 4,6-dimethyl-pyrimidine-5-carboxylic acid (0.85 g, 5.58 mmol, T. J. Kress et. al. Heterocydes 1994 38:1375) and 16a ( 1.13 g, 5.58 mmol, C. J. Ohnmacht et al. /. Heterocyd. Chem. 1983 20:321) in DCM (25 mL) at RT was added sequentially EDCI ( 1.43 g, 6.7 mmol), HOBt (0.9 g, 6.7 mmol) and DIPEA (3.9 mL, 22.34 mmol) and the mixture was stirred overnight at RT. The reaction mixture was washed with 5% NaHC?3 solution, dried (MgSO4) and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel eluting with MeOH (containing 10% NH4OH) /DCM (0 to 4%) to afford 1.5 g of (5-benzyl-hexahydro-pyrrolo[3,4-c]pyrrol-2-yl)-(4,6- dimethyl-pyrimidin-5-yl)-methanone: ms (ES+) m/z 337 (M + H) +.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,157335-93-8, 4,6-Dimethylpyrimidine-5-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; LEMOINE, Remy; MELVILLE, Chris Richard; ROTSTEIN, David Mark; WANNER, Jutta; WO2008/34731; (2008); A1;,
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Related Products of 74901-69-2, 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. 74901-69-2, name is 2,4-Dichloro-6,7-dihydrothieno[3,2-d]pyrimidine. A new synthetic method of this compound is introduced below.

Synthesis of Isoxazole-5-carboxylic acid-{(1S,2S)-2-[2-(4-phenylpiperazin-1-yl)-6,7-dihydrothieno[3,2-d]pyrimidin-4-ylamino]cyclopentyl}amide triflate (XI) (chiral) (According to Scheme 7) tert-butyl [(1S,2S)-2-(2-chloro-6,7-dihydrothieno[3,2-d]pyrimidin-4-ylamino)cyclopentyl]carbamate (V) (chiral): 0.600 g (2.9 mmol) of 2,4-dichloro-6,7-dihydrothieno[3,2-d]pyrimidine (III), 0.580 g (2.9 mmol) of tert-butyl (2-aminocyclopentyl)carbamate (IV), and 2.5 mL (14.5 mmol) of diisopropylethylamine are placed in 30 mL of tetrahydrofuran, the mixture is stirred for 2 hours at ambient temperature and 72 hours at 80 C. The reaction mixture is concentrated by evaporation and further reacted in the crude state.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,74901-69-2, its application will become more common.

Reference:
Patent; Boehringer Ingelheim International GmbH; US2007/259846; (2007); A1;,
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Pyrimidine – Wikipedia

Synthetic Route of 120747-84-4, 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. 120747-84-4, name is 2-Aminopyrimidine-5-carbaldehyde. A new synthetic method of this compound is introduced below.

(0209) To a solution of the compound of Reference Example 1 (30 mg, 0.129 mmol) in dichloromethane (1.5 mL) was added triethylamine (0.036 mL, 0.258 mmol), the mixture was stirred at room temperature for 10 minutes, and then 2-aminopyrimidine-5-carboxyaldehyde (15.9 mg, 0.129 mmol) and sodium triacetoxyborohydride (41.0 mg, 0.194 mmol) were added thereto. The mixture was stirred at room temperature for 1.5 hours, then sodium triacetoxyborohydride (41.0 mg, 0.194 mmol) was added thereto, and the mixture was stirred at room temperature for additional 24 hours. To the reaction mixture was then added saturated aqueous sodium hydrogen carbonate solution (20 mL), and the mixture was extracted with chloroform (20 mL) twice. The combined organic layer was dried over anhydrous sodium sulfate, filtrated, and concentrated. The resulting residue was purified by silica gel column chromatography (chloroform:methanol=100:0 to 90:10) to give the title compound (20.1 mg, 58%). (0210) 1H-NMR (400 MHz, CDCl3) delta: 2.65-2.70 (2H, m), 2.71-2.75 (2H, m), 3.20-3.24 (2H, m), 3.50 (2H, s), 4.99 (2H, brs), 6.60-6.64 (1H, m), 7.13 (1H, ddd, J=7.4, 4.8, 1.0 Hz), 7.37 (1H, d, J=8.0 Hz), 7.63 (1H, ddd, J=7.7, 7.7, 1.8 Hz), 8.30 (2H, s), 8.54-8.57 (1H, m).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,120747-84-4, 2-Aminopyrimidine-5-carbaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; Sumitomo Dainippon Pharma Co., Ltd.; YOSHINAGA, Hidefumi; URUNO, Yoshiharu; NAGATA, Hidetaka; HASHIMOTO, Masakazu; KATO, Taro; (43 pag.)US2016/122319; (2016); 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. 4349-07-9, name is 5-Iodopyrimidin-4-ol, the common compound, a new synthetic route is introduced below. category: pyrimidines

Method 0 Preparation of 4-Chloro-5-iodopyrimidine 5-Iodo-4(3H)-pyrimidinone (1 eq. ) was suspended in toluene to which was added POC13 (2.0 eq. ). The reaction mixture was heated to reflux for 3 hours, and then cooled and concentrated. The residue was suspended in water, adjusted to pH=7 by addition of 4N sodium hydroxide, and extracted with ethyl acetate. The organic extracts were washed with brine, dried (MgS04), filtered and stripped to give a red oil. The crude product was dissolved in methanol and silica gel was added. Following concentration, the coated silica gel was loaded onto a plug of silica gel and elution with ethyl acetate/hexanes yielded the title compound.

The synthetic route of 4349-07-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELAN PHARMACEUTICALS, INC.; WO2005/97162; (2005); A2;,
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Pyrimidine – Wikipedia

Related Products of 330786-24-8, 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 330786-24-8, name is 3-(4-Phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine. This compound has unique chemical properties. The synthetic route is as follows.

Under nitrogen protection, 20 g of triphenylphosphine supported by nano-Fe3O4 was added to the three-necked flask (particle diameter 100 nm,PPh3 loading 1 mmol/g), adding intermediate (II) (3.04 g, 10 mmol),N-Boc-3S-hydroxypiperidine (III) (2.02 g, 10 mmol), diethyl azodicarboxylate (3.67 g, 21.1 mol)And 1,4-dioxane (100 mL), the reaction was stirred at 20 C until the intermediate (II) was consumed completely, and the reaction was stopped.The external magnet adsorbs the magnetic nano-load, and the reaction solution is decanted, and the nanoparticles are washed with 1,4-dioxane (50 mL¡Á2).The washing liquid and the reaction liquid were combined, concentrated under reduced pressure to (20 mL), and then added to 10 mol/L hydrochloric acid (40 mL), and the mixture was completely removed.Dichloromethane (50 mL x 3) was extracted and the aqueous phase was neutralized with saturated sodium carbonate to pH >Filtration and vacuum drying to obtain a solid intermediate (IV) (3.30 g, yield: 85.3%).No residual phenoxide was detected.

According to the analysis of related databases, 330786-24-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hangzhou China-USA East China Pharmaceutical Co., Ltd.; Hangzhou East China Pharmaceutical Group New Drug Institute Co., Ltd.; Zhou Yubao; Yu Rui; Chen Yu; Hu Haiwen; (7 pag.)CN108623606; (2018); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 39268-74-1, Adding some certain compound to certain chemical reactions, such as: 39268-74-1, name is 5-Ethoxypyrimidin-2-amine,molecular formula is C6H9N3O, 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 39268-74-1.

To a 10 ml glass vial was added (RS)-2-(4-bromo-3-fluoro-phenyl)-morpholine-4-carboxylic acid tert-butyl ester (70 mg, Example 96(e)) and 5-ethoxy-2-pyrimidinamine (40.6 mg, CAS 39268-74-1) in dioxane (2 ml). The reaction mixture was purged with argon for 5 min. 2-Di-tert- butylphosphino-2′,4′,6′-triisopropylbiphenyl (13.6 mg), tris(dibenzylideneacetone)dipalladium(0) (7.12 mg) and sodium tert-butoxide (21.0 mg) were then added. The vial was capped and heated at 120 C for 16 h. The reaction mixture was then filtered through sintered glass and the filtrate was concentrated in vacuo. The residue was purified by flash column chromatography (silica gel; gradient: 0% to 50% EtOAc in hexanes) to afford (RS)-2-[4-(5-ethoxy-pyrimidin-2-ylamino)-3- fluoro-phenyl]-morpholine-4-carboxylic acid tert-butyl ester (15 mg, 18%) as a yellow gum. MS (ISP): 441.4 ([M+Na]+), 419.3 ([M+H]+).

According to the analysis of related databases, 39268-74-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GALLEY, Guido; NORCROSS, Roger; PFLIEGER, Philippe; WO2012/126922; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 1753-50-0, 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. 1753-50-0, name is 2-Chloropyrimidine-5-carbonitrile, molecular formula is C5H2ClN3, 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 stirred solution of compound JG (0.8 g, 3.07 mmol) in EtOH (15 mL) was added DIPEA (1.6 mL, 9.23 mmol) followed by 2-chloropyrimidine-5-carbonitrile (5, 0.51 g, 3.69 mmol) and the reaction mixture was stirred at 90C for 8 h. The progress of reaction was monitored by TLC. After completion of the reaction, the reaction mixture was concentrated under reduced pressure. The crude product was purified by silica gel column chromatography using 30% EtOAc/hexane to afford compound JH (0.7 g, 63.0%) as an off white solid. 1H NMR (400 MHz, DMSO-d6): _ 8.53 (brs, 1H), 8.47 (brs, 1H), 7.90 (d, / = 8.0 Hz, 1H), 7.55 (t, J = 7.4 Hz, 1H), 7.48-7.37 (m, 4H), 7.12 (t, 7 = 8.8 Hz, 2H), 5.44-5.40 (m, 1H), 3.41-3.35 (m, 1H), 3.28-3.22 (m, 1H); LC-MS: mJz 364.10 [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 1753-50-0, 2-Chloropyrimidine-5-carbonitrile.

Reference:
Patent; VPS-3, INC.; YATES, Christopher, M.; (397 pag.)WO2018/165520; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 18592-13-7, 6-(Chloromethyl)pyrimidine-2,4(1H,3H)-dione, 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, Quality Control of 6-(Chloromethyl)pyrimidine-2,4(1H,3H)-dione, blongs to pyrimidines compound. Quality Control of 6-(Chloromethyl)pyrimidine-2,4(1H,3H)-dione

Synthesis of 5-chloro-6-(chloromethyl)- l,2,3,4-tetrahydropyrimidine-2,4-dione: Into a 1- L round-bottom flask, was placed 6-(chloromethyl)- l,2,3,4-tetrahydropyrimidine-2,4-dione (15 g, 93.42 mmol, 1 equiv), acetic acid (225 mL), acetyl acetate (15 mL). The resulting solution was stirred for 30 min at 80 C in an oil bath. Then NCS (16.2 g, 121.32 mmol, 1.30 equiv) was added at 60 C. The resulting solution was stirred for 3h at 60 C in an oil bath. The reaction was then quenched by the addition of 500 mL of water/ice. The solids were collected by filtration. The solid was dried in an oven under reduced pressure. This resulted in 10.1 g of 5- chloro-6-(chloromethyl)- l,2,3,4-tetrahydropyrimidine-2,4-dione as an off-white solid. LC-MS- BLV-CY-202- 1 : (ES, m/z): 195[M+H]+. H-NMR- BLV-CY-202- 1 : (300 MHz, OMSO, ppm): delta 11.71 (s, 1H), 11.56 (s, 1H), 4.47 (s, 2H).

The synthetic route of 18592-13-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BLUEVALLEY PHARMACEUTICAL LLC; LI, Xiang; (99 pag.)WO2019/50889; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 165807-05-6, name is 4-Dimethoxymethylpyrimidin-2-ylamine, molecular formula is C7H11N3O2, 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. HPLC of Formula: C7H11N3O2

Procedure I: Intermediate 9 (1-9) – 2-Aminopyrimidine-4-carboxaldehyde.; [0095] A solution of 2.5 g (15 mmol, 1.0 eq.) of 2-aminopyrimidine-4- carboxaldehyde dimethylacetal (1-8) in 16 mL (48 mmol, 3.2 eq.) of 3M HCl was heated at 48 0C for 14 h. The mixture was allowed to cool to room temperature and diluted with 50 mL of EtOAc. The aqueous layer was neutralized with NaHCCb and then extracted with EtOAc (5 x 50 mL). The combined organic extracts were dried (Na2SO^ and the solvent removed in vacuo to provide 0.69 g (5.6 mmol, 37percent) of 2- aminopyrimidine-4-carboxaldehyde (1-9) as a yellow solid.

With the rapid development of chemical substances, we look forward to future research findings about 165807-05-6.

Reference:
Patent; PHARMACOPEIA, INC.; WO2007/104053; (2007); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 823-89-2, 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.823-89-2, name is 5-Bromo-2-hydrazinopyrimidine, molecular formula is C4H5BrN4, molecular weight is 189.01, as common compound, the synthetic route is as follows.

A mixture of A-68 (500.00 mg, 2.65 mmol) in CH(OEt)3 (882.54 _1_, 5.30 mmol) was stirred at 120 C for 16 hours The mixture was diluted with EtOH (5 mL) and the solid formed was collected by filtration, washed with EtOH (5 mL x 3) and dried in oven to afford A-71 (400.00 mg, 1.99 mmol) as a solid. H NMR (400MHz, CDC13) _ = 8.81 (s, 1H), 8.68 (d, 1H), 8.62 (d, 1H). LCMS R, = 0.15 min using Method B, MS ESI calcd. for C5H4BrN4 [M+H+2]+ 201.0, found 200.9

Statistics shows that 823-89-2 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-2-hydrazinopyrimidine.

Reference:
Patent; PRAXIS PRECISION MEDICINES, INC.; REDDY, Kiran; MARTINEZ BOTELLA, Gabriel; GRIFFIN, Andrew, Mark; MARRON, Brian, Edward; (364 pag.)WO2018/98499; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia