Tag: M.W:100-200

Application of 91717-22-5, 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. 91717-22-5, name is 2-Amino-4-piperidino-6-methylpyrimidine, molecular formula is C10H16N4, 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.

General procedure: Briefly, 4-methyl-6-(piperidin-1-yl)pyrimidin-2-amine 1 (0.30 mmol), benzaldehyde 2a (0.30 mmol), 10 equiv of dimethyl malonate 3a (3 mmol), and chiral catalyst Q4(10 mol%) were added to capped vials at 60C and stirred for 36 h. After completion of the reaction, as observed by TLC, the mixture was directly purified by column chromatography on silica gel (EtOAc/hexane=8:1), affording the product (R)-4a. However, the product (S)-4a was obtained using the Q5 catalyst. Enantiomeric excess of the product was determined by HPLC analysis using a Chiralpak IA column.

According to the analysis of related databases, 91717-22-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Bai, Song; Liu, Shan; Zhu, Yunying; Zhao, Kunhong; Wu, Qin; Synlett; vol. 29; 14; (2018); p. 1921 – 1925;,
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. 3073-77-6, name is 2-Amino-5-nitropyrimidine. A new synthetic method of this compound is introduced below., HPLC of Formula: C4H4N4O2

Example 162; N-[2-(Acetylamino)pyrimidin-5-yl]-4-(4-phenyl-1,3-thiazol-2-yl)piperazine-1-carboxamide; (1) N-(5-Nitropyrimidin-2-yl)acetamide; To a solution of 2-amino-5-nitropyrimidine (3.00 g, 21.4 mmol), 4-dimethylaminopyridine (2.61 g, 21.4 mmol) and pyridine (10.4 ml, 128 mmol) in acetonitrile (100 ml) was added acetyl chloride (3.04 ml, 42.8 mmol), the mixture was stirred at 100C for 1 hour. To the mixture was added acetyl chloride (2.00 ml, 28.1 mmol) and the mixture was stirred at 100C for 12 hours. The reaction mixture was poured into ice-water and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was recrystallized from a mixed solvent of hexane and ethyl acetate to obtain the desired product (1.22 g, 31.3%) as a solid. 1H-NMR (CDCl3) delta; 2.59 (3H, s), 8.88 (1H, br s), 9.36 (2H, 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, 3073-77-6, 2-Amino-5-nitropyrimidine.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP1813606; (2007); 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. 1514-96-1, name is 4-Chloro-2-(trifluoromethyl)pyrimidine, the common compound, a new synthetic route is introduced below. category: pyrimidines

To a mixture of (S)-2-amino-4-((2-(2,2-difluoroethoxy)ethyl) (4-(5,6,7,8- tetrahydro-1,8-naphthyridin-2-yl) butyl)amino) butanoic acid hydrochloride (150 mg, 332 mumol) in THF (1.6 mL) and H2O (0.4 mL) was added NaHCO3 (140 mg, 1.66 mmol) and then 4-chloro-2-(trifluoromethyl)pyrimidine (67 mg, 366 mumol) and the resulting mixture was heated to 70 C. for 1 h, cooled to rt, adjusted to pH=6 by the addition of 1 M aq. HCl, and then concentrated in vacuo. The crude residue was purified by prep-HPLC to give the title compound. LCMS (ESI+): m/z=561.2 (M+H). H NMR (400 MHz, Methanol-d4) delta ppm 8.25 (br d, J=6.11 Hz, 1H) 7.59 (d, J=7.34 Hz, 1H) 6.88 (d, J=6.11 Hz, 1H) 6.64 (d, J=7.34 Hz, 1H) 5.82-6.17 (m, 1H) 4.83 (br s, 1H) 3.95 (br s, 2H) 3.77 (td, J=14.70, 3.61 Hz, 2H) 3.45-3.57 (m, 5H) 3.32-3.45 (m, 3H) 2.72-2.90 (m, 4H) 2.43-2.56 (m, 1H) 2.25-2.40 (m, 1H) 1.70-2.03 (m, 6H).

The synthetic route of 1514-96-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pliant Therapeutics, Inc.; CHA, Jacob; DONG, Chengguo; HOM, Timothy; JIANG, Lan; LEFTHERIS, Katerina; LI, Hui; MORGANS, JR., David J.; MUNOZ, Manuel; REILLY, Maureen; ZHENG, Yajun; (232 pag.)US2019/276449; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
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Synthetic Route of 5399-92-8, 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. 5399-92-8, name is 4-Chloro-1H-pyrazolo[3,4-d]pyrimidine. A new synthetic method of this compound is introduced below.

EXAMPLE 107; 4-(7-(benzyloxy)-lH-benzordlimidazol-2-yl)-l-(lH-pyrazolor3,4-dlpyrimidin-4- yl)piperidin-4-amine107 A. Methyl 4-(tert-butoxycarbonylamino)-l-(lH-pyrazolor3,4-dlpyrimidin-4- yl)piperidine-4-carboxylateTriethylamine (25.3 mL, 181.81 mmol) was added in one portion to a stirred suspension of methyl 4-(t°t-butoxycarbonylamino)piperidine-4-carboxylate (10.80 g, 41.82 mmol) and 4-chloro-lH-pyrazolo[3,4-d]pyrimidine (5.62 g, 36.36 mmol)** in ethanol (175 mL) at 2O0C under nitrogen. The resulting solution was stirred at 2O0C for 30 minutes and at 5O0C for 10 minutes. The solution was filtered and the filtrate was evaporated. The crude product was purified by flash silica chromatography, elution gradient 2 to 8% MeOH in DCM. Pure fractions were evaporated to dryness to afford methyl 4-(tert- butoxycarbonylamino)- 1 -( 1 H-pyrazo Io [3 ,4-d]pyrimidin-4-yl)piperidine-4-carboxylate (9.94 g, 72.6 %) as a cream dry film, m/z (ESI+) M+ = 377; HPLC tR = 1.24 min; IH NMR (399.9 MHz, DMSO-d6) delta 1.41 (9H, s), 1.92 – 1.97 (2H, m), 2.07 – 2.10 (2H, m), 3.57 (2H, m), 3.63 (3H, s), 4.34 (IH, s), 7.53 (IH, s), 8.24 (IH, s), 8.30 (IH, s), 13.52 (IH, s).H= * Commercially available from Chontech (catalogue number: 07044)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,5399-92-8, 4-Chloro-1H-pyrazolo[3,4-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; THE INSTITUTE OF CANCER RESEARCH:ROYAL CANCER HOSPITAL; CANCER RESEARCH TECHNOLOGY LIMITED; ASTRAZENECA AB; WO2008/75109; (2008); A1;,
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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. 123240-66-4, name is N-(4,6-Dichloropyrimidin-5-yl)formamide, the common compound, a new synthetic route is introduced below. Safety of N-(4,6-Dichloropyrimidin-5-yl)formamide

4,6-Dichloro-5-formamidopyrimidine 20 (0.6 g; 3.3 mmol) andDIPEA (1.8 mL; 10.4 mmol) were added to a solution of 3-amino-1-trityloxymethylphospholane 1-oxide 16 (1.0 g; 2.6 mmol) in nbutanol(25 mL). The reaction mixturewas stirred for 40 h at 130 Cand evaporated. The residue was treated 5 days at r.t. with aqueousammonia/acetonitrile 1/1 (25 mL) and evaporated. The crudeadenine derivativewas treated at 60 C for 16 h with 80% acetic acidin water (100 mL), diluted with water (100 mL) and treated withDowex 50 (H form, 5 g). The resinwas filtered off andwashed withmethanol (100 mL) and water (100 mL). The product was washedoff of the resin with 5% aqueous ammonia (100 mL), evaporated,purified by preparative HPLC (elution with gradient of 0e20%methanol in water) and freeze-dried from water to yield 0.37 g(54%) of white lyofilisate.IR nmax (KBr) 3316, 3153, 2925, 2855, 1650, 1605, 1574, 1485,1425, 1335, 1310, 1212, 1174, 1146, 1081, 796, 730, 644.HRMS (FAB) calcd for C10H15N5O2P (M H) 268.0963, found268.0962.

The synthetic route of 123240-66-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Pav, Ond?ej; Bud??insky, Milo?; Rosenberg, Ivan; Tetrahedron; vol. 73; 34; (2017); p. 5220 – 5228;,
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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 32779-36-5, name is 5-Bromo-2-chloropyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Safety of 5-Bromo-2-chloropyrimidine

The subtitle compound was prepared following a method by Takahashi et al., Chem.Pharm. Bull, 1958, 6, 334-337. To a solution of 5-bromo-2-chloropyrimidine (1.0 g, 5.2mmol) in EtOH was added sodium methanethiolate (0.36 g, 5.2 mmol) at roomtemperature and the reaction mixture was stirred overnight. The mixture was partitionedbetween EtOAc (15 mL) and water (10 mL). The aqueous layer was extracted twice withEtOAc and washed with brine. The combined organic layers were dried and concentratedto give the subtitle compound as a white solid (1.1 g).^-NMR (CD3OD): 5 8.66 (2H, s); 2.54 (3H, s).APCI-MS m/z: 204/206 1:1 [MH+].

With the rapid development of chemical substances, we look forward to future research findings about 32779-36-5.

Reference:
Patent; ASTRAZENECA AB; WO2006/4532; (2006); 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.5604-46-6, name is 2-Amino-4,6-dichloropyrimidine-5-carbaldehyde, molecular formula is C5H3Cl2N3O, molecular weight is 192.0028, as common compound, the synthetic route is as follows.Recommanded Product: 2-Amino-4,6-dichloropyrimidine-5-carbaldehyde

l-(2-hydrazinylethyl)-4-(4-(2-methoxyethoxy)phenyl)piperazine (5) (1.0 eq.) and sodium carbonate (1.1 eq.) were added to acetonitrile (40 mL) and stirred at 25-30 C. A solution of 2-amino-4,6-dichloropyrimidine-5-carboxaldehyde (4) (1 eq.) in acetonitrile (15 mL) was added. The reaction mixture was heated to 80 C and stirred with periodic TLC or HPLC monitoring. After completion of the reaction (16 h), the mixture was cooled to 20- 25 C, filtered and concentrated under reduced pressure. The crude product is pure enough for use in the next step or it can be purified by chromatography.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,5604-46-6, 2-Amino-4,6-dichloropyrimidine-5-carbaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; MAPI PHARMA LTD.; MAROM, Ehud; MIZHIRITSKII, Michael; RUBNOV, Shai; WO2012/127472; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 4316-94-3, 6-Chloro-5-nitropyrimidin-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, Product Details of 4316-94-3, blongs to pyrimidines compound. Product Details of 4316-94-3

EXAMPLE 9C1-(4-Aminophenyl)-3-(6-aminopyrimidin-4-ylamino)propan-1-one6-Chloro-5-nitro-pyrimidin-4-ylamine (379 mg, 2.1 mmol) in THF (2 mL) was added to an ice cold solution of Example 9B (510 mg, 2.1 mmol) in THF (20 mL) and ethanol (20 mL). The mixture was stirred at 0 C for 20 min, at room temperature for 1 hr and heated at 75 C for 2 h. The mixture was allowed to cool to room temperature, diluted with water (50 mL), concentrated, and filtered. The filter cake was washed with water and dried to give 0.55 g (83% yield) of the title compound. MS(ESI(+)) m/e 303.0 (M+H)+.

The synthetic route of 4316-94-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBOTT LABORATORIES; US2011/105476; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 34771-45-4, 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.34771-45-4, name is 5-Phenylpyrimidine, molecular formula is C10H8N2, molecular weight is 156.18, as common compound, the synthetic route is as follows.

A mixture of palladium complex SI (27.7 mg, 50.0 muiotaetaomicron, 5.00 mol%) and 2-chloro- phenanthroline (10.7 mg, 50.0 muiotaetaomicron, 5.00 mol%.) was dissolved in acetonitrile (5.0 mL). This mixture was added to a 20 mL vial containing a solution of Selectfluor (709 mg, 2.00 mmol, 2.00 equiv.) and 5-phenylpyrimidine (156 mg, 1.0 mmol, 1.0 equiv.) in acetonitrile (5.0 mL, final c = 0.10 M). The reaction mixture was stirred for 14 hours at 50 C and then transferred to a separately funnel. Ethyl acetate (50 mL) was added and the organic layer was washed with water (50 mL) with brine added (10 mL). The aqueous layer was extracted with dichloromethane (3 chi 50 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo at 40 C to afford a pale yellow solid. The residue was dissolved in dichloromethane (2 mL), loaded onto a short plug of silica (20 g) and eluted with ethyl acetate/dichloromethane 20:80 (v/v) and concentrated in vacuo to afford a yellow- orange solid (123 mg) containing the title compounds (111 mg, 0.580, 58% yield, 3ia: 3ib (52:48)), 5-phenylpyrimidine and minor inseparable impurities. The yield and selectivity were determined by 19F using l,4-bis(trifluoromethyl)benzene as an internal standard (standard: delta -63.4 ppm, 6 F; compared with product peaks at delta -112.4 and -117.5 ppm; first relaxation time of 10 s to ensure accurate integration). The spectra matched the reported spectra for the title compound 5ib. See Liu et al., Chem. Commun., 2009, 6267-6269. (0419) R/= 0.45 (ethyl acetate/dichloromethane 20:80 (v/v)). HRMS-FIA(m/z) calculated for CioFN2 [M+H]+, 175.0666; found, 175.0667. (0420) [00210] NMR Spectroscopy: 13C NMR (125 MHz, CDC13, 23 C, delta): 163.5 (d, J= 249.7 Hz), 159.9 (d, J = 249.7 Hz), 157.7, 157.6, 157.6, 156.4 (d, J= 4.1 Hz), 155.0, 154.8, 134.4 (d, J = 8.3 Hz), 131.1 (d, 7= 8.3 Hz), 130.2 (d, 7= 2.9 Hz), 129.8 (d, 7= 1.8 Hz), 129.5, 129.1, 128.9 (d, J= 8.4 Hz), 127.1, 125.2, 125.1, 116.7 (d, J= 21.8 Hz), 116.6 (d, J= 22.0 Hz). 5- (2-fluorophenyl)pyrimidine (3ia): 1H MR (500 MHz, CDC13, 23 C, delta): 9.15 (s, 1H), 8.91 – 8.84 (m, 3H), 7.55 – 7.33 (m, 4H), 7.27 – 7.10 (m, 3H). 19F NMR (470 MHz, CDC13, 23 C, delta): -117.5 ppm. 5-(4-fluorophenyl)pyrimidine (3ib): 1H NMR (500 MHz, CDC13, 23 C, delta): 9.21 (d, J= 1.2 Hz, 1H), 8.96 (s, 1H), 8.92 (s, 1H), 7.62 – 7.51 (m, 3H), 7.50 – 7.44 (m, 1H), 7.22 (t, J= 8.6 Hz, 1H). 19F NMR (500 MHz, CDC13, 23 C, delta): -112.4 ppm.

The chemical industry reduces the impact on the environment during synthesis 34771-45-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; PRESIDENT AND FELLOWS OF HARVARD COLLEGE; RITTER, Tobias; GARBER, Jeffrey; YAMAMOTO, Kumiko; (143 pag.)WO2017/156265; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 271-70-5, 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. 271-70-5, name is 7H-Pyrrolo[2,3-d]pyrimidine, molecular formula is C6H5N3, 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 solution of 5-bromo-1,3-dihydrobenzo[c]thiophene (1, 0.18 g, 0.81 mmol) in dimethylformamide (3.5 mL), were added 7H-pyrrolo [2,3-d]pyrimidine (2, 0.14 g, 1.22 mmol) and sodium tert-butoxide (0.12 g, 1.2 mmol). The reaction mixture was degassed with argon for 20 min. Trans-N,N?-dimethyl cyclohexane 1,2 diamine (0.064 g, 0.4 mmol) and copper(I) iodide (0.030 g, 0.16 mmol) were then added and the reaction mixture was heated at 100 C. for 16 h. After heating the reaction mixture was filtered through celite and the filtrate was concentrated under reduced pressure. The residue thus obtained was purified by silica gel column chromatography using 2% methanol in dichloromethane as eluent to afford 7-(1,3-dihydrobenzo[c]thiophen-5-yl)-7H-pyrrolo[2,3-d]pyrimidine (Cpd. No. 13). Yield: 0.029 g, 12%; MS (ESI) m/z 254[M+1]+; 1H NMR (400 MHz, DMSO-d6) delta 9.13 (s, 1H), 8.87 (s, 1H), 8.03 (d, J=3.7 Hz, 1H), 7.84 (d, J=2.0 Hz, 1H), 7.74 (dd, J=8.3, 2.1 Hz, 1H), 7.50 (d, J=8.2 Hz, 1H), 6.88 (d, J=3.7 Hz, 1H), 4.34-4.26 (m, 4H).

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 271-70-5, 7H-Pyrrolo[2,3-d]pyrimidine.

Reference:
Patent; EFFECTOR THERAPEUTICS, INC.; Sprengeler, Paul A.; Reich, Siegfried H.; Ernst, Justin T.; Webber, Stephen E.; (55 pag.)US2017/121339; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia