Category: pyrimidines

Electric Literature of 1004-38-2 , The common heterocyclic compound, 1004-38-2, name is 2,4,6-Triaminopyrimidine, molecular formula is C4H7N5, 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: A mixture of 2,4,6-triaminopyrimidine 1 (1.0 mmol), 3-(2-cyanoacetyl)indole 2 (1.0 mmol), appropriate aromatic aldehyde (1.0 mmol) and indium chloride (0.05 mmol) in ethanol (5.0 mL) were subjected to microwave irradiation for 10 min at 120 C. After completion of the reaction (monitored by TLC using a dichloromethane-ethanol (9:1) mixture as the mobile phase), the reaction mixture was cooled and filtered. The solid product obtained was initially washed with ethanol, and finally recrystallized from ethanol.

The synthetic route of 1004-38-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Enriz, Ricardo D.; Tosso, Rodrigo D.; Andujar, Sebastian A.; Cabedo, Nuria; Cortes, Diego; Nogueras, Manuel; Cobo, Justo; Vargas, Didier F.; Trilleras, Jorge; Tetrahedron; vol. 74; 49; (2018); p. 7047 – 7057;,
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Adding a certain compound to certain chemical reactions, such as: 84905-80-6, 4-Chloro-5H-pyrrolo[3,2-d]pyrimidine, 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, 84905-80-6, blongs to pyrimidines compound. category: pyrimidines

Example 60 Production of ethyl 3-(5H-pyrrolo[3,2-d]pyrimidin-4-ylamino)benzoate A mixture of 4-chloro-5H-pyrrolo[3,2-d]pyrimidine (2.78 g), ethyl 3-aminobenzoate (4.49 g) and 1-methyl-2-pyrrolidone (20 mL) was stirred at 120C for 1.5 hrs. To the reaction mixture were added ethyl acetate, water and saturated aqueous sodium hydrogen carbonate solution. The insoluble material was filtered off, and the ethyl acetate layer was separated. The aqueous layer was extracted with ethyl acetate, and the mixed ethyl acetate layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The filtered insoluble material was suspended in methanol and ethyl acetate and saturated brine were added. The ethyl acetate layer was separated. The ethyl acetate layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The mixed ethyl acetate layer was concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography (eluent, ethyl acetate) and crystallized from methanol-acetone-diisopropyl ether to give the title compound (2.85 g) as a pale-brown powder. 1H-NMR (CDCl3) delta: 1.39 (3H, t, J= 7.2 Hz), 4.37 (2H, q, J= 7.2 Hz), 6.51 (1H, d, J= 3.3 Hz), 7.28-7.32 (1H, m), 7.42 (1H, t, J= 8.0 Hz), 7.70 (1H, d, J= 7.8 Hz), 8.09 (1H, s), 8.29 (1H, d, J= 8.1 Hz), 8.49 (1H, m).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,84905-80-6, its application will become more common.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP1752457; (2007); A1;,
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Electric Literature of 216959-91-0, 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 216959-91-0, name is 4-(Pyrimidin-5-yl)benzoic acid. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of Co(NO3)2·6H2O (0.2 mmol, 0.058 g), HL(0.020 g, 0.1 mmol), and H2O 10 mL was placed in a ParrTeflon-lined stainless steel vessel (23 mL). Then the pH valuewas tuned into 8 using NaOH solution (0.5 M). After that themixturewas heated to 160C and held for 60 h. Then the reactantmixture was cooled at a rate of 0.5C/min to lead to the formationof red block crystal 1. Yield: 37% based on HL.

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 216959-91-0, 4-(Pyrimidin-5-yl)benzoic acid.

Reference:
Article; An, Zhe; Hu, Ying-Shuang; Zhu, Li-Hua; Zhu, Ling; Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry; vol. 44; 10; (2014); p. 1435 – 1438;,
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Electric Literature of 6153-44-2, Adding some certain compound to certain chemical reactions, such as: 6153-44-2, name is Methyl 2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylate,molecular formula is C6H6N2O4, 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 6153-44-2.

To a 25 mL reaction tube, Cs2CO3 (0.8 mmol) was added.Compound A-8 (0.4 mmol, 1 equivalent),After replacing argon three times, add 3 mL of dimethyl sulfoxide (DMSO).100 muL (1.20 mmol) of Compound B in DMSO was injected.After stirring for 24 hours under blue light irradiation, Compound C-8 was obtained in a yield of 75percent.

According to the analysis of related databases, 6153-44-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Zunyi Medical College; He Chunyang; Lei Yunyun; Huang Yang; Zhao Liang; Jia Jia; Li Xiaofei; (10 pag.)CN108484508; (2018); A;,
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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. 926663-00-5, name is Ethyl 5-oxo-4,5-dihydropyrazolo[1,5-a]pyrimidine-3-carboxylate, molecular formula is C9H9N3O3, 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. Safety of Ethyl 5-oxo-4,5-dihydropyrazolo[1,5-a]pyrimidine-3-carboxylate

The 5-hydroxy pyrazole [1,5-a] pyrimidine-3-carboxylic acid ethyl ester (18.0g) suspended in acetonitrile (40 ml), at room temperature add oxygen phosphorus chloride (40 ml), and to the mixture under nitrogen atmosphere to 110 C stirring 4 hours. Cooling the reaction mixture, and the concentrated under reduced pressure. Aid hemostasis diluted with ethyl acetate and to neutralize the sodium bicarbonate aqueous solution, but insoluble material to celite filtration. The organic filtrate is purified by silicon rubber, and the evaporation of the solvent under reduced pressure. Precipitation of the solid in ethyl acetate/b isopropyl group ether cleaning in order to produce the title compound (14.1g). Mother liquor further for concentrated under reduced pressure, and the generated solid of using ethyl acetate/b isopropyl group ether cleaning in order to produce the title compound (2.40g).

With the rapid development of chemical substances, we look forward to future research findings about 926663-00-5.

Reference:
Patent; TAKED A PHARMACEUTICAL COMPANY LIMITED; KAWASAKI, MASANORI; MIKAMI, SATOSHI; NAKAMURA, SHINJI; NEGORO, NOBUYUKI; IKEDA, SHUHEI; ASHIZAWA, TOMOKO; MARUI, SHOGO; TANIGUCHI, TAKAHIKO; (135 pag.)TW2016/520; (2016); A;,
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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.21236-97-5, name is 6-Amino-3-methylpyrimidine-2,4(1H,3H)-dione, molecular formula is C5H7N3O2, molecular weight is 141.128, as common compound, the synthetic route is as follows.Computed Properties of C5H7N3O2

General procedure: A mixture of phenylisothio-cyanate 1a (1 mmol, 0.135 g), benzaldehyde 2a (1 mmol, 0.106 g) and N,N-dimethyl-6-amino uracil 3a (1 mmol, 0.155 g) in water (5 mL) was refluxed for 1 h in the presence of catalytic amount of p-TSA (20 mol %). After completion of the reaction (monitored by TLC), the mixture was cooled to room temperature, filtered and washed with water (25 mL). The crude product was purified by recrystallization from EtOH to give 4a.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,21236-97-5, 6-Amino-3-methylpyrimidine-2,4(1H,3H)-dione, and friends who are interested can also refer to it.

Reference:
Article; Majumder, Swarup; Borah, Pallabi; Bhuyan, Pulak J.; Tetrahedron Letters; vol. 55; 6; (2014); p. 1168 – 1170;,
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Related Products of 955368-90-8, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 955368-90-8 as follows.

General method for the preparation of pyridyl pyrazolopyrimidinones (9a-c). Nu,Nu’- Dimethylethylenediamine (4.47 mmol) was added to a solution of pyrazolopyrimidine 7 (2.25 mmol), bromopyridine (8a-c; 2.93 mmol), copper iodide (2.25 mmol) and K2C03 (3.1 5 mmol) in 1 ,4-dioxane (5 ml) at 80 C. The resultant suspension was heated at 95 C for 18 h, over which time a colour change of orange to dark green occurred. The reaction mixture was cooled to RT and diluted with NH40H (10 ml) before being extracted with EtOAc (2 x 20 ml). The combined organic extracts were washed with brine (20 ml), dried 33 (MgS04) and evaporated to dryness. The crude material was purified via silica gel chromatography (19:1 DCM:MeOH) to afford the target pyridyl pyrazolopyrimidinones (69-84%). 2-Allyl-1-(6-(2-hydroxypropan-2-yl)pyridin-2-yl)-6-(methylthio)-1,2-dihydro-3H- pyrazolo[3,4- d]pyrimidin-3-one (9a). Rf 0.63 (9:1 DCM:MeOH); M.p.108-111 C; IR (cm-1) 3337, 3081, 2966, 2924, 1663, 1601, 1559; 1H NMR(400 MHz, CDCI3) 1.61 (6H, s, C(CH3)2), 2.61 (3H, s, S-CH3), 3.77 (1H, s, -OH), 4.82 (2H, dapp, J = 5.9 Hz, N2-CH2), 4.95 (1H, dapp, J = 16.9 Hz, allyl C-Htrans), 5.08 (1H, dapp, J = 10.3 Hz, allyl C-Hcis), 5.72 (1H, dd = 16.9, 10.3, 5.9 Hz, allyl C-H), 7.42 (1H, d, J = 7.7 Hz, H-5′), 7.78 (1H, d,J = 8.0 Hz, H-3′), 7.93 (1H, dd,J = 8.0, 7.7 Hz, H-4′), 8.96 (1H, s, H-4); 13C NMR(125 MHz, CDCI3) 14.5 (SCH3), 30.5 (C(CH3)2), 47.5 (N2-CH2), 72.5 (C(CH3)2), 116.4 (Ar-C), 116.6 (Ar-C), 119.3 (allyl-CH2), 131.2, 139.2, 147.0 (Ar-C), 154.3 (Ar-C), 159.2 (C=0), 161.0 (Ar-C), 166.1 (Ar-C), 177.0 (Ar-C); MS [M + H]+ m/z 359.3.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,955368-90-8, its application will become more common.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF COLORADO, A BODY CORPORATE; REIGAN, Philip; MATHESON, Christopher; (71 pag.)WO2017/75629; (2017); A2;,
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Reference of 16019-31-1, 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. 16019-31-1, name is 5-Allyl-4,6-dichloropyrimidine, molecular formula is C7H6Cl2N2, 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.

Compound 1B (9.73 g, 51.47 mmol) was dissolved in an acetone: water (1 :1 , 290 mL) mixture and to the resulting solution was added potassium osmate dihydrate (0.64 g, 1.75 mmol). The reaction was allowed to stir for 5 minutes, then solid sodium periodate (4 4g, 205.37 mmol) was added in 4 portions over a 1 hour period, during which time, th reaction temperature did not exceed 40 C. The resulting suspension was was allowed to stir at room temperature for x hours for 1 hour, during which time the reaction mixture was permitted to cool to room temperature on its own. The reaction mixture was then filtered and the filtrate was concentrated in vacuo to remove acetone. The remaining aqueous layer was extracted with dichloromethane (2 x 200 mL) and the combined organic layers were washed with 10% sodium thiosulfate solution, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to provide Compound 1C (8.16 g, 83.01%), which was used without further purification.

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 16019-31-1, 5-Allyl-4,6-dichloropyrimidine.

Reference:
Patent; SCHERING CORPORATION; NEELAMKAVIL, Santhosh, Francis; BISWAS, Dipshikha; CHACKALAMANNIL, Samuel; NEUSTADT, Bernard, R.; STAMFORD, Andrew; LIU, Hong; WO2011/62885; (2011); A1;,
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Related Products 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.

In a 100 mL jar, 2-amino-4-piperidinyl-6-methylpyrimidine (0.001 mol) was added,Benzaldehyde (0.001 mol) and diethyl malonate (0.0015 mol) were added with paraxylene (30 mL) as solvent.The reaction was terminated after 50 minutes in a microwave at 100C, and paraxylene was recovered under reduced pressure.Column chromatography (petroleum ether:ethyl acetate=4:1 V/V) gave the desired product.

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 91717-22-5, 2-Amino-4-piperidino-6-methylpyrimidine.

Reference:
Patent; Guizhou Institute Of Technology; Bai Song; Zhu Yunying; Wei Xian; Wu Qin; Zou Shuliang; Tang Qin; Gong Zhihai; Zhou Han; Zhou Hang; (14 pag.)CN108101855; (2018); A;,
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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. 3177-24-0, name is 2,4-Dichloropyrimidine-5-carbonitrile, the common compound, a new synthetic route is introduced below. Safety of 2,4-Dichloropyrimidine-5-carbonitrile

Example 20. Synthesis of 2-({[3′-(aminomethyl)-2-methyIbiphenyl-3- yIJmethyl}amino)-4-(4,5,7,8-tetrahydroimidazol4,5-dlazepn-6(lH)-yl)pyrmicline-5- carbonitrile; To a solution of (3′-aminomethyl-2′-methyl-biphenyl-3-ylmethyl)-carbamic acid tert-butyl ester (281 mg, 0.86 mmol) and diisopropylethylamine (0.165 mL, 0.95 mmol) in dichloromethane (5.0 mL) was added 2,4-dichloro-pyritnidine-5-carbonitrile (150 mg, 0.86 mmol). The ixn mixture was stirred at room temperature for 70 h, then adsorbed directly onto silica gel and purified by silica gel chromatography eluting with 20-45percent ethyl acetate in hcxancs to afford 254 mg of a colorless oil, identified as a 1:1 mixture of the desired product and the regioisomeric 4-addition product. This mixture was further purified by reverse phase semi-prep HPLC using 60percent acetonitrile/water (0.1percent TFA) as eluent to give 149 mg of {3′-[(4-chloro-5-cyano-pyrimidin-2-ylamino)-methyl]-2′-methyl-biphenyl-3- yhnethyl}-carbamic acid tert-butyl ester as an off-white solid, m/z 486.0 (M + Na)+.To a solution of l,4,5,6,7,8-hexahydro-imidazo[4,5-cyano-4-(4,5,7,8-tetrahydro-lH-imidazo[4,5-c?]azepin-6-yl)-pyrimidin-2-ylamino]- methyl}-2′-methyl-biphenyl-3-ylmethyl)-carbamic acid tert-butyl ester, m/z 565.1 (M + H)+.A solution of (3′-{[5-cyano-4-(4,5,7,8-tetrahydro-lH-imidazo[4,5-Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG; WO2007/76247; (2007); A1;,
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