Category: pyrimidines

Reference of 304646-29-5 , The common heterocyclic compound, 304646-29-5, name is 2-Methoxy-5-nitropyrimidin-4-amine, molecular formula is C5H6N4O3, 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.

A mixture of compound 6 (560 mg, 3.29 mmol) in MeOH (30 mL) was added 10% Pd on carbon (56.4 mg). After the mixture was stirred at 20 C under H2 (15 psi) for 1 h, it wasfiltered and the filtrate was concentrated to give compound 7 (310 mg, 2.21 mmol, 67.2% yield) as a brown solid.

The synthetic route of 304646-29-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GENENTECH, INC.; DRAGOVICH, Peter; PEI, Zhonghua; PILLOW, Thomas; SADOWSKY, Jack; CHEN, Jinhua; WAI, John; (237 pag.)WO2017/64675; (2017); A1;,
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Adding a certain compound to certain chemical reactions, such as: 25902-86-7, 2-Methoxypyrimidin-4(1H)-one, 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, 25902-86-7, blongs to pyrimidines compound. Safety of 2-Methoxypyrimidin-4(1H)-one

A mixture of 18 g (0.0779 m) of the 2-methoxypyrimidinone, 12.23 g (0.0779 m) of alpha-furylmethylthioethylamine and 50 ml of toluene was heated at reflux for 12 hours. Toluene (100 ml) was added to the cooled reaction mixture. The separated solid was washed with ethyl acetate and dried to give 20.69 g (74%) of 2-[[2-[(2-furylmethyl)thio]ethyl]amino]-5-[(6-methyl-3-pyridinyl)methyl]-4-(1H)-pyrimidinone. Recrystallization from isopropanol-water gave 14.51 g (52%), m.p. 147-152, of purified compound. Anal. Calcd. for C18 H20 N4 O2 S: C, 60.25; H, 5.65; N, 15.71; S, 8.99. Found: C, 60.29; H, 5.33; N, 15.43; S, 8.50.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,25902-86-7, its application will become more common.

Reference:
Patent; Smithkline Beckman Corporation; US4352933; (1982); A;,
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Reference of 38275-42-2, 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 38275-42-2, name is 5-Chloro-2-(methylthio)pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 39 2-Methylsulfinyl-5-chloropyrimidine A solution of 2-methylthio-5-chloropyrimidine (13 mmol) in chloroform (85 ml) was cooled to -20 C. and m-chloroperbenzoic acid (17 mmol) added with stirring. The mixture was stirred for 40 min at -20 C. and for 4 h at 0 C. and left at this temperature overnight. The chloroform solution was then washed with 1 M potassium carbonate (3*10 ml) and the dried (MgSO4) solution evaporated. The residual oily material crystallized on standing; yield 80% m.p. 48 C. (n-heptane). 1 H NMR (CDCl3): delta2.93 (Me), 8.83 (2H-4,6).

According to the analysis of related databases, 38275-42-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Nyegaard & Co. A/S; US4423047; (1983); A;,
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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. 32998-03-1, name is 2,6-Dichloro-N-methylpyrimidin-4-amine. A new synthetic method of this compound is introduced below., COA of Formula: C5H5Cl2N3

EXAMPLE 3 4-Methylamino-2,6-di-1-pyrrolidinopyrimidine (V) Pyrrolidine (IV, 25 ml) is added (exothermic) to 2,6-dichloro-4-methylaminopyrimidine (III, EXAMPLE 1, 1.81 g). The mixture is stirred and heated under reflux for 23 hours, then is allowed to cool and concentrated under reduced pressure. The residue is partitioned between ethyl acetate and aqueous potassium bicarbonate, the phases separated and organic phase is concentrated to give a solid. The solid is crystallized from hexane to give the title compound, mp 100.5-103; NMR (CDCl3) 4.74, 3.51, 3.43, 2.81 and 1.9delta; CMR (CDCl3) 164.50, 161.92, 160.18, 70.78, 46.06, 45.85, 28.47, 25.44, 25.19delta. Alternatively, the title compound can be obtained by the reaction of 4-chloro-2,6-di-1-pyrrolidinylpyrimidine and methylamine (II) in pyridine in a pressure tube at 100, MS (M+) 247.

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, 32998-03-1, 2,6-Dichloro-N-methylpyrimidin-4-amine.

Reference:
Patent; The Upjohn Company; US5502187; (1996); A;,
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Electric Literature of 199678-12-1, Adding some certain compound to certain chemical reactions, such as: 199678-12-1, name is 4-Pyrimidin-2-yl-benzoic acid,molecular formula is C11H8N2O2, 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 199678-12-1.

Example 138 N-(4-{trans-2-[(cyclopropylmethyl)amino]cyclopropyl}phenyl)-4-(pyrimidin-2-yl)benzamide hydrochloride By a method similar to Example 80, the title compound (34.3 mg) was obtained from tert-butyl [trans-2-(4-aminophenyl)cyclopropyl](cyclopropylmethyl)carbamate (87.7 mg) and 4-(pyrimidin-2-yl)benzoic acid (69.7 mg). MS (API+): [M+H]+ 385.1. 1H NMR (300 MHz, DMSO-d6) delta 0.30-0.42 (2H, m), 0.53-0.66 (2H, m), 0.98-1.12 (1H, m), 1.24-1.35 (1H, m), 1.43-1.55 (1H, m), 2.39-2.46 (1H, m), 2.86-3.07 (3H, m), 7.19 (2H, d, J = 8.6 Hz), 7.53 (1H, t, J = 4.9 Hz), 7.75 (2H, d, J = 8.7 Hz), 8.11 (2H, d, J = 8.6 Hz), 8.53 (2H, d, J = 8.6 Hz), 8.97 (2H, d, J = 4.9 Hz), 9.06 (2H, brs), 10.37 (1H, s).

According to the analysis of related databases, 199678-12-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Takeda Pharmaceutical Company Limited; TOMITA, Naoki; KAJII, Shigeo; CARY, Douglas Robert; TOMITA, Daisuke; IMAMURA, Shinichi; TSUCHIDA, Ken; MATSUDA, Satoru; HARA, Ryujiro; EP2743256; (2014); A1;,
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Synthetic Route of 175277-33-5, Adding some certain compound to certain chemical reactions, such as: 175277-33-5, name is 4-(Dimethoxymethyl)-2-methylpyrimidine,molecular formula is C8H12N2O2, 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 175277-33-5.

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.

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. 175277-33-5, 4-(Dimethoxymethyl)-2-methylpyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; WARD, Richard, Andrew; GRAHAM, Mark, Andrew; SWALLOW, Steven; JONES, Clifford, David; (282 pag.)WO2016/162325; (2016); A1;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 313339-35-4, name is 4,6-Dichloro-2-(methylthio)pyrimidine-5-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 313339-35-4

3.0 g (12.55 mmol, 1.0 eq) of 4,6-dichloro-2-(methylthio)pyrimidine-5-carboxylic acid was dissolved in 40 mL of anhydrous toluene, to which 15 mL of thionyl chloride (SOCl2) was added, followed by stirring at 115 C. for 12 hours. The reaction solvent was concentrated under reduced pressure and dried to give acid chloride. Then, 1.6 g of 5-chloro-7-(methylthio)pyrimido[4,5-d]pyrimidine-4(1H)-one was prepared as a white solid according to the same manner as described in step 2 of Example 66 (2 step yield: 56%). 1H NMR (300 MHz, DMSO-d6) delta 2.56-2.58 (d, J=6.0, 3H), 8.42-8.44 (d, J=6.0, 1H), 12.88 (br s, 1H).

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, 313339-35-4, 4,6-Dichloro-2-(methylthio)pyrimidine-5-carboxylic acid.

Reference:
Patent; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; Lee, Ge Hyeong; Lim, Hee-Jong; Cho, Heeyeong; Park, Woo Kyu; Kim, Seong Hwan; Choi, Jung Hwan; (148 pag.)US2018/105527; (2018); A1;,
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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.1126-44-9, name is 2-Methylsulfanylpyrimidine-4-carboxylic acid, molecular formula is C6H6N2O2S, molecular weight is 170.189, as common compound, the synthetic route is as follows.Safety of 2-Methylsulfanylpyrimidine-4-carboxylic acid

The starting material 2-methylsulfanyl-pyrimidine-4-carboxylic acid methoxy-methyl-amide can be prepared as follows. Preparation of 2-methylsulfanyl-pyrimidine-4-carboxylic acid methoxy-methyl-amide: To a slurry of 2-methylsulfanyl-pyrimidine-4-carboxylic acid (10.0 g, 59.2 mmol) in CH3CN (300 mL) is added in sequence: I-hydroxybenzotriazole hydrate (9.59 g, 71.0 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (13.6 g, 71.0 mmol), N,O-dimethylhydroxylamine hydrochloride (8.66 g, 88.8 mmol), and triethylamine (Et3N) (24.9 mL, 178 mmol). The resulting slurry is stirred overnight at ambient temperature. After 16 hours, the reaction mixture is poured into a saturated aqueous solution of sodium bicarbonate (300 mL) and the layers separated. The aqueous layer is extracted with ethyl acetate (3×250 mL). The combined organic layers are washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo and the resulting residue is purified over silica (100% EtOAc) to afford 10.1 g (89% yield) of the desired product as a yellow oil. 1H NMR (300 MHz, CDCl3) delta 8.65 (d, J=4.9 Hz, 1H), 7.15 (br s, 1H), 3.77 (br s, 3H), 3.38 (br s, 3H), 2.61 (s, 3H); MS (ESI) m/z 214 (M+1).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1126-44-9, 2-Methylsulfanylpyrimidine-4-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; The Procter & Gamble Company; US2005/113392; (2005); A1;,
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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. 43088-67-1, name is 4-Chloro-5-methylthieno[2,3-d]pyrimidine, the common compound, a new synthetic route is introduced below. SDS of cas: 43088-67-1

Production Example 190. 4-(2-indanylamino)-5-methylthieno[2,3-d]pyrimidine 4-chloro-5-methylthieno[2,3-d]pyrimidine (92 mg, 0.50 mmol) (see J. Pharm. Soc. JAPAN, 109, 464 (1989)) and 2-aminoindan (330 mg, 2.5 mmol) in dry ethanol (1 ml) were heated to reflux under an argon atmosphere for 40 minutes. The solvent was distilled off under reduced pressure and the residue obtained was purified by silica gel chromatography (hexane: ethyl acetate = 5: 1) toobtain the title compound (140 mg, 0.50 mmol) having the following physical properties: 1H NMR (400 MHz, CDCl3): delta 2.47 (3H, s), 2.94 (2H, m), 3.50 (2H, m), 5.11 (1H, m), 5.65 (1H, br.), 6.80 (1H, s), 7.19-7.27 (4H, m), 8.47 (1H, s). MS (FAB): m/z 282 (M+H)+.

The synthetic route of 43088-67-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUNTORY LIMITED; EP1132093; (2001); A1;,
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Adding a certain compound to certain chemical reactions, such as: 3438-55-9, 5-Bromo-4-chloro-6-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, 3438-55-9, blongs to pyrimidines compound. SDS of cas: 3438-55-9

95-Bromo-6-methylpyrimidine-4-carbonitrile was prepared from 5-bromo-4-chloro-6-methylpyrimidine via reaction with potassium cyanide and l,4,7,l0,13,16-hexaoxacyclooctadecane. 4-Bromo-3-fluorophenol was converted to [3-fluoro-4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)phe- noxy][tri(propan-2-yl)]silane using the conditions outlined in footnote 5. These two reagents were subjected to Suzuki reaction and desilylation as described in footnote 5, affording 5-(2-fluoro-4-hydroxyphenyl)-6-methylpyrimidine-4-carbonitrile.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3438-55-9, its application will become more common.

Reference:
Patent; PFIZER INC; DAVOREN, JENNIFER ELIZABETH; DOUNAY, AMY BETH; EFREMOV, IVAN VIKTOROVICH; GRAY, DAVID LAWRENCE FIRMAN; MENTE, SCOT RICHARD; O’NEIL, STEVEN VICTOR; ROGERS, BRUCE NELSEN; SUBRAMANYAM, CHAKRAPANI; ZHANG, LEI; US2014/128374; (2014); A1;,
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