Pyrimidines

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. 1920-66-7, name is 4-Amino-2-chloro-5-nitropyrimidine, molecular formula is C4H3ClN4O2, 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. Recommanded Product: 1920-66-7

General procedure: The relevant halogenated heterocycle (1.0equiv.), substituted aniline (2.0 equiv.) and TFA (5.0 equiv.) were takenup in TFE (0.1 M) and heated under microwave irradiation conditionsat 140 C for 30 min before being concentrated in vacuo. The residuewas resuspended in EtOAc:THF (1:1, 20 mL/mmol), washed with saturatedNaHCO3 solution (20 mL/mmol), and the aqueous phase wasfurther extracted with EtOAc:THF (1:1, 3 × 15 mL/mmol). The combinedorganic extracts were washed with brine, dried (MgSO4) andconcentrated in vacuo. The resultant residue was purified via columnchromatography and/or triturated as specified to afford the desired compound.

With the rapid development of chemical substances, we look forward to future research findings about 1920-66-7.

Reference:
Article; Casalvieri, Kimberly A.; Matheson, Christopher J.; Backos, Donald S.; Reigan, Philip; Bioorganic and Medicinal Chemistry; vol. 28; 5; (2020);,
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Related Products of 22536-61-4, 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.22536-61-4, name is 2-Chloro-5-methylpyrimidine, molecular formula is C5H5ClN2, molecular weight is 128.56, as common compound, the synthetic route is as follows.

In a sealed glass tube a suspension of l-cyclopropyl-6-(lH-imidazol-5-yl)-3,3-dimethylindolin- 2-one (example 71a, 70 mg), 2-chloro-5-methylpyrimidine (37.0 mg) and cesium carbonate (158 mg) in acetonitrile (1.05 ml) was heated to 120 °C for 30 minutes under microwave irradiation. Then again 18 mg 2-chloro-5-methylpyrimidine and 89 mg cesium carbonate were added and the reaction mixture heated to 120°C under conventional heating for 2 hours. The reaction mixture was concentrated in vacuo and purified by flash chromatography (silica gel, gradient, 0percent to 100percent EtOAc in n-heptane). The title compound was obtained as off white solid (75 mg, 80percent). MS (ESI, m/z): 360.2 [(M+H)+].

Statistics shows that 22536-61-4 is playing an increasingly important role. we look forward to future research findings about 2-Chloro-5-methylpyrimidine.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; HILPERT, Hans; KOLCZEWSKI, Sabine; LIMBERG, Anja; STOLL, Theodor; WO2015/177110; (2015); A1;,
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Reference of 90905-33-2 ,Some common heterocyclic compound, 90905-33-2, molecular formula is C6H6N2O, 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.

4-chloro-N2-methylpyridine-2, 3-diamine (840 mg, 5.33 mmol) and iron (III) chloride hexahydrate (360 mg, 1.33 mmol) were dissolved in DMF (26 ml). 2-Methylpyrimidine-5-carbaldehyde (716 mg, 5.86 mmol) was then added and the reaction was allowed to stir vigorously at 80 open to air for 18 h The reaction mixture was then diluted with 3:. 1 chloroform: IPA and washed with water The combined organic layers. were washed with brine, dried over MgSO 4, and concentrated in vacuo while loading onto silica gel Purification by column chromatography. (silica gel, eluting with a gradient of 0 -60percent 3: 1 EtOAc: EtOH in hexanes) gave 7-chloro -3-ethyl-2- (2- methylpyrimidin-5-yl) -3H-imidazo [4, 5-b] pyridine (Intermediate IV). MS ESI calc’d. for C 13 H 13 ClN 5 [M + 1]+ 274; found 274.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,90905-33-2, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MCGOWAN, Meredeth Ann; ZHOU, Hua; KATZ, Jason D.; YANG, Lihu; METHOT, Joey; LIPFORD, Kathryn Ann; XU, Shimin; FU, Ning; XU, Guoquan; BIAN, Deqian; FU, Jianmin; LI, Yabin; FONG, Kin Chiu; (124 pag.)WO2017/125; (2017); A1;,
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Reference of 69034-12-4, 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. 69034-12-4, name is 2-Chloro-5-(trifluoromethyl)pyrimidine. A new synthetic method of this compound is introduced below.

Example 1.14: Preparation of 2-(4-(((lr,4r)-4-(5-(Methylsulfonyl)pyridin-2- yl)cyclohexyloxy)methyl)piperidin-l-yl)-5-(trifluoromethyl)pyrimidine (Compound 18).; To a dichloromethane (1 mL) solution of tert-butyl 4-(((lr,4r)-4-(5- (methylsulfonyl)pyridin-2-yl)cyclohexyloxy)methyl)piperidine-l-carboxylate (36 mg, 0.080 mmol), prepared in Example 1.13, Step B, was added a 4 M dioxane solution of hydrogen chloride (0.994 mL, 3.98 mmol). The reaction was stirred at 23 C for 30 min then concentrated. The residue was taken up in iPrOH (1.0 mL) and N-ethyl-N-isopropylpropan-2-amine (0.083 mL, 0.477 mmol). The resulting solution was divided into two equal portions. To one portion was added 2-chloro-5-(trifluoromethyl)pyrimidine (14.52 mg, 0.080 mmol). The reaction was stirred at 110 C for 40 min then concentrated. The residue was purified by preparative TLC (5% MeOH/CH2Cl2) to give the title compound (22.4 mg, 0.045 mmol, 113 % yield) as white solid. Exact mass calculated for C23H29F3N4O3S: 498.2, found: LCMS m/z = 499.5 [M+H]+; lU NMR (400 MHz, CDC13) delta ppm 1.18-1.26 (m, 2H), 1.34-1.44 (m, 2H), 1.60-1.70 (m, 2H), 1.85- 1.90 (m, 3H), 2.00-2.07 (m, 2H), 2.17-2.23 (m, 2H), 2.77-2.85 (m, 1H), 2.90-2.97 (m, 2H), 3.10 (s, 3H), 3.25-3.34 (m, 1H), 3.38 (d, = 6.0 Hz, 2H), 4.84-4.88 (m, 2H), 7.36 (d, = 8.2 Hz, 1H), 8.13 (dd, = 8.2 and 2.4 Hz, 1H), 8.46 (s, 2H), 9.05 (d, = 2.4 Hz, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,69034-12-4, its application will become more common.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; JONES, Robert M.; HAN, Sangdon; LEHMANN, Juerg; THORESEN, Lars; WO2012/135570; (2012); A1;,
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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. 33034-67-2, name is 2-Chloro-4-(trifluoromethyl)pyrimidine, molecular formula is C5H2ClF3N2, 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. name: 2-Chloro-4-(trifluoromethyl)pyrimidine

4-(2-Bromophenyl)piperazine-1-carboxylic acid tert-butyl ester (280 mg, 0.82 mmol),4,6-Dimethylpyrimidin-2-amine (151 mg, 1.23 mmol),Sodium tert-butoxide (0.16 g, 1.16 mmol), tris(dibenzylideneacetone) dipalladium (75 mg, 0.082 mmol) and(±)-2,2′-bis-(diphenylphosphino)-1,1′-binaphthyl (102 mg, 0.164 mmol) was added to anhydrous tolueneIn (20 mL), the reaction was heated to 120 C for 12 hours under a nitrogen atmosphere. The reaction was stopped, and the mixture was cooled to room temperature. The mixture was poured into water (100 mL), ethyl acetate (40 mL×3), and the organic phase was combined and washed with water (50 mL) and brine (50 mL) Dry and distill off the solvent under reduced pressure.The obtained crude product was subjected to column chromatography (dichloromethane:methanol (V:V)=50:1)The title compound (white solid, 274 mg, 87%)

With the rapid development of chemical substances, we look forward to future research findings about 33034-67-2.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jin Chuanfei; Zhang Yingjun; Xue Yaping; Guo Zhengjiang; (39 pag.)CN109912514; (2019); A;,
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Electric Literature of 111196-81-7, 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.111196-81-7, name is 2-Chloro-5-ethylpyrimidine, molecular formula is C6H7ClN2, molecular weight is 142.59, as common compound, the synthetic route is as follows.

Step B: Preparation of 5-Ethyl-2-(4-(((lr,4r)-4-(2-fluoro-4- (methylsulfonyl)phenyl)cyclohexyloxy)methyl)piperidin-l-yl)pyrimidine (Compound 8).; A mixture of 4-(((lr,4r)-4-(2-fluoro-4- (methylsulfonyl)phenyl)cyclohexyloxy)methyl)piperidine hydrochloride (50.4 mg, 0.124 mmol), prepared in Step A above, 2-chloro-5-ethylpyrimidine (36 mu, 0.296 mmol), and triethylamine (52 mu, 0.373 mmol) in iPrOH (3 mL) was heated under microwave irradiation at 120 C for 2 h. The mixture was extracted with water and AcOEt. The organic phase was dried over MgS04, filtered, and concentrated. The residue was purified by silica gel flash column chromatography (hexane/ AcOEt gradient). Fractions containing the title compound (with 2- chloro-5-ethylpyrimidine as by product) were partly concentrated. The residue was treated with MTBE. Solid was filtered off, washed with additional MTBE, and dried under high vacuum to give the title compound (35.6 mg, 0.075 mmol, 60.3 % yield) as a white solid. Exact mass calculated for C25H34FN3O3S: 475.23, found: LCMS m/z = 476.2 [M+H]+; lU NMR (400 MHz, CDCI3) delta ppm 1.16-1.23 (m, 5H), 1.39-1.55 (m, 4H), 1.83-1.86 (m, 3H), 1.92-1.95 (m, 2H), 2.17-2.20 (m, 2H), 2.44 (q, = 7.6 Hz, 2H), 2.84-2.91 (m, 3H), 3.27 (s, 3H), 3.25-3.29 (m, 1H), 3.36 (d, = 6.1 Hz, 2H), 4.70-4.73 (m, 2H), 7.39-7.43 (m, 1H), 7.57-7.60 (m, 1H), 7.66-7.68 (m, 1H), 8.16 (s, 2H).

Statistics shows that 111196-81-7 is playing an increasingly important role. we look forward to future research findings about 2-Chloro-5-ethylpyrimidine.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; JONES, Robert M.; HAN, Sangdon; LEHMANN, Juerg; THORESEN, Lars; WO2012/135570; (2012); A1;,
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Application of 302964-08-5, 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. 302964-08-5, name is 2-((6-Chloro-2-methylpyrimidin-4-yl)amino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide, molecular formula is C16H13Cl2N5OS, 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 mixture of the starting material 7H (150 mg, 0.38 mmol) and dioxane (8 mL) were added (S)-pyrrolidin-3-ol hydrochloride (141 mg, 1.14 mmol, 3 eq) and DIEA (245 mg, 1.90 mmol, 5 eq) at room temperature. The mixture was then stirred at 90-92 C. under nitrogen for 12 h. LC-MS analysis showed the product peak. The mixture was not a clear solution. The mixture was cooled to room temperature and concentrated to dryness under reduced pressure, and the resultant residue was suspended in 50 mL acetonitrile, and centrifuged at 4000 rpm for 15 min. The pellet was then suspended in cooled 80% acetonitrile, and centrifuged at 4000 rpm for 15 min. The pellet was re-suspended in cooled 80% acetonitrile, and centrifuged at 4000 rpm for 15 min. The supernatants were combined and concentrated to dryness to afford the target compound X (H-31) (105 mg) as an off-white solid. LC-MS: 445 (M+H); 1H NMR (DMSO-d6): 11.40 (s, 1H. NH), 9.83 (s, 1H, NH), 8.19 (s, 1H), 7.40 (m, 1H), 7.24 (m, 2H), 5.80 (s, 1H), 4.98 (s, 1H), 4.35 (s, 1H), 2.53 (s, 3H), 2.20 (s, 2H), 2.12 (s, 2H), 1.85 (m, 2H).

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 302964-08-5, 2-((6-Chloro-2-methylpyrimidin-4-yl)amino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide.

Reference:
Patent; Princeton Drug Discovery Inc; He, Kan; (37 pag.)US2018/99960; (2018); A1;,
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Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 347418-42-2, 4-Chloro-5-fluoropyrimidine, 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, Safety of 4-Chloro-5-fluoropyrimidine, blongs to pyrimidines compound. Safety of 4-Chloro-5-fluoropyrimidine

The compound 5 (1 mmol),The compound 4-chloro-5-fluoropyrimidine (1 mmol)Dissolved in NMP (10 mL)CuI (20 mmol%) was added,Pd (PPh3) 2Cl2 (5 mmol%),DIEA (5 mmol).Under nitrogen protection,60 reaction 12h.TCL monitoring reaction is complete,Extracted three times with ethyl acetate,Combine organic phase,Washed twice with saturated NaCl,Anhydrous Na2SO4 dry.Spin dry,Column chromatography gave compound 7r.

The synthetic route of 347418-42-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Second Military Medical University, PLA; Yantai Dongcheng Pharmaceutical Industry Group Co., Ltd.; Zhang, Dazhi; Jiang, Yuanying; Niting, Junhong; Cai, Zhan; Pang, Lei; Xie, Fei; Li, Ran; Han, Haibing; He, Yan; You, Shouyi; Yang, Zhenqiu; Qi, Dongqi; (36 pag.)CN106336383; (2017); A;,
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Electric Literature of 767-15-7, 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 767-15-7, name is 2-Amino-4,6-dimethylpyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: For the synthesis of 2, the solution of sulfurisocyanatidic chloride (7.2mmol) in 20mL toluene was added to the solution of 1 (6.0mmol) in 20mL toluene dropwise at room temperature. The reactant was heated to 140C and then the reaction proceeded for 18h under reflux. Subsequently, the mixture was cooled down to room temperature and remaining sulfurisocyanatidic chloride was removed under reduced pressure, together with the solvent. Without further purification, the resulting yellow oil 2 was dissolved in 10mL anhydrous acetonitrile and after that it was added slowly to 5mmol of 3, which was also dissolved in 10mL anhydrous acetonitrile beforehead in ice bath. After stirring for 24hat room temperature, acetonitrile was removed under reduced pressure and saturated sodium bicarbonate was added to product 4. Product 5 precipitated easily and it was further purified by recrystallization from petroleum ether/acetone in 1:1 ratio in high yields. 15% hydrochloric acid was added to aqueous solution of 5 under stirring and corresponding acidified product 4 precipitated out easily in high yields.

According to the analysis of related databases, 767-15-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wu, Ren-Jun; Ren, Tongtong; Gao, Jie-Yu; Wang, Li; Yu, Qilin; Yao, Zheng; Song, Guo-Qing; Ruan, Wei-Bin; Niu, Cong-Wei; Song, Fu-Hang; Zhang, Li-Xin; Li, Mingchun; Wang, Jian-Guo; European Journal of Medicinal Chemistry; vol. 162; (2019); p. 348 – 363;,
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Synthetic Route of 939986-65-9, Adding some certain compound to certain chemical reactions, such as: 939986-65-9, name is 6-Chloropyrimidine-4-carbonitrile,molecular formula is C5H2ClN3, 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 939986-65-9.

A solution of 4-(hydroxymethyl)-1H-indazole 1 (233 mg, 1.57 mmol), 6-chloropyrimidine-4-carbonitrile (200 mg, 1.43 mmol), and DMF (4 mL) was added dropwise at RT to NaH (57 mg of a 60% dispersion in mineral oil, 1.43 mmol). The mixture was stirred at RT for 25 mm. The mixture was partitioned between aq HC1, brine, and EtOAc. The organic layer was separated, dried (Na2504), filtered, and concentrated under reduced pressure. The residue was purified (silica gel; eluting 0 to 100% EtOAc in hexanes), to afford compound 2 (162 mg, 45%) as a yellow solid. LCMS Mass: 252.0 (M+1).

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. 939986-65-9, 6-Chloropyrimidine-4-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PHARMAKEA, INC.; ROWBOTTOM, Martin, W.; HUTCHINSON, John, Howard; (185 pag.)WO2017/3862; (2017); A1;,
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