69034-12-4 | Pyrimidines

Share a compound : 2-Chloro-5-(trifluoromethyl)pyrimidine

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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. 69034-12-4, name is 2-Chloro-5-(trifluoromethyl)pyrimidine. A new synthetic method of this compound is introduced below., COA of Formula: C5H2ClF3N2

Example 44k (300 mg, 0.8 mmol), 2-Chloro-5-(trifluoromethyl)pyrimidine (199 mg, 1.09 mmol) and N,N-diisopropylethylamine (287 mul, 1.67 mmol) are dissolved in 4 ml of anhydrous DMSO and heated in a microwave reactor during 30 minutes at 150C. The crude is partitioned between EtOAc and water, the organic layer is dried over anhydrous Na2S04 then concentrated under reduced pressure to obtain 360 mg of the title product. HPLC-MS (Method 10): Rt = 3. MS (ES+): m/z = 505 [M+H]+ . The enantiomers are obtained by HPLC using a chiral stationary phase. Method for separation: HPLC apparatus type: Waters 600 Pump; column: Daicel Chiralpack AD-H, 5.0 muiotaeta, 250 mm x 20 mm; method: eluent hexane/ IPA 70:30; flow rate: 15 mL/min, Temperature: 25 C; UV Detection: 254 nm Example of separation by chiral HPLC: Submitted to separation: 665 mg of Example 1 prepared as described above; Obtained: 157 mg of enantiomer 1 (Exp. 2) and 40 mg of enantiomer 2 (Exp. 3).

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HOENKE, Christoph; GIOVANNINI, Riccardo; LESSEL, Uta; ROSENBROCK, Holger; SCHMID, Bernhard; WO2015/55698; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

17-Sep News The origin of a common compound about 69034-12-4

Statistics shows that 69034-12-4 is playing an increasingly important role. we look forward to future research findings about 2-Chloro-5-(trifluoromethyl)pyrimidine.

Synthetic Route of 69034-12-4, 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.69034-12-4, name is 2-Chloro-5-(trifluoromethyl)pyrimidine, molecular formula is C5H2ClF3N2, molecular weight is 182.531, as common compound, the synthetic route is as follows.

A mixture of crude methyl 4-ethyl- 1,2,3 ,4-tetrahydroi soquinoline-7-carboxyl ate (100 mg, 0.46 mmol), 2-chloro-5-(trifluoromethyl)pyrimidine (99 mg, 0.55 mmol) and DIPEA (178 mg, 1.38 mmol) in CH3CN (1 mL) was stirred at 100 C for 2 h in a sealed tube. LCMS showed that the reaction was completed. The mixture was concentrated under reduced pressure. The residue was purified by preparative TLC with petroleum ether ethyl acetate = 81 to afford methyl 4-ethyl-2-(5 -(trifluoromethyl)pyrimidin-2-yl)- 1,2,3 ,4-tetrahydroi soquinoline-7- carboxylate (140 mg, 81.8%) as a yellow oil. LC-MS tR= 0.911 mm in 5-95AB 1.5 mm chromatography (Welch IVIK RP-18e, 25-2 mm), MS (ESI) mz 366.0 [M+H].

Statistics shows that 69034-12-4 is playing an increasingly important role. we look forward to future research findings about 2-Chloro-5-(trifluoromethyl)pyrimidine.

Reference:
Patent; VITAE PHARMACEUTICALS, INC.; CLAREMON, David, A.; DILLARD, Lawrence, Wayne; FAN, Yi; JIA, Lanqi; SINGH, Suresh, B.; TICE, Colin, M.; XU, Zhenrong; YUAN, Jing; ZHUANG, Linghang; (172 pag.)WO2017/87608; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Sep-21 News Some scientific research about 69034-12-4

Statistics shows that 69034-12-4 is playing an increasingly important role. we look forward to future research findings about 2-Chloro-5-(trifluoromethyl)pyrimidine.

Electric Literature of 69034-12-4, 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.69034-12-4, name is 2-Chloro-5-(trifluoromethyl)pyrimidine, molecular formula is C5H2ClF3N2, molecular weight is 182.531, as common compound, the synthetic route is as follows.

General procedure: To a solution of 25a (200 mg, 0.458 mmol) in NMP (4 ml)was added 2-chloro-5-(trifluoromethyl)pyrimidine (100 ng,0.549 mmol) and K2CO3 (189 mg, 1.374 mmol) at room temperature.The reaction mixture was heated at 90 C for 3 h. After cooling to room temperature, the reaction mixture was diluted with water.The aqueous layer was separated and then extracted with EtOAc. The combined organic extracts were washed with water and brine,dried over Na2SO4, filtered, and concentrated. The residue was purified by flash column chromatography (silica gel: CHCl3/MeOH = 95/5) to afford 26a

Statistics shows that 69034-12-4 is playing an increasingly important role. we look forward to future research findings about 2-Chloro-5-(trifluoromethyl)pyrimidine.

Reference:
Article; Tsuno, Naoki; Yukimasa, Akira; Yoshida, Osamu; Suzuki, Shinji; Nakai, Hiromi; Ogawa, Tomoyuki; Fujiu, Motohiro; Takaya, Kenji; Nozu, Azusa; Yamaguchi, Hiroki; Matsuda, Hidetoshi; Funaki, Satoko; Yamanada, Natsue; Tanimura, Miki; Nagamatsu, Daiki; Asaki, Toshiyuki; Horita, Narumi; Yamamoto, Miyuki; Hinata, Mikie; Soga, Masahiko; Imai, Masayuki; Morioka, Yasuhide; Kanemasa, Toshiyuki; Sakaguchi, Gaku; Iso, Yasuyoshi; Bioorganic and Medicinal Chemistry; vol. 25; 7; (2017); p. 2177 – 2190;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

10 Sep 2021 News The origin of a common compound about 69034-12-4

According to the analysis of related databases, 69034-12-4, the application of this compound in the production field has become more and more popular.

Reference of 69034-12-4, Adding some certain compound to certain chemical reactions, such as: 69034-12-4, name is 2-Chloro-5-(trifluoromethyl)pyrimidine,molecular formula is C5H2ClF3N2, 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 69034-12-4.

Example 1.37: Preparation of 4-((lr,4r)-4-((l-(5-(Trifluoromethyl)pyrimidin-2-yl)piperidin- 4-yl)methoxy)cyclohexyl)nicotinonitrile (Compound 59).; A mixture of 4-((lr,4r)-4-(piperidin-4-ylmethoxy)cyclohexyl)nicotinonitriledihydrochloride (27 mg, 72.52 muetaiotaomicron), 2-chloro-5-(trifluoromethyl)pyrimidine (0.03 ml, 0.164 mmol), and potassium carbonate (50 mg, 0.362 mmol) in 1 ml iPrOH was heated under micorwave irradiation at 85C for 2 h. Mixture was purified by HPLC (CH3CN/H20 gradient + 0.1% TFA). Fractions containing desired product were partly concentrated and residue was extracted with 1 M NaOH and CH2C12. Organic phases were dried over MgS04, filtered, and concentrated to give 4-((lr,4r)-4-((l-(5-(trifluoromethyl)pyrimidin-2-yl)piperidin-4- yl)methoxy)cyclohexyl)nicotinonitrile (14.6 mg, 32.77 muetaiotaomicron, 45.2 %) as a white solid. Exact mass calculated for C23H26F3N50: 445.21, found: LCMS m/z = 446.4 (M+H+); lU NMR (400 MHz, CDC13) delta ppm 1.17-1.28 (m, 2H), 1.41-1.62 (m, 4H), 1.85-2.04 (m, 5H), 2.18-2.24 (m, 2H), 2.90-2.99 (m, 3H), 3.26-3.33 (m, 1H), 3.38 (d, = 6.0 Hz, 2H), 4.84-4.90 (m, 2H), 7.28 (d, = 5.3 Hz, 1H), 8.47 (s, 2H), 8.80 (d, = 5.3 Hz, 1H), 8.81 (s, 1H).

According to the analysis of related databases, 69034-12-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; JONES, Robert M.; HAN, Sangdon; LEHMANN, Juerg; THORESEN, Lars; WO2012/135570; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

3 Sep 2021 News Analyzing the synthesis route of 69034-12-4

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.

Application 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 37(S)-5-(1 -Methanesulfonyl-1 ,2,3,6-tetrahvdro-pyridin-4-yl)-2-methyl-2-ri -(5- trifluoromethyl-pyridin-2-yl)-piperidin-4-yl1-2,3-dihvdro-furo[2,3-clpyridineThe title compound is prepared from (S)-5-(1 -methanesulfonyl-1 ,2,3,6-tetrahydro- pyridin-4-yl)-2-methyl-2-piperidin-4-yl-2,3-dihydro-furo[2,3-c]pyridine (Intermediate 41 ; the configuration of the stereocenter is arbitrarily assigned) and 2-chloro-5- (trifluoromethyl)pyridine in dimethylsulfoxide at 100C in the presence of potassium carbonate. LC (method 4): tR = 1 .04 min; Mass spectrum (EST): m/z = 523 [M+H]+.

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; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HIMMELSBACH, Frank; LANGKOPF, Elke; NOSSE, Bernd; WO2012/98217; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

3 Sep 2021 News Analyzing the synthesis route of 69034-12-4

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; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HIMMELSBACH, Frank; LANGKOPF, Elke; NOSSE, Bernd; WO2012/98217; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

02/9/2021 News New learning discoveries about 69034-12-4

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. 69034-12-4, 2-Chloro-5-(trifluoromethyl)pyrimidine, other downstream synthetic routes, hurry up and to see.

Related Products of 69034-12-4 ,Some common heterocyclic compound, 69034-12-4, molecular formula is C5H2ClF3N2, 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.

Sep 2021 News Simple exploration of 69034-12-4

STEP 2A: 2-[(3R)-3-METHYLPIPERAZIN-1-YL]-5-(TRIFLUOROMETHYL)PYRIMIDINE (0208) To a solution of tert-butyl (2R)-2-methylpiperazine-l-carboxylate (2.2 g, 11.0 mmol, 1.0 eq) and 2-chloro-5-(trifluoromethyl)pyrimidine (2.0 g, 11.0 mmol, 1.0 eq) in 1 -methyl-2-pyrrolidone (NuMuRho,IotaOmicron mL) was added N^V-diisopropylethylamine (5.7 mL, 44.0 mmol, 4.0 eq) and the reaction mixture heated to 100 C for 1 hr. The reaction mixture was cooled, diluted heavily with EtOAc, and washed repeatedly with brine (5x). The organic layer was dried over Na2SC>4 and concentrated. Silica gel column (80 g) was loaded using methylene chloride and run using an increasing gradient of EtOAc (5-90%) in hexanes over 20 min. The chromatographed material was dissolved in dioxane (25 mL) and treated with a solution of 4M HC1 in dioxane (6 mL). The resulting thick white suspension was concentrated, dissolved in MeOH, and made basic with the addition of MP-carbonate. Following removal of the resin and concentration of the filtrate, the free base of 2-[(3R)-3-methylpiperazin-l-yl]-5- (trifluoromethyl)pyrimidine 2a (1.9 g, 7.6 mmol, 69% over two steps) was isolated as a white solid.

Reference:
Patent; NEUROCRINE BIOSCIENCES, INC.; HARRIOTT, Nicole; PAGANO, Nicholas; (135 pag.)WO2017/79641; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Analyzing the synthesis route of 2-Chloro-5-(trifluoromethyl)pyrimidine

At the same time, in my other blogs, there are other synthetic methods of this type of compound,69034-12-4, 2-Chloro-5-(trifluoromethyl)pyrimidine, and friends who are interested can also refer to it.

Electric Literature 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.

A mixture of (R)-5-(1-methanesulfonyl-1,2,3,6-tetrahydro-pyridin-4-yl)-2-piperidin-4-yl-2,3-dihydro-furo[2,3-c]pyridine (Intermediate 39, the configuration of the stereocenter is arbitrarily assigned; 110 mg}, 2-chloro-5-trifluoromethyl-pyrimidine (76 mg), K2CO3 (100 mg), and dimethyl sulfoxide (1.5 mL) is stirred at 110 C. for 3 h. After cooling to room temperature, water is added and the resulting mixture is extracted with ethyl acetate. The combined extracts are washed with brine, dried (Na2SO4), and concentrated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 30:70?10:90) to give the title compound. LC (method 5): tR=1.32 min; Mass spectrum (ESI+): m/z=510 [M+H]+.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HIMMELSBACH, Frank; LANGKOPF, Elke; NOSSE, Bernd; US2013/18030; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Extended knowledge of 2-Chloro-5-(trifluoromethyl)pyrimidine

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. 69034-12-4, name is 2-Chloro-5-(trifluoromethyl)pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C5H2ClF3N2

N,N-Diisopropylethylamine (30 mu, 0.2 mmol) is added to a stirred solution of example 62a (35 mg, 0.2 mmol) and 2-Chloro-5-(Trifluoromethyl)pyrimidine (36 mg, 0.2 mmol) dissolved in 1 ml of anhydrous DMSO; the reaction is heated in a microwave reactor during 2 hours at 100 C. Water and EtOAc are added to the crude, the organic phase is separated, washed with water, dried and concentrated under reduced pressure. The residue is purified by Silica gel flash chromatography, using DCM/MeOH 100:2 as eluent, to obtain the title compound (30 mg, 47% yield). UPLC-MS (Method 1): Rt = 0.90 min MS (ES+): m/z = 327 [M+H]+ . Chiral HPLC (Method 15): Rt = 4.38 min