Category: 3167-50-8

Synthetic Route of 3167-50-8 ,Some common heterocyclic compound, 3167-50-8, molecular formula is C5H5N3O2, 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 solution of 2-(2-methyl-1H-indol-1-yl)ethanamine (4a) (65 mg, 0.373 mmol) and 4-(piperidin-1-yl)benzoic acid (5) (76 mg, 1 eq.), and dimethylaminopyridine (catalytic, ?5 mg) in dichloromethane (6 mL) was added 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide.hydrochloride (EDCI) (92 mg, 1.3 eq.) at room temperature. The resulting reaction mixture was stirred for 6h. At the conclusion of the reaction (TLC), water (15 mL) was added to quench the reaction. The product was extracted with ethyl acetate (20mL×3). Organics were washed with dilute HCl (10 mL), saturated NaHCO3 solution (10 mL), water (10 mL) and brine solution (10 mL) and dried over Na2SO4 and concentrated. The resulting crude product was subjected to silica gel chromatography eluting with 0-40% ethyl acetate in hexane to furnish 7k (TG7-152) (100mg, 74% yield). 1H NMR (CDCl3): delta 7.52 (d, J=5.6Hz, 1H), 7.49 (d, J=8.8Hz, 2H), 7.30 (d, J=8Hz, 1H), 7.07 (m, 2H), 6.80 (d, J=8.2Hz, 2H), 6.23 (s, 1H), 5.98 (t, J=5.4Hz, 1H), 4.33 (t, J=6Hz, 2H), 3.76 (q, J=6Hz, 2H), 3.25 (t, J=4.8Hz, 4H), 2.37 (s, 3H), 1.6 (m, 6H). LCMS (ESI): >97% purity at lambda 254, MS; m/z, 362 [M+H]+. Anal. Calcd. for C23H27N3O: C, 76.42; H, 7.53; N, 11.62; found; C, 76.48; H, 7.55; N, 11.59.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3167-50-8, its application will become more common.

Reference:
Article; Ganesh, Thota; Jiang, Jianxiong; Dingledine, Ray; European Journal of Medicinal Chemistry; vol. 82; (2014); p. 521 – 535;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 3167-50-8, 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. 3167-50-8, name is 2-Aminopyrimidine-5-carboxylic acid, molecular formula is C5H5N3O2, 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 100mL one-neck flask,2-amino-5-pyrimidinyl acid (1.39g, 10.0mmol) was dissolved in DMF (25mL), wasadded 1- (3-dimethylaminopropylAminopropyl) -3-ethylcarbodiimidehydrochloride (191mg, 1.0mmol) and triethylamine (0.42mL, 3.0mmol), stirred for10min, add1 -tert-butoxycarbonyl-piperazine (135mg,1.0mmol), the reaction at room temperature 12h. The organic solvent wasdistilled off under reduced pressure, the residue was purified by columnchromatography (twoDichloromethane / methanol (V / V) = 10/1),to give a pale yellow oil (1.25g, 56.60%).

According to the analysis of related databases, 3167-50-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; East Sunshine Pharmaceutical Co., Ltd.; Liu, Bing; Zhang, Yingjun; Nie, Linlin; Bai, Shun; Zheng, Changchun; Nie, biao; Li, Zhiyong; Tan, Yumei; (61 pag.)CN105294737; (2016); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 3167-50-8, 2-Aminopyrimidine-5-carboxylic acid, 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, category: pyrimidines, blongs to pyrimidines compound. category: pyrimidines

To 1.9 g of polyphosphoric acid were added 500 mg (3.59 mmol) of 2-aminopyrimidine-5-carboxylic acid portionwise. It was stirred for 5 mm before 327.6 mg (3.59 mmol) of hydrazinecarbothioamide were added portionwise. It was stirred for 1 h at 140 C. It was allowed to cool down and water was added. The pH was adjusted to 12 by adding 25 vol% aqueous ammonia solution. The precipitate wasfiltered off and washed with water. It was dried under vacuum at 50 C to yield 164 mg (23%) of the title compound, containing ca. 25 mol% of the starting material.?H-NMR (300MHz, DMSO-d6): 6 [ppm]= 7.13 (s, 2H), 7.30 (s, 2H), 8.56 (s, 2H).LC-MS (Method 3): R = 0.44 mm; MS (ESIpos): m/z = 195 [M+H].

At the same time, in my other blogs, there are other synthetic methods of this type of compound,3167-50-8, 2-Aminopyrimidine-5-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; THEDE, Kai; BENDER, Eckhard; SCOTT, William; RICHTER, Anja; ZORN, Ludwig; LIU, Ningshu; MOeNNING, Ursula; SIEGEL, Franziska; GOLZ, Stefan; HAeGEBARTH, Andrea; LIENAU, Philip; PUEHLER, Florian; BASTING, Daniel; SCHNEIDER, Dirk; MOeWES, Manfred; GEISLER, Jens; WO2015/140195; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia