A new synthetic route of 6320-39-4

According to the analysis of related databases, 6320-39-4, the application of this compound in the production field has become more and more popular.

Related Products of 6320-39-4, 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 6320-39-4, name is 3-Amino-4-hydroxypyridine. This compound has unique chemical properties. The synthetic route is as follows.

Example 113-(1-[1,3]oxazolo[4,5-c]pyridin-2-ylpyrrolidin-3-yl)-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]propanenitrile (One Enantiomer Isolated) A solution of 3-aminopyridin-4-ol (0.250 g, 2.27 mmol, Bosche Scientific) and potassium O-ethyl dithiocarbonate (0.400 g, 2.50 mmol) in ethanol (1 mL) was heated to reflux. When the reaction was determined complete, it was cooled to ambient temperature and partitioned between 1N HCl and ethyl acetate. The organic layer was washed with water, dried over sodium sulfate, decanted and concentrated. This crude product was dissolved in toluene (6 mL) and thionyl chloride (0.365 mL, 5.01 mmol) followed by DMF (3 microL) was added. The mixture was heated to reflux for 1 h, cooled and the solvent removed in vacuo. A portion of this crude product (14 mg) was dissolved in 1,4-dioxane (0.40 mL), along with 3-pyrrolidin-3-yl-3-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]propanenitrile (20.0 mg, 0.0457 mmol, enantiomer 2 from Example 9, Step 2b), and N,N-diisopropylethylamine (16 microL, 0.091 mmol) was added. The mixture was heated to 70 C. for 1.5 h. The solvent was removed in vacuo and the residue was sequentially stirred with 50% TFA/DCM for 1.5 h, concentrated, and stirred with 0.3 mL EDA in methanol for 30 min. Purification via preparative-HPLC/MS (C18 column eluting with a gradient of ACN/H2O containing 0.15% NH4OH) afforded product. 1H NMR (400 MHz, d6-DMSO): delta 8.89 (s, 1H), 8.68 (s, 1H), 8.44 (s, 1H), 8.11 (dd, 1H), 7.72 (dd, 1H), 7.60 (d, 1H), 6.99 (d, 1H), 6.96 (dd, 1H), 4.88 (dt, 1H), 3.90 (dd, 1H), 3.71-3.63 (m, 1H), 3.58-3.30 (m, 4H), 3.04-2.93 (m, 1H), 1.80-1.66 (m, 2H); LCMS (M+H)+: 426.1.

According to the analysis of related databases, 6320-39-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Rodgers, James D.; Shepard, Stacey; Arvanitis, Argyrios G.; Wang, Haisheng; Storace, Louis; Folmer, Beverly; Shao, Lixin; Zhu, Wenyu; Glenn, Joseph; US2010/298334; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem