Adding a certain compound to certain chemical reactions, such as: 6320-39-4, 3-Amino-4-hydroxypyridine, 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, Quality Control of 3-Amino-4-hydroxypyridine, blongs to pyridine-derivatives compound. Quality Control of 3-Amino-4-hydroxypyridine
To a large screw cap vial was added 3-aminopyridin-4-ol (0.440 g, 4.0 mmol) in DMF (lOmL) along with triethylamine (1.561 mL, 1 1.2 mmol), -(tert- butoxycarbonylamino)cyclopropanecarboxylic acid (0.845 g, 4.2 mmol) and finally TBTU, o-Benzotriazol-l-yl-N,N,N’,N’-tetramethyluronium tetrafluoroborate (1.605 g, 5.0 mmol). The vial was sealed and the brown mixture was shaken for 24 hours at room temperature. The reaction mixture was concentrated to an oil, taken up in acetonitrile and purified using a Shimadzu preparative HPLC employingacetonitrile/water/ammonium acetate where solvent A was 5% acetonitrile / 95% water / 10 mM ammonium acetate and solvent B was 5% water / 95% acetonitrile / 10 mM ammonium acetate with a Phenomenex-Luna IotaOmicronmuiotaeta C18 30x100mm column at a gradient of 0-100% B and a flow rate of 30mL/min. over 10 minutes with a 5 minute hold. Solvent was removed giving l.Ogram (81% yield) of tert-butyl l-(4- hydroxypyridin-3-ylcarbamoyl) cyclopropyl carbamate as a light yellow solid. The LC/MS data was obtained on a Shimadzu analytical LC /Micromass Platform LC (ESI+) at 220nm using the following set of conditions: Phenomenex Luna 3muetaiota CI 8, 2 x 50mm column, with a gradient of 0-100%B (B = 90% HPLC grade acetonitrile/ 0.1% trifluoroacetic acid/ 10% HPLC grade water), (A = 90% HPLC grade water / 0.1% trifluoroacetic acid/ 10% HPLC grade acetonitrile), in 4 minutes with a 1 minute hold at a rate of 0.8 mL/minute. HPLC purity was determined using a Shimadzu analytical LC at 254nm and 256nm with a Waters Sunfire CI 8 3.5muiotaeta 4.6 x 150mm column employing water/acetonitrile/ 0.1% trifluoroacetic acid with a gradient of 10-100% B (B = 95% HPLC grade acetonitrile/ 0.1% trifluoroacetic acid/ 5% HPLC grade water), (A = 95% HPLC grade water / 0.1% trifluoroacetic acid/ 5% HPLC grade acetonitrile), in 10 minutes with a 10 minute hold at a rate of 1 mL/minute. The HPLC purity was then confirmed with an orthogonal solvent system and column using a Shimadzu analytical LC with a Phenomenex Gemini CI 8 3.0muiotaeta 4.6 x 150mm column employing water/methanol/ lOmM ammonium bicarbonate with a gradient of 10-100%) B (B = 95% HPLC grade methanol/ lOmM ammonium bicarbonate / 5% HPLC grade water), (A = 95% HPLC grade water / lOmM ammonium bicarbonate / 5% HPLC grade methanol), in 10 minutes with a 10 minute hold at a rate of 1 mL/minute. XH NMR (400 MHz, CD3OD) delta ppm 1.17 (m, 2 H), 1.51 (s, 9 H), 1.59 (m, 2 H), 6.55 (d, J=7.03 Hz, 1 H), 7.74 (dd, J=7.03, 1.51 Hz, 1 H), 7.79 (br. s., 1 H), 8.89 (d, 1 H). LCMS rt =1.682, min., m/z 294.3(M + H). HPLC rt = 5.621min. (Sunfire C18), 94.9% purity and 7.961min. (Gemini C18), 100 % purity
At the same time, in my other blogs, there are other synthetic methods of this type of compound,6320-39-4, 3-Amino-4-hydroxypyridine, and friends who are interested can also refer to it.
Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; YEUNG, Kap-Sun; GRANT-YOUNG, Katharine, A.; KADOW, John, F.; WO2011/112769; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem