Introduction of a new synthetic route about 5-Bromo-N2-methylpyridine-2,3-diamine

The synthetic route of 89415-54-3 has been constantly updated, and we look forward to future research findings.

Adding a certain compound to certain chemical reactions, such as: 89415-54-3, 5-Bromo-N2-methylpyridine-2,3-diamine, 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, Formula: C6H8BrN3, blongs to pyridine-derivatives compound. Formula: C6H8BrN3

Step 3. 5-bromo-N3-isopropyl-N2-methylpyridine-2.3-diamine and 6-bromo-2,2,3-trimethyl-2.3-dihydro- 1H-imidazor4.5-blpyridine; 5-bromo-N2-methylpyridine-2,3-diamine (54.4 mg, 0.269 mmol) was dissolved in isopropyl acetate (1.5 ml) and acetone (23 mul, 0.31 mmol), trifluoroacetic acid (0.045 ml, 0.58 mmol), and sodium triacetoxyborohydride (64 mg, 0.30 mmol) were added. The reaction was stirred under nitrogen at room temperature for 4 hours, and then more acetone was added (0.040 ml) along with TFA (0.090 ml) and isopropyl acetate (0.5 ml). The reaction was then stirred overnight. This reaction was repeated on a larger scale using 5-bromo-N2-methylpyridine-2,3-diamine (288 mg, 1.43 mmol), 2,2,2-trifluoroacetic acid (0.30 ml, 3.9 mmol), acetone (0.13 ml, 1.8 mmol), and sodium triacetoxyborohydride (352 mg, 1.66 mmol). Then, both reactions were poured into water (25 ml), and solid sodium hydroxide was added to raise the pH to about 10. The layers were separated, and the aqueous phase was extracted with EtOAc. The organic extracts were combined, dried over sodium sulfate, filtered, concentrated, and dried under high vacuum. To afford 5-bromo-N3-isopropyl-N2-methylpyridine-2,3-diamine and 6-bromo-2,2,3- trimethyl-2,3-dihydro-1H-imidazo[4,5-b]pyridine (399 mg, 97% combined yield). 5-bromo-N3-isopropyl-N2-methylpyridine-2,3-diamine: MS (ESI pos. ion) m/z: 244 (MH+, 79Br), 246 (MH+, 81Br). Calculated exact mass for C9H14BrN3 243 (79Br), 245 (81Br). 6-bromo-2,2,3-trimethyl-2,3-dihydro-1H-imidazo[4,5-b]pyridine: MS (ESI pos. ion) m/z: 242 (MH+, 79Br), 244 (MH+, 81Br). Calculated exact mass for C9H12BrN3 241 (79Br), 243 (81Br).

The synthetic route of 89415-54-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; WO2009/17822; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem