5-Iodo-3-methyl-2-pyridinamine

To dioxane (10 mL) was added 5-bromo-3-methylpyridin-2-amine (2 g, 10.6 mmol), sodium iodide (3.2 g, 21.4 mmoL), copper iodide (0.190 g, 1.06 mmol) and the solution degassed followed by addition of tetramethylethane-1, 2-diamine (0.803 mL, 1.06 mmol) this mixture heated at 110° C. overnight. After cooling water was added and extracted the crude product with ethyl acetate. The residue was purified by column chromatography to give 5-iodo-3-methylpyridin-2-amine as a beige solid (2.3 g, 93percent). Analogous to the procedure described in Ex. 40, 6-fluoro-7-(methylamino)-2, 3-dihydrobenzo[e][1, 3]oxazin-4-one (0.100 g, 0.51 mmol) and 5-iodo-3-methylpyridin-2-amine (0.119 g, 0.53 mmol) were coupled to yield pure 3-(6-aminopyridin-3-yl)-6-fluoro-7-(methylamino)-2, 3-dihydrobenzo[e][1, 3]oxazin-4-one (0.020 g, 13percent) after reverse phase HPLC purification. ES-MS (M+H)In a 250-mL round-bottomed flask, a solution of 3-methylpyridin-2-amine (4.57 g, 42.3 mmol) in AcOH (50 mL) was cooled to 0 °C. NIS (9.5 g, 42 mmol, Sigma- Aldrich, India) was added in portions to the above solution at the same temperature under nitrogen atmosphere. The reaction mixture was warmed to room temperature and stirred at room temperature for 3 h. The reaction mixture was diluted with cold water (100 mL), followed by a mixture of 5percent NaTo a cooled (0 C.) solution of ethyl (1E)-N-(2, 4, 6-trimethylphenyl)sulfonyloxyethanimidate (0.732 g, 2.56 mmol) in dioxane (3.2 mL) was added 70% perchloric acid (2.75 mL, 32.2 mmol) dropwise. Following the addition, the temperature was maintained at 0 C. for 10 minutes and then ice-cold water (13 mL) was added at once. The resulting precipitate was collected by vacuum filtration and washed with water (caution: this compound has been reported to be potentially explosive when dry). The white solid was immediately dissolved in DCM (5.5 mL), dried over Na2SO4, and filtered. The filtrate was then added dropwise to a cooled (0 C.) solution of

Molecular Weight:234.04
XLogP3:1.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:233.96540
Monoisotopic Mass:233.96540
Topological Polar Surface Area:38.9
Heavy Atom Count:9
Complexity:97.1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes