2-Amino-4-methylthiazole → 3-[6-[(4-Methyl-1,3-thiazol-2-yl)amino]-2-pyridinyl]-1,3-oxazinan-2-one

Participants

Reaction Conditions

Reaction Steps

**_September 21 2015_** 4-methylthiazol-2-amine (85 mg, 0.74 mmol), 3-(6-bromopyridin-2-yl)-1,3-oxazinan-2-one (191 mg, 0.74 mmol), 3-(6-bromopyridin-2-yl)-1,3-oxazinan-2-one (191 mg, 0.74 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (43.1 mg, 0.07 mmol) and cesium carbonate (291 mg, 0.89 mmol) in toluene (5 mL) were microwaved at 120 °C under N2 for one hour. LCMS showed no precursors and 51% of the desired mass MH+291 @ 0.86 min on a 2-min basic run. The reaction mixture was diluted with EtOAc, washed with water, filtered, and evaporated to give a brown solid as the crude product. The crude product was added to a Biotage column, and was eluted with 15-100%EtOAc in Heptane. Collected fractions. **_September 22 2015_** Based on TLC and LCMS, the product fractions were combined, and evpoarated to give an yellow-brown solid (94 mg). Based on LCMS, it was only 89% pure. Based on LCMS, it was 96% pure; based on NMR, it was > 95% pure.

Provenance & Evidence