Methyl 2-azidoacetate → HCID 118103403, compound

Participants

Reaction Steps

A mixture of methyl azidoacetate (160 mg, 0.452 mmol), sodium 2-(1,2-dihydroxyethyl)-4-hydroxy-5-oxo-2,5-dihydrofuran-3-olate (130 mg, 0.656 mmol), copper sulfate (0.100 mL, 0.100 mmol) in ethanol (2.00 mL) and water (0.500 mL) was added to a solution of N-[3-(6-ethynylpyridin-3-yl)-5-methylphenyl]-4-(trifluoromethyl)pyrimidin-2-amine (100 mg, 0.869 mmol) in DMF (0.500 mL). The mixture was stirred at room temperature for 1 hour. The mixture was diluted with water and extracted with ethyl acetate. The organic layer was concentrated under reduced pressure and the residue was purified by silica gel chromatography (50% ethyl acetate in hexanes) to afford methyl {4-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)pyridin-2-yl]-1H-1,2,3-triazol-1-yl}acetate. MS APCI C22H19F3N7O2 [M+H]+ 470. found 470. 1H NMR (500 MHz, DMSO-d6) δ 10.29 (s, 1H), 8.89-8.86 (m, 1H), 8.84 (d, J=5.1 Hz, 1H), 8.66 (s, 2H), 8.05-7.98 (m, 1H), 7.58 (s, 1H), 7.28 (d, J=5.1 Hz, 1H), 7.26 (s, 1H), 5.50 (s, 2H), 3.72 (d, J=14.9 Hz, 3H), 2.37 (s, 3H).

Provenance & Evidence