Diisopropylethylamine → Tert-butyl 4-(4-(1-(4-hydroxyphenyl)cyclopropylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzoate

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl 4-(4-chloro-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzoate (2 g, 4.94 mmol) in THF (30 mL) was added 4-(1-aminocyclopropyl)phenol (0.811 g, 5.44 mmol) and Hunig's Base (3.45 mL, 19.76 mmol). The resulting mixture was stirred for 16 h. The reaction was then warmed to 65° C. for 2 h at which point the reaction became a homogeneous solution. The reaction was cooled and diluted with DCM and washed with water and brine. The organic layer was collected, dried over sodium sulfate, and concentrated under vacuum to give an oily residue. The residue was purified by silica gel chromatography using 20-40% EtOAc/Hexanes to give tert-butyl 4-(4-(1-(4-hydroxyphenyl)cyclopropylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzoate (2 g). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.30-1.37 (m, 4H), 1.60 (s, 9H), 4.67-4.77 (m, 2H), 4.85 (br. s., 1H), 6.04 (br. s., 1H), 6.70-6.81 (m, 2H), 7.11-7.22 (m, 2H), 7.47-7.66 (m, 2H), 7.79-8.01 (m, 2H); LC-MS (Condition A), MS m/z (M++H) 518.0.

Provenance & Evidence