Dimethyl Sulfoxide → HCID 178504689, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 8-bromo-2-(difluoro(5-fluoropyridin-2-yl)methyl)-4-(methylthio)quinazoline from Example 35 step B (400 mg, 1 mmol), copper(I) trifluoromethanesulfonate benzene complex (503 mg, 1 mmol), sodium methanesulfinate (752 mg, 6.26 mmol) and N,N-dimethylethylenediamine (0.039 mL, 0.36 mmol) was added DMSO (15 mL). The reaction vessel was evacuated and flushed with argon (2×), and the mixture was heated in a microwave synthesizer at 120° C. for 10 min. The mixture was filtered and the filtrate was purified by preparative HPLC (Varian diphenyl reverse phase column, eluted with gradient of solvent B=0.05% AcOH/ACN and solvent A=5% ACN/0.05% AcOH/H2O) to afford 2-(difluoro(5-fluoropyridin-2-yl)methyl)-8-(methylsulfonyl)quinazolin-4-ol (100 mg, 27%). 1H NMR (300 MHz, DMSO-d6) δ ppm 3.22 (s, 3H) 7.81 (t, J=7.82 Hz, 1H) 8.00-8.11 (m, 2H) 8.38 (dd, J=7.54, 1.32 Hz, 1H) 8.45-8.51 (m, 1H) 8.71 (d, J=2.07 Hz, 1H) 13.64-13.78 (m, 1H).

Provenance & Evidence