Dimethyl Sulfoxide → HCID 178504655, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 7-bromo-2-(difluoro(5-fluoropyridin-2-yl)methyl)-4-(methylthio)quinazoline from Example 7 step C (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×). The mixture was then heated in a microwave synthesizer at 130° 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)-7-(methylsulfonyl)quinazolin-4-ol (155 mg, 42%). 1H NMR (300 MHz, DMSO-d6) δ ppm 7.98-8.13 (m, 3H) 8.19 (s, 1H) 8.40 (d, J=8.29 Hz, 1H) 8.68 (d, J=2.45 Hz, 1H) 13.50 (br s, 1H).

Provenance & Evidence