Sodium Thiosulfate → HCID 178517773, compound

Participants

Reaction Steps

To 8-cyclopropyl-2-(difluoro(5-fluoropyridin-2-yl)methyl)-4-(methylthio)quinazoline (150 mg, 0.41 mmol) in DCM (5 mL) cooled to 0° C. was added 3-chloroperbenzoic acid (70%, 42 mg, 0.17 mmol) and the mixture stirred for 15 min. The mixture was diluted with DCM and then a sodium thiosulfate solution, followed by a saturated sodium bicarbonate solution was added. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. To the obtained residue was added THF (4 mL) and 5-methyl-1H-pyrazol-3-amine (185 mg, 1.9 mmol) and the mixture stirred at rt for 30 min. The crude mixture was concentrated under reduced pressure and then purified by preparative HPLC (Varian C-18 reverse phase column, eluted with gradient of solvent B=0.05% formic acid/ACN and solvent A=5% ACN/0.05% formic acid/H2O) to afford 8-cyclopropyl-2-(difluoro(5-fluoropyridin-2-yl)methyl)quinazolin-4-ol (50 mg, 37%). LC-MS (ESI) m/z 332 (M+H)+.

Provenance & Evidence