Sodium Bicarbonate → HCID 58777633, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of [4-amino-2-(1-methanesulfonyl-piperidin-4-ylamino)-pyrimidin-5-yl]-(2,3-difluoro-6-methoxy-phenyl)-methanone (200 mg, 0.45 mmol, Example 105) in methylene chloride (40 mL) was treated at 0-5° C. with aluminum chloride (620 mg, 4.7 mmol). The solution was stirred at ˜7° C. for 2.5 hours and treated with ice water (20 mL). The mixture was treated with 10% NaHCO3 (15 mL) and extracted with a mixture of tetrahydrofuran and methylene chloride (2×), dried (Na2SO4), and filtered. Removal of solvent gave an oil that crystallized upon trituration with methylene chloride. This crude solid was purified by silica gel chromatography (5-10% methanol/methylene chloride to give [4-amino-2-(1-methanesulfonyl-piperidin-4-ylamino)-pyrimidin-5-yl]-(2,3-difluoro-6-hydroxy-phenyl)-methanone as a white solid (75 mg, 39%) after solvent removal. HRMS, observed: 428.1203; Calcd for (M+H)+: 428.1199

Provenance & Evidence