Lithium Hydroxide → HCID 73603938, compound

Participants

Reaction Conditions

Reaction Steps

N-[(4aR,7aR)-6-[5-fluoro-4-(1-hydroxy-1-methyl-ethyl)pyrimidin-2-yl]-7a-pyrazin-2-yl-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazin-2-yl]benzamide (330 mg, 0.668 mmol) is dissolved in methanol (8 mL) with stirring. Lithium hydroxide (42.51 mg, 1 mmol) is added and the reaction is heated at 60° C. for 5 hours 30 minutes. The reaction is cooled to room temperature and loaded onto a silica gel column. The column is eluted with a 0-5% gradient of 0.14 M ammonia/methanol in dichloromethane. The product obtained is further purified by preparative HPLC using a 10% B to 100% B gradient over 9 minutes at 60 mL/minute (column=Phenomenex Gemini NX C18, 30×100 mm, 5 μm. Mobile phase A: water with 10 mM ammonium bicarbonate, pH adjusted to pH 10 with ammonia. Mobile phase B: acetonitrile) to give the title compound (146 mg, 56%). ES/MS (m/e): 390 (M+1).

Provenance & Evidence