Acetic Anhydride → HCID 58504508, compound

Participants

Reaction Conditions

Reaction Steps

In a 25 mL sealable tube under argon were combined 4-[2-amino-6-(1-piperidinyl)-4-pyrimidinyl]-2-fluorobenzonitrile (0.18 g, 0.44 mmol) and acetic anhydride (5 mL). The vial was sealed and the reaction mixture was stirred at 95° C. After 16 hours, LCMS indicated a mixture of 2:1 bis:mono acetylated products. The reaction mixture was cooled to room temperature and concentrated. To the resulting crude mixture (192 mg) was added CH3OH (10 mL) followed by DMAP (0.046 g, 0.38 mmol) and the reaction mixture was stirred overnight at 30° C. Additional DMAP (30 mg) was added and the reaction mixture was stirred for an additional 24 hours. The reaction was concentrated, and the resulting oil was partitioned between EtOAc and water. The organic layer was separated, dried (MgSO4), filtered and concentrated to afford the title compound (150 mg, some DMAP is present) as a light yellow solid. LC-MS (ES) m/z=340 [M+H]+.

Provenance & Evidence