4-Aminopyrimidine → HCID 86687725, compound

Participants

Reaction Steps

A vial was charged with perfluorophenyl 1-(5-chloro-2-methoxyphenyl)-4-oxo-3,4-dihydrophthalazine-6-sulfonate (From Step 6, Example 501; 126 mg, 0.236 mmol), pyrimidin-4-amine (33.7 mg, 0.355 mmol), and THF (1.18 mL). The resulting solution was cooled in an ice-water bath for 10 min, then lithium bis(trimethylsilyl)amide (1M in THF) (591 μl, 0.591 mmol) was added drop wise. LCMS after 2 h showed complete conversion of SM to product. The reaction was quenched with 1 mL of MeOH. Purification was done via RPLC with 0.1% NH4OH in ACN and water as mobile phase to afford 1-(5-chloro-2-methoxyphenyl)-4-oxo-N-(pyrimidin-4-yl)-3,4-dihydrophthalazine-6-sulfonamide (27 mg, 25.7% yield). m/z (ESI) 444.0 (M+H)+.

Provenance & Evidence