4-Aminopyrimidine → HCID 86687728, compound

Participants

Reaction Steps

A vial was charged with perfluorophenyl 1-(2-methoxy-4-(trifluoromethyl)phenyl)-4-oxo-3,4-dihydrophthalazine-6-sulfonate (From Step 5, Example 293; 126 mg, 0.222 mmol), pyrimidin-4-amine (31.7 mg, 0.334 mmol), and THF (1.11 mL). The resulting solution was cooled in an ice-water bath for 10 min, then lithium bis(trimethylsilyl)amide (1M in THF) (489 μl, 0.489 mmol) was added drop wise. LCMS after 15 min showed complete conversion of SM to product. The reaction was quenched with 1 mL of MeOH and concentrated. Purification was done on OJ-H column, with 20% methanol and 0.2% diethylamine. Since the product contained some DEA, it was purified further by mass directed LC purification with TFA to afford 1-(2-methoxy-4-(trifluoromethyl)phenyl)-4-oxo-N-(pyrimidin-4-yl)-3,4-dihydrophthalazine-6-sulfonamide (23 mg, 21.7% yield). m/z (ESI) 478.0 (M+H)+.

Provenance & Evidence