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0 °C

To a solution of 5-(3-fluoropyridin-4-yl)-6-pyridin-3-ylpyrazin-2-amine (Example 115) (150 mg, 0.56 mmol) in CH2Cl2 (5 mL) was added pyridine (1 mL), cooled at 0° C., propionyl chloride (57 mg, 0.62 mmol) was added dropwise. Upon complete addition, the ice bath was removed and the reaction continued at room temperature overnight. Then CH2Cl2 (10 mL) and aqueous NaOH 10% (10 mL) were added, the organic layer was separated, and washed with H2O and saturated NaCl. The combined organic layers were dried over Na2SO4, filtered and concentrated in vaccuo. The crude product was purified by column chromatography on silica gel, eluting with an EtOAc/hexane gradient (80-100%), yielding the target product (100 mg, 55%)

1. additionUpon complete addition
2. customthe ice bath was removed
3. additionThen CH2Cl2 (10 mL) and aqueous NaOH 10% (10 mL) were added
4. customthe organic layer was separated
5. washwashed with H2O and saturated NaCl
6. dry with materialThe combined organic layers were dried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated in vaccuo
9. customThe crude product was purified by column chromatography on silica gel
10. washeluting with an EtOAc/hexane gradient (80-100%)