[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[C:8]([C:12]1[CH:21]=[CH:20][C:15]([C:16](=O)[CH2:17]Cl)=[CH:14][CH:13]=1)([CH3:11])([CH3:10])[CH3:9].C(=O)(O)[O-].[Na+]>C(O)(C)C>[C:8]([C:12]1[CH:13]=[CH:14][C:15]([C:16]2[N:1]=[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][N:3]3[CH:17]=2)=[CH:20][CH:21]=1)([CH3:11])([CH3:10])[CH3:9]A solution of 2-aminopyridine (0.512 g, 5.44 mmol) and 4-tert-butylphenacyl chloride (1.26 g, 5.98 mmol) in isopropanol (16 mL) was treated with sodium bicarbonate (0.914 g, 10.9 mmol) and heated in a sealed tube at 80° C. overnight. The mixture was concentrated under reduced pressure, re-dissolved in ethyl acetate (200 mL) and washed with water (2×100 mL) and saturated sodium chloride (100 mL). The organic layer was dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude material was purified by flash silica gel chromatography, eluting with 20% acetone/hexanes to yield 0.841 g (62%) of the purified product. MS (ESI) m/z 251.1528; HPLC (Method B): r.t.=8.4 min., purity 100% at 210-370 nm, 100% at 306 nm. HRMS: calcd for C17H18N2+H+, 251.15427; found (ESI, [M+H]+), 251.1528.
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