3-Aminopyridine → 2-(2-(5-Chloro-2-(pyridin-3-ylamino)pyrimidin-4-ylethyl)phenyl)propanamide

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Reaction Conditions

Reaction Steps

A mixture of 2-(2-(2-(5-chloro-2-(1-methyl-1H-pyrazol-4-ylamino)pyrimidin-4-ylethyl)phenyl)propanamide A30 (0.080 g, 0.25 mmol), 3-aminopyridine (0.046 g, 0.49 mmol), Xantphos (0.0057 g, 0.010 mmol) and Cs2CO3 (0.24 g, 0.74 mmol) in 1,4-dioxane (3 mL) was bubbled with nitrogen for 10 minutes. Palladium (II) acetate (0.0011 g, 0.0049 mmol) was added and the mixture was heated at 120° C. under microwave irradiation for 28 minutes. The volatiles were removed in vacuo and the residue was purified by silica gel column chromatography (Combiflash Rf, 0-10% MeOH in DCM) to give the title compound 39 as a pink solid (0.029 g, 31%). LCMS-C: rt 4.30 min; m/z 382 [M+H]+.

Provenance & Evidence