Ethyl 1-propenyl ether → 2-Chloro-5-(2-ethoxy-vinyl)-pyrimidin-4-ylamine

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Reaction Steps

5-Bromo-2-chloro-pyrimidin-4-ylamine (88.0 g, 0.43 mol), 1-ethoxy-propene (220 g, 0.49 mol), Pd(PPh3)2Cl2 (35.0 g, 0.05 mol) and Et4NCl (67.0 g, 0.40 mol) are suspended in solvent (750 mL, DME/toluene/H2O/EtOH 10:1:3:6) under nitrogen. The reaction mixture is heated to reflux for 24 h, cooled to rt, and then diluted with water. The aqueous layer is extracted with EtOAc (3×). The combined organic layers are dried over MgSO4, filtered, and concentrated under reduced pressure. The residue is purified by column chromatography (SiO2, gradient elution, EtOAc/petroleumether 1:10>1:4) to yield the title compound as a yellow solid.

Provenance & Evidence