Ethanol → HCID 86628368, compound

Participants

Reaction Steps

3-{4-Amino-6-chloro-2-[(E)-2-phenylethenyl]-5-pyrimidinyl}propanamide (0.175 g, 0.58 mmol) was dissolved in EtOH and HCl gas was bubbled through the solution until saturated. The solution was heated at reflux for 2 h, cooled to ambient temperature and concentrated under vacuum. The residue was dissolved in water, neutralised to pH9 with K2CO3 solution and extracted with EtOAc (3×). The organic layers were combined, dried over Na2SO4, filtered and concentrated under vacuum to yield ethyl 3-{4-amino-6-chloro-2-[(E)-2-phenylethenyl]-5-pyrimidinyl}propanoate as a white solid. LCMS: m/z 332.2 (MH+). This product was then dissolved in DMF (5 mL), treated with K2CO3 (0.16 g, 1.16 mmol) and heated at 75° C. for 30 minutes. The solution was cooled, diluted with water and extracted with Et2O (3×). The organic layer was dried over Na2SO4, filtered, and concentrated under vacuum. The crude residue was then purified by column chromatography (silica gel) with DCM/(DCM:MeOH:NH4OH) 90:10:1 to yield an additional 0.11 g of the desired compound.

Provenance & Evidence