Triethylamine → (R,E)-ethyl 3-(2-amino-4-methyl-6-(tetrahydrofuran-3-ylamino)pyrimidin-5-yl)acrylate

Participants

Reaction Conditions

Reaction Steps

To a solution of (R)-5-iodo-6-methyl-N4-(tetrahydrofuran-3-yl)pyrimidine-2,4-diamine (4.53 g, 14.2 mmol), ethyl acrylate (4.25 g, 42.5 mmol) and triethylamine (4.30 g, 42.5 mmol) in DMF (150 mL) was added Pd(PPh3)4 (1.635 g, 10 mol %) under nitrogen at room temperature. The resulting mixture was heated to 95° C. for 18 h under a nitrogen atmosphere. After the reaction was complete by LC/MS, the resulting mixture was concentrated under reduced pressure and directly subjected to column chromatography purification to give (R,E)-ethyl 3-(2-amino-4-methyl-6-(tetrahydrofuran-3-ylamino)pyrimidin-5-yl)acrylate (3.90 g, 94% yield). MS (EI) for C14H20N4O: 293.2 (MH+).

Provenance & Evidence