Sodium Carbonate → HCID 136247182, compound

Participants

Reaction Conditions

Reaction Steps

A microwave reaction vial was charged with 7-but-3-enyl-2-chloro-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-4-one (Intermediate B) (96.1 mg, 430 μmol,), ethanol (1.6 mL), a 2M aqueous sodium carbonate solution (645 μL, 1.29 mmol), 4-(trifluoromethyl)phenylboronic acid (98.2 mg, 517 μmol), and tetrakis(triphenylphosphine)palladium(0) (27.2 mg, 23.5 μmol). The reaction was heated in a microwave at 150° C. for 68 min. The reaction was filtered through a pad of Celite®, rinsing with ethanol. The filtrate was concentrated in vacuo onto Celite®. Flash chromatography (12 g silica gel column, 10-30% ethyl acetate/hexanes) afforded 7-but-3-enyl-2-(4-trifluoromethyl-phenyl)-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-4-one (98.9 mg, 69.1%) as an off-white solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 2.59 (q, J=6.66 Hz, 2H) 4.29 (t, J=6.88 Hz, 2H) 4.84-5.21 (m, 2H) 5.58-5.95 (m, 1H) 6.52 (d, J=3.20 Hz, 1H) 7.25 (d, J=3.20 Hz, 1H) 7.90 (d, J=8.29 Hz, 2H) 8.34 (d, J=7.91 Hz, 2H) 12.32 (s, 1H). LC-MS calcd. for C17H15F3N3O [(M+H)+] 334, obsd. 334.1.

Provenance & Evidence