Sodium Carbonate → HCID 136344412, compound

Participants

Reaction Conditions

Reaction Steps

A microwave reaction vial was charged with 2-chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-3H-pyrrolo[2,3-d]pyrimidin-4(7H)-one (53.7 mg, 179 mop and ethanol (850 μL) (650 μL+200 μL rinse). The resulting mixture was treated with a 2M aqueous sodium carbonate solution (270 μL, 540 μmol), 4-(trifluoromethyl)phenylboronic acid (42.1 mg, 222 μmol), and tetrakis(triphenylphosphine)palladium(0) (13.2 mg, 11.4 μmol). The vial was tightly sealed and heated in a microwave at 150° C. for 8 min. At this time, the reaction was filtered through a pad of Celite®, rinsing copiously with methanol, and the filtrate was concentrated in vacuo onto Celite®. Flash chromatography (12 g silica gel column, 10-40% ethyl acetate/hexanes) afforded 2-(4-(trifluoromethyl)phenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-3H-pyrrolo[2,3-d]pyrimidin-4(7H)-one as a light yellow solid (47.7 mg, 65.0%). 1H NMR (300 MHz, DMSO-d6) δ ppm −0.13 (s, 9H) 0.85 (t, J=8.10 Hz, 2H) 3.56 (t, J=8.10 Hz, 2H) 5.58 (s, 2H) 6.59 (d, J=3.39 Hz, 1H) 7.34 (d, J=3.39 Hz, 1H) 7.90 (d, J=7.91 Hz, 2H) 8.36 (d, J=8.29 Hz, 2H) 12.45 (s, 1H). LC-MS calcd. for C19H23F3N3O2Si [(M+H)4] 410, obsd. 410.1.

Provenance & Evidence