4-(Trifluoromethoxy)phenylboronic acid → 5-(Ethoxymethoxy)-2-[4-(trifluoromethoxy)phenyl]pyrimidine

Participants

Reaction Steps

Suzuki coupling of chloropyrimidine 108 (see Example 2S) and 4-(trifluoromethoxy)phenylboronic acid as in Example 2S above for 2 h, followed by chromatography of the product on silica gel, eluting with 0-2% Et2O/petroleum ether (foreruns) and then with 2% Et2O/petroleum ether, gave 5-(ethoxymethoxy)-2-[4-(trifluoromethoxy)phenyl]pyrimidine (110) (91%) as a white solid: mp (petroleum ether) 41-43° C.; 1H NMR (CDCl3) δ 8.60 (s, 2H), 8.41 (dt, J=9.0, 2.4 Hz, 2H), 7.30 (br dd, J=9.0, 0.9 Hz, 2H), 5.31 (s, 2H), 3.77 (q, J=7.1 Hz, 2H), 1.25 (t, J=7.1 Hz, 3H); HRESIMS calcd for C14H14F3N2O3 m/z [M+H]+ 315.0951. found 315.0944.

Provenance & Evidence