Sodium Carbonate → 2-(2'-Fluoro-4'-octyloxyphenyl)-5-bromopyrimidine

Participants

Reaction Steps

--Quantities: 5-bromo-2-iodopyrimidine 2 (4.05 g, 14.2 mmol), 2-fluoro-4-octyloxyphenylboronic acid 5 (4.57 g, 17.0 mmol), tetrakis(triphenylphosphine)palladium (328 mg, 0.28 mmol), 2M sodium carbonate (50 ml), DME (50 ml). The experimental procedure was as described for compound 4 to yield the monofluorophenylpyrimidine 6 (3.68 g, 69%) (from MeOH), m.p. 71.6° C.; νmax /cm-1 (KBr) 2920, 2850, 1610, 1410, 1270, 1125 and 830; δ 0.90 (3H, t, Me), 1.20-1.55 (10H, m), 1.82 (2H, quint, OCH2CH2), 4.00 (2H, t, OCH2), 6.75 (2H, m, 3'- and 4'-H), 8.06 (1H, t, 6'-H) and 8.85 (2H, s, 4- and 6-H); m/z 382 (M+), 380 (M+), 270 (M+ -C8H16), 268 (M+ -C8H16) and 137.

Provenance & Evidence