Hydrogen Peroxide → 2-(2',3'-Difluoro-4'-octyloxyphenyl)-5-hydroxypyrimidine

Participants

Reaction Steps

--Quantities: difluorophenylbromo-pyrimidine 4 (4.30 g, 10.8 mmol), 2.5M butyllithium (4.5 ml, 11.3 mmol), trimethyl borate (2.6 ml, 22.6 mmol), THF (100 ml), hexane (30 ml), 30% hydrogen peroxide (5.4 ml, 44 mmol) ether (200 ml). The experimental procedure was as described for compound 33. The crude product was purified by flash chromatography (10 to 30% ethyl acetate-light petroleum) to give the difluorophenyl-5-hydroxypyrimidine 35 (2.04 g, 56%) [from light petroleum (b.p. 60-80° C.)], m.p. 84-85° C.; νmax /cm-1 (KBr) 3 100br, 2920, 2850, 1620, 1560, 1510, 1475, 1430, 1300, 1285, 1200 and 1085; δ 0.91 (3H, t, Me), 1.19-1.52 (10H, m), 1.32 (2H, quint, OCH2CH2), 4.05(2H, t, OCH2), 6.79 (1H, ddd, J8, 7 and 2, 5'-H), 7.59 (1H, ddd, J8.5, 7 and 2, 6'-H) and 8.38 (2 H, s, 4- and 6-H); m/z 336 (M+), 335, 237, 223, 208, 195 and 155.

Provenance & Evidence