Diisopropylamine → 2-(2',3'-Difluoro-4'-octyloxyphenyl)-5-non-1-ynylpyrimidine

Participants

Reaction Steps

-Non-1-yne (1.0 ml, 6.4 mmol) was added via syringe to degassed mixture of 2-(2',3'-difluoro-4'-octyloxyphenyl)-5-bromopyrimidine 4 (1.27 g, 3.18 mmol), tetrakis(triphenylphosphine)palladium (173 mg, 0.15 mmol) and copper(I) iodide (29 mg, 0.15 mmol) in diisopropylamine (60 ml) under nitrogen. The mixture was heated under gentle reflux for 4 h. The solvent was removed in vacuo and the residue was purified by flash chromatography (5% ethyl acetate-light petroleum, the sample was preloaded onto silica in dichloromethane) to give the nonynylpyrimidine 38 (1.29 g, 92%) (from MeOH), transitions/° C. K 64.4 (N 63.3) I; νmax /cm-1 (KBr) 2920, 2850, 2220, 1615, 1520, 1470, 1430s, 1295, 1205 and 1090s; δ 0.90 (6 H, m), 1.20-1.55 (18 H, m), 1.64 (2 H, quint, J 7, CH2CH2C≡C), 1.85 (2 H, quint, J 7, OCH2CH2), 2.46 (2 H, t, J 7, CH2C≡C), 4.10 (2 H, t, J 7, OCH2), 6.83 (1H, ddd, J 8, 7 and 2, 5'-H), 7.85 (1H, ddd, J 8, 7 and 2, 6'-H_ an d8.79 (2 H, s, 4- and 6-H), m/z 442 (M+), 330, 288, 287, 274, 273, 247 and 220.

Provenance & Evidence