1-Bromononane → HCID 67356396, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution at −78° C. containing 1.00 g (3.25 mmol) of 5-(Benzyloxy)-2-(2,5-dimethyl-1H-pyrrol-1-yl)-4,6-dimethylpyrimidine and 415 mg (2.16 mmol) of 1-bromononane in 30 mL of anhydrous THF were added 2.70 mL (4.32 mmol) of a 1.60 M solution of n-BuLi in pentane. The reaction mixture was stirred at 23° C. for 30 min. The reaction was quenched with saturated aqueous ammonium chloride and then poured into 70 mL of water. The mixture was then extracted with two 70-mL portions of diethyl ether. The combined organic layer was then washed with a 100-mL portion of brine, dried (MgSO4) and then concentrated under diminished pressure. The residue was purified by chromatography on a silica gel column (15×5 cm). Elution with 4:1 hexanes-diethyl ether afforded the expected product as light colorless oil: yield 502 mg (53%); silica gel TLC Rf 0.60 (4:1 hexanes-diethyl ether); 1H NMR (CDCl3) δ0.89 (t, 3H, J=7.2 Hz), 1.20-1.30 (m, 14H), 1.75 (m, 2H), 2.31 (s, 6H), 2.48 (s, 3H), 2.77 (dd, 2H, J=7.6, 7.6 Hz), 4.90 (s, 2H), 5.86 (s, 2H) and 7.40-7.44 (m, 5H); 13C NMR (CDCl3) δ 14.10, 14.33, 19.28, 22.67 27.74, 29.29, 29.29, 29.41, 29.51, 29.57, 31.62, 31.88, 75.72, 107.91, 128.01, 128.22, 128.72, 129.30, 129.30, 136.22, 147.35, 147.35, 152.59, 161.59 and 165.09; mass spectrum (APCI), m/z 434.3172 (M+H)+ (C28H40N30 requires 434.3171).

Provenance & Evidence