HCID 67329637, compound → HCID 67329285, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution containing 933 mg (5.58 mmol) of 4-methoxy-N,N,6-trimethylpyrimidin-2-amine and 1.5 g (5.58 mmol) of 1-Bromo-9-(methoxymethoxy)nonane in 20 mL of anhydrous THF were added 5.23 mL (8.37 mmol) of 1.6 M n-BuLi in hexanes. The reaction mixture was stirred at 23° C. for 20 min. The reaction mixture was quenched with saturated aqueous ammonium chloride and poured into 100 mL of water. The compound was extracted with two 80-mL portions of ethyl acetate. The combined organic layer was washed with one 80-mL portion of brine, dried (MgSO4) and concentrated under diminished pressure. The residue was purified by chromatography on a silica gel column (15×5 cm). Elution with 9:1 hexanes-ethyl acetate afforded the expected product as colorless oil: yield 1.41 g (71%); silica gel TLC Rf 0.45 (9:1 hexanes-ethyl acetate); 1H-NMR (CDCl3) δ 1.24-1.32 (br m, 10H), 1.82 (m, 4H), 2.48 (dd, 2H, J=8.0, 8.0 Hz), 3.14 (s, 6H), 3.33 (s, 3H), 3.48 (t, 2H, J=6.8 Hz), 3.85 (s, 3H), 4.59 (s, 2H) and 5.76 (s, 1H); 13C NMR (CDCl3) δ 26.18, 28.46, 28.66, 29.29, 29.39, 29.45, 29.54, 29.72, 36.77, 37.81, 37.81, 52.74, 55.04, 67.85, 93.03, 96.35, 162.35, 170.25 and 172.03; mass spectrum (APCI+), m/z 354.2766 (M+H) (C19H36N3O3 requires 254.2757).

Provenance & Evidence