Hydrochloric Acid → HCID 67329355, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution at −5° C. containing 120 mg (0.25 mmol) of 5-bromo-4-methoxy-6-(10-(methoxymethoxy)decyl)-N,N-dimethylpyrimidin-2-amine in 3 mL of anhydrous THF were added 390 μL (0.62 mmol) of 1.6 M solution of n-BuLi in hexanes. The reaction mixture was stirred at −5° C. for 20 min. Then to the mixture were added 84 μL (0.75 mmol) of trimethoxy boron and the reaction mixture was stirred for 1 h. Then to reaction mixture were added 0.55 mL of 30% aq. H2O2 followed by 0.18 mL of 3N aq. NaOH. The reaction mixture was stirred for 30 min and poured into 50-mL of water. The mixture was neutralized with diluted aq. HCl and extracted with two 50-mL portions of ethyl acetate. The combined organic solution was washed with a 80-mL portion of brine, dried (MgSO4) and concentrated under diminished pressure. The residue was purified by chromatography on a silica gel column (10×3 cm). Elution with 2:1 hexanes-ethyl acetate afforded the expected product as colorless oil: yield 47 mg (51%); silica gel TLC Rf 0.50 (2:1 hexanes-ethyl acetate); 1H NMR (CDCl3) δ 1.29-1.21 (br m, 10H), 1.64-1.54 (m, 4H), 2.58 (br s, 2H), 3.07 (s, 6H), 3.33 (s, 3H), 3.48 (t, 2H, J=6.8 Hz), 3.92 (s, 3H) and 4.59 (s, 2H); 13C NMR (CDCl3) δ 26.14, 27.65, 29.29, 29.37, 29.42, 29.45, 29.52, 29.69, 31.19, 37.21, 37.21, 53.24, 55.03, 67.86, 96.32, 126.92, 154.98, 155.94 and 158.04; mass spectrum (APCI+), m/z 370.2700 (M+H) (C19H36N3O3 requires 370.2706).

Provenance & Evidence