Hydrochloric Acid → HCID 53373129, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution at −5° C. containing 500 mg (1.10 mmol) of 5-bromo-4-hexadecyl-6-methoxy-N,N-dimethylpyrimidin-2-amine in 10 mL of anhydrous THF were added 166 μL (1.10 mmol) of N,N,N,N-tretamethyl ethylenediamine followed by 1.72 mL (2.75 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 369 μL (3.30 mmol) of trimethoxy boron and the reaction mixture was stirred at 23° C. for 1 h. Then to reaction mixture were added 2.84 mL of 30% aq. H2O2 The reaction mixture was then stirred for 30 min and poured into 100 mL of water. The mixture was neutralized with diluted aq. HCl and extracted with two 100-mL portions of ethyl acetate. The combined organic solution was washed with a 100-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 4:1 hexanes-ethyl acetate afforded the expected product as white solid: yield 240 mg (55%); mp: 78-79° C.; silica gel TLC Rf=0.50 (4:1 hexanes-ethyl acetate); 1H-NMR (dmso-d6) δ 0.81 (t, 3H, J=6.0 Hz), 1.23-1.19 (br m, 26H), 1.52 (quint, 2H, J=6.8 Hz), 2.46 (dd, 2H, J=7.2, 7.2 Hz), 2.97 (s, 6H) and 3.82 (s, 3H); 13C NMR (dmso-d6) δ 14.38, 22.53, 27.65, 29.14, 29.27, 29.32, 29.38, 29.43, 29.46, 29.46, 29.46, 29.46, 29.46, 29.46, 31.20, 31.73, 37.27, 37.27, 53.13, 127.10, 155.54, 156.81 and 159.70.

Provenance & Evidence