Hydrochloric Acid → HCID 53373399, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution at −5° C. containing 500 mg (1.34 mmol) of 5-bromo-4-decyl-6-methoxy-N,N-dimethylpyrimidin-2-amine in 10 mL of anhydrous THF were added 202 μL (1.34 mmol) of N,N,N,N-tretamethyl ethylenediamine followed by 2.09 mL (3.35 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 440 μL (4.02 mmol) of trimethoxy boron and the reaction mixture was stirred at 23° C. for 1 h. Then to reaction mixture were added 3.46 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 111 mg (27%); mp: 59-60° C.; silica gel TLC Rf=0.60 (4:1 hexanes-ethyl acetate); 1H-NMR (methanol-d4) δ 0.87 (t, 3H, J=6.4 Hz), 1.33-1.24 (br m, 14H), 1.62 (quint, 2H, J=7.2 Hz), 2.58 (dd, 2H, J=7.6, 7.6 Hz), 3.09 (s, 6H) and 3.91 (s, 3H); 13C NMR (methanol-d4) δ 13.05, 22.32, 27.62, 29.05, 29.15, 29.17, 29.29, 29.31, 30.58, 31.67, 36.32, 36.32, 52.23, 126.96, 155.92, 155.94 and 159.48.

Provenance & Evidence