Methanol → HCID 67329649, compound

Participants

Reaction Steps

To a stirred solution containing 41.0 mg (0.09 mmol) of 5-(benzyloxy)-2-chloro-4-(10-(methoxymethoxy)decyl)-6-methylpyrimidine in 5 mL of anhydrous methanol were added 22 mg (0.94 mmol) of sodium. The mixture was then stirred at reflux for 16 h. The reaction was quenched with water and poured into 50 mL of water. The mixture was extracted with two 50-mL portions of ethyl acetate. The combined organic solution was washed with one 50-mL portion of brine, dried (MgSO4) and concentrated under diminished pressure. The residue was purified by chromatography on a silica gel column (2×6 cm). Elution with 1:1 hexanes-ethyl acetate afforded the expected product as a colorless oil: yield 30 mg (74%); silica gel TLC Rf 0.65 (1:1 hexanes-ethyl acetate); 1H NMR (CDCl3) δ 1.24 (br m, 12H), 1.55 (quint, 2H, J=6.8 Hz), 1.68 (quint, 2H, J=7.6 Hz), 2.37 (s, 3H), 2.65 (dd, 2H, J=7.6, 7.6 Hz), 3.33 (s, 3H), 3.48 (t, 2H, J=6.8 Hz), 3.93 (s, 3H), 4.59 (s, 2H), 4.83 (s, 2H) and 7.37 (m, 5H); 13C NMR (CDCl3) δ 19.21, 26.16, 27.85, 29.36, 29.40, 29.51, 29.53, 29.71, 31.71, 54.69, 55.02, 67.85, 75.80, 96.36, 127.49, 128.38, 128.38, 128.63, 128.63, 136.50, 145.14, 160.61, 162.38 and 165.87; mass spectrum (APCI), m/z (M+H)+431.2910 (C25H39N2O4 requires 431.2910).

Provenance & Evidence