Dichloromethane → HCID 86698565, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution containing 240 mg (0.58 mmol) of 5-(benzyloxy)-4-(10-(methoxymethoxy)decyl)-6-methylpyrimidin-2-amine in 10 mL of anhydrous DCM were added 1.10 g (5.80 mmol) of benzyltrimethylammonium chloride followed by 696 μL (5.80 mmol) of t-butyl nitrite. The reaction mixture was stirred at 23° C. protected from light for 15 h. The mixture was filtered and the filtrate was concentrated under diminished pressure. The residue was purified by chromatography on a silica gel column (3×10 cm). Elution with 4:1 hexanes-ethyl acetate afforded the expected product as a colorless oil: yield 44 mg (16%); silica gel TLC Rf 0.45 (4:1 hexanes-ethyl acetate); 1H NMR (CDCl3) δ 1.24 (br s, 12H), 1.55 (quint, 2H, J=7.2 Hz), 1.65 (quint, 2H, J=6.8 Hz), 2.42 (s, 3H), 2.67 (dd, 2H, J=8.0, 8.0 Hz), 3.33 (s, 3H), 3.47 (t, 2H, J=6.8 Hz), 4.59 (s, 2H), 4.83 (s, 2H) and 7.37 (m, 5H); 13C NMR (CDCl3) δ 19.32, 26.16, 28.14, 29.25, 29.35, 29.35, 29.47, 29.51, 29.71, 31.92, 55.04, 67.85, 76.03, 96.36, 128.08, 128.73, 128.73, 128.77, 128.77, 135.73, 149.01, 154.24, 163.79 and 167.41; mass spectrum (APCI), m/z (M+H)+435.2411 (C24H36N2O3Cl requires 435.2415)

Provenance & Evidence