HCID 67329355, compound → HCID 53373128, compound

Participants

Reaction Steps

To a stirred solution containing 20 mg (0.054 mmol) of 2-(dimethylamino)-4-methoxy-6-(10-(methoxymethoxy)decyl)pyrimidin-5-ol in 5 mL of methanol were added 2 drops of concentrated HCl. The reaction mixture was stirred at reflux for 16 h. The reaction mixture was concentrated under diminished pressure and the residue was purified by chromatography on a silica gel column (8×1 cm). Elution with 1:2 hexanes-ethyl acetate afforded the expected product as white solid: yield 7 mg (40%); mp: 104-105° C.; silica gel TLC Rf 0.15 (1:2 hexanes-ethyl acetate); 1H NMR (methanol-d4) δ 1.28-1.32 (br m, 10H), 1.49 (m, 2H), 1.64 (m, 2H), 2.76 (dd, 2H, J=7.6, 7.6 Hz), 3.22 (s, 6H), 3.51 (t, 2H, J=6.8 Hz) and 4.07 (s, 3H); 13C NMR (methanol-d4) δ 25.55, 27.49, 27.72, 29.02, 29.03, 29.17, 29.19, 29.31, 32.26, 37.20, 37.20, 54.45, 61.59, 128.10, 146.40, 151.34 and 162.67; mass spectrum (APCI+), m/z 326.2442 (M+H) (C17H32N3O3 requires 326.2444).

Provenance & Evidence