HCID 67354026, compound → HCID 53373259, compound

Participants

Reaction Steps

To a stirred solution containing 240 mg (0.48 mmol) of 5-(Benzyloxy)-2-(2,5-dimethyl-1H-pyrrol-1-yl)-4-(10-(methoxymethoxy)decyl)-6-methylpyrimidine in 10 mL of methanol were two drops of concentrated HCl and the mixture was stirred at reflux overnight. To the mixture were added 10 mg of 20% palladium hydroxide on carbon (Degussa type E101 NE/E). The reaction mixture was stirred at 23° C. under hydrogen atmosphere for 15 min. The reaction mixture was filtered through celite and the filtrated was concentrated under diminished pressure. The residue was purified by chromatography on a silica gel column (13×3 cm). Elution with 2:1 toluene-ethyl acetate afforded the expected product as colorless oil: yield 13 mg (8%); silica gel TLC Rf 0.40 (2:1 toluene-ethyl acetate); 1H NMR (methanol-d4) 61.29-1.35 (m, 12H), 1.49 (m, 2H), 1.71 (m, 2H), 2.11 (s, 6H), 2.45 (s, 3H), 2.80 (dd, 2H, J=7.2, 7.2 Hz), 3.50 (t, 2H, J=6.4 Hz) and ˜5.74 (s, 2H); 13C NMR (methanol-d4) δ 11.96, 11.96, 17.50, 25.49, 27.27, 28.93, 29.05, 29.12, 29.18, 29.22, 31.00, 32.22, 61.56, 106.34, 106.34, 128.37, 128.37, 146.20, 148.84, 155.40 and 158.94; mass spectrum (APCI), m/z 360.2659 (M+H)+ (C21H34N3O2 requires 360.2651).

Provenance & Evidence