Formaldehyde → HCID 67328968, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution containing 230 mg (0.52 mmol) of 5-(benzyloxy)-4-hexadecyl-6-methylpyrimidin-2-amine in 4 mL of methanol were added 4 mL of 35% aq. formaldehyde followed by 263 mg (4.18 mmol) of NaCNBH3. The reaction mixture was stirred at 23° C. for 3 h. The reaction mixture was quenched with acetic acid until bubbling ceased then poured into 20 mL of water and extracted with two 40-mL portions of ethyl acetate. The combined organic layer was washed with one 40-mL portion of saturated aq. NaHCO3 and one 40-mL portion of brine. The organic solution was dried (MgSO4) and then concentrated under diminished pressure. The residue was purified by chromatography on a silica gel column (8×3 cm). Elution with 4:1 hexanes-ethyl acetate afforded the expected product as colorless oil: yield 100 mg (41%); silica gel TLC Rf 0.75 (4:1 hexanes-ethyl acetate); 1H NMR (CDCl3) δ 0.86 (t, 3H, J=6.8 Hz), 1.23-1.28 (br m, 26H), 1.68 (quint, 2H, J=6.8 Hz), 2.31 (s, 3H), 2.61 (dd, 2H, J=7.6, 7.6 Hz), 3.14 (s, 6H), 4.69 (s, 2H) and 7.40-7.46 (m, 5H); 13C NMR (CDCl3) δ 14.05, 19.29, 22.64, 27.72, 27.84, 29.31, 29.50, 29.55, 29.62, 29.64, 29.64, 29.64, 29.66, 29.66, 29.66, 31.59, 31.70, 31.89, 37.21, 37.21, 75.67, 127.90, 128.16, 128.16, 128.54, 128.54, 137.17, 141.27, 158.60, 159.01 and 163.62; mass spectrum (APCI), m/z 468.3950 (M+H)+ (C30H50N3O requires 468.3954).

Provenance & Evidence