Formaldehyde → HCID 67328276, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution containing 305 mg (0.86 mmol) of 5-(benzyloxy)-4-decyl-6-methylpyrimidin-2-amine in 3 mL of methanol were added 3 mL of 35% aq. formaldehyde followed by 271 mg (4.30 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 2:1 hexanes-ethyl acetate afforded the expected product as colorless oil: yield 154 mg (46%); silica gel TLC Rf 0.8 (2:1 hexanes-ethyl acetate); 1H NMR (CDCl3) δ 0.87 (t, 3H, J=6.4 Hz), 1.33 (m, 14H), 1.69 (quint, 2H, J=7.2 Hz), 2.32 (s, 3H), 2.61 (dd, 2H, J=7.6, 7.6 Hz), 3.14 (s, 6H), 4.70 (s, 2H) and 7.33-7.44 (m, 5H); 13C NMR (CDCl3) δ 14.07, 19.29, 22.65, 27.85, 29.30, 29.50, 29.55, 29.59, 29.62, 31.71, 31.89, 37.21, 37.21, 75.72, 127.91, 128.11, 128.11, 128.54, 128.54, 137.17, 141.27, 158.60, 159.01 and 163.49; mass spectrum (APCI), m/z 384.3003 (M+H)+ (C24H38N3O requires 384.3015).

Provenance & Evidence