Formaldehyde → HCID 67329641, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution containing 334 mg (1.17 mmol) of 5-(benzyloxy)-4-methyl-6-pentylpyrimidin-2-amine in 4 mL of methanol were added 4 mL of 35% aq. formaldehyde followed by 588 mg (9.35 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 150 mg (41%); silica gel TLC Rf 0.7 (2:1 hexanes-ethyl acetate); 1H NMR (CDCl3) δ 0.88 (t, 3H, J=7.2 Hz), 1.33 (m, 4H), 1.69 (quint, 2H, J=7.6 Hz), 2.32 (s, 3H), 2.62 (dd, 2H, J=8.0, 8.0 Hz), 3.15 (s, 6H), 4.70 (s, 2H) and 7.33-7.44 (m, 5H); 13C NMR (CDCl3) δ 14.00, 19.31, 22.54, 27.52, 31.67, 31.81, 37.22, 37.22, 75.73, 127.94, 128.13, 128.13, 128.55, 128.55, 137.15, 141.26, 158.60, 160.01 and 163.48; mass spectrum (APCI), m/z 314.2224 (M+H)1 (C19H28N3O requires 314.2232).

Provenance & Evidence