Dimethylformamide → HCID 67329637, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution containing 1.0 g (7.19 mmol) of 4-methoxy-6-methylpyrimidin-2-amine in 10 mL of anf DMF were added 1.35 mL (21.6 mmol) of methyl iodide followed by 853 mg (21.6 mmol) of 60% suspension of sodium hydride in mineral oil. The reaction mixture was stirred at 23° C. for 20 min. The reaction mixture was quenched with water and concentrated under diminished pressure in order to remove as much DMF as possible. The residue was dissolved in 70 mL of ethyl acetate and washed with 50-mL portions of water and brine respectively. The organic solution was dried (MgSO4) and concentrated under diminished pressure. The residue was purified by chromatography on a silica gel column (15×5 cm). Elution with 4:1 hexanes-ethyl acetate afforded the expected product as colorless oil: yield 755 mg (63%); silica gel TLC Rf 0.25 (4:1 hexanes-ethyl acetate); 1H NMR (CDCl3) δ 2.22 (s, 3H), 3.12 (s, 6H), 3.83 (s, 3H) and 5.76 (s, 1H); 13C-NMR (CDCl3) δ 24.07, 36.76, 36.76, 52.68, 93.74, 162.24, 167.70 and 170.24; mass spectrum (APCI+), m/z 168.1135 (M+H) (C8H14N3O requires 168.1137).

Provenance & Evidence