Sodium hydride → HCID 85873129, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of N-(2-hydroxyethyl)morpholine (1.09 g, 8.27 mmol) in N,N-dimethylformamide (5 mL) was added sodium hydride (364 mg, 9.10 mmol, 60% dispersion in oil) in portions. The mixture was stirred at room temperature for 1 h and at 45° C. for 1.5 h. The greenish solution was added dropwise over 5 min to a solution of 4,6-dichloropyrimidine (3.0 g, 20.1 mmol) in N,N-dimethylformamide (5 mL). The solvent was removed in vacuo, and the residue was partitioned between water and ethyl acetate. The organic layer was dried (Na2SO4) and the solvent was removed in vacuo. The crude product was purified on a silica gel column using ethyl acetate as the eluent affording 1.17 g (58% yield) of the title compound as a yellow oil: 1H NMR (CDCl3, 400 MHz) δ 8.57 (s, 1H), 6.80 (s, 1 H), 4.53 (t, J=6 Hz, 2 H), 3.72 (t, J=5 Hz, 4 H), 2.77 (t, J=6 Hz, 2 H), 2.55 (t, J=4 Hz, 4 H); 13C NMR (CDCl3, 100 MHz) δ 170.0, 160.7, 158.1, 108.0, 66.9, 64.6, 57.1, 53.9; MS (ESP) m/z 244 (M++1).

Provenance & Evidence