Toluene → HCID 10644860, compound

Participants

Reaction Steps

To a mixture of 2-(4-t-butylphenyl)-4H-thieno[3,2-d]-[1,3]oxazin-4-one (400 mg, 1.4 mmol), 3-aminobenzonitrile (165 mg, 1.4 mmol) and THF (5 mL) was added 0.5 M potassium hexamethyldisilazide in toluene (3.08 mL, 1.54 mmol) and stirred for 15 min. The reaction was added NH4Cl and ethyl acetate. The organic layer was washed with water (3×) and brine, MgSO4 dried and concentrated. The residue was chromatographed (20% THF/hexanes) to give the title compound as a solid (580 mg, 51%); 1.37 (s, 9H), 7.47 (m, 4H), 7.57 (d, 2H, J=8.4 HZ); 7.68 (m, 1H), 7.98 (d, 2H, J=8.4 Hz); 8.20 (s, 1H); 8.42 (d, 1H, J=5.7 Hz); 11.80 (s, 1H); MS(FD): 403.

Provenance & Evidence