Sodium hydride → HCID 131734062, compound

Participants

Reaction Conditions

Reaction Steps

NaH (60% dispersion in mineral oil, 480 mg, 12.0 mmol) was added in portions to a stirring solution of (3-oxa-bicyclo[3.1.0]hexan-6-yl)methanol (570 mg, 5.0 mmol; prepared according to procedures described in WO2012/021591A1) in DMF (40 mL) at room temperature under N2 (g) atmosphere. After 20 min, the mixture was cooled to 0° C., followed by addition N-(3-chloro-4-fluorophenyl)-7-fluoro-6-nitroquinazolin-4-amine 1a (1.54 g, 4.6 mmol, prepared according to Smaill, J. B., et al., Journal of Medicinal Chemistry, 2000, 43, 1380-1397). The reaction was quenched after stirring 30 min at 0° C. by a slow addition of saturated NH4Cl, followed by extraction with EtOAc (100 mL). The organic layer was washed with H2O (2×50 mL), brine (50 mL), dried over MgSO4, and concentrated to a yellow residue 2b, product was used directly for the next step. MS m/z (ESI+), 431 [M+1].

Provenance & Evidence