Dimethyl Sulfide → HCID 51049988, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(1-(4-fluorobenzyl)-1H-imidazol-4-yl)-3-methoxy-9,9-dimethyl-6,7-dihydropyrimido[2,1-c][1,4]oxazin-4(9H)-one (0.042 g, 0.109 mmol, 1.0 equiv) in dichloroethane (1.1 mL) under a nitrogen atmosphere, was added BBr3.SMe2 (0.137 g, 0.437 mmol, 4.0 equiv). The reaction was then heated to 80° C. (oil bath). After stirring 1 h, the reaction was cooled to ambient temperature and cautiously quenched with water (5 mL). The mixture was poured into saturated aqueous solution of NaHCO3 and extracted with CH2Cl2 (×3). The combined CH2Cl2 extracts were dried (Na2SO4) and then concentrated in vacuo. The crude product was purified by reverse phase preparatory HPLC to provide the title compound (0.017 g, 42% yield) as a pale gray solid. 1HNMR (400 MHz, CDCl3) δ ppm 11.34 (s, 1H), 7.59 (d, J=1.01 Hz, 1H), 7.42 (d, J=1.51 Hz, 1H), 7.20 (dd, J=8.69, 5.16 Hz, 2H), 7.05-7.13 (m, 2H), 5.16 (s, 2H), 3.95-4.08 (m, 4H), 1.58 (s, 6H); LCMS (ES+, (M+H)+) m/z 371.24.

Provenance & Evidence