Sodium hydride → HCID 58382232, compound

Participants

Reaction Steps

To a round bottom flask was added 5-bromo-3-((4-methoxyphenyl)ethynyl)pyrazin-2-amine (11.9 g, 39.1 mmol, prepared using A from 1-ethynyl-4-methoxybenzene with 3,5-dibromopyrazin-2-amine), DMF (98 mL) and NaH (60% in mineral oil) (2.03 g, 50.8 mmol). The reaction mixture was stirred at room temperature for about 2 h and then 2-(trimethylsilyl)ethoxymethyl chloride (7.63 mL, 43.0 mmol) was added. The reaction mixture was stirred at rt for about 2 h. To the reaction mixture was added NaH (60% in mineral oil) (0.469 g, 19.55 mmol). The reaction mixture was stirred for about 24 h at rt. The reaction mixture was quenched with water (400 mL) and extracted with EtOAc (3×250 mL). The organic layer was washed with brine (250 mL), dried with MgSO4, filtered and concentrated in vacuo. The crude material was purified by flash chromatography (300 g Silicycle® column, DCM/MeOH 1:0 to 10:1) to give the title compound (14.3 g; 84%): LC/MS (Table 2, Method b) Rt=3.11 min; MS m/z 436.2 (M+H)+.

Provenance & Evidence