Tetrahydrofuran → HCID 22046287, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 2-amino-6-chloropyrazine (130 mg, 1 mmol) in 3 mL THF at 0° C. under nitrogen was added methyl magnesium iodide (3M in Et2O, 330 μL, 1 mmol) to give a yellow suspension that was stirred at 0° C. for 15 minutes. The suspension was treated with the isocyanate neat (147 μL, 1 mmol) and allowed to warm to room temperature overnight. The reaction was partitioned between EtOAc (30 mL) and 10% Na2CO3 (30 mL). The organics were isolated and washed 1×30 mL with 10% Na2CO3 and 1×30 mL with saturated NaCI. The organics were dried (MgSO4), filtered and concentrated to a crude residue that was triturated with EtOAc to give, after filtration, the urea product as a white solid (27 mg, 9%). 1H-NMR (400 MHz, CDCl3) δ 8.26 (s, 1H), 8.23 (s, 1H), 8.17 (s, 1H), 8.09 (br s, 1H), 6.84 (d, 1H), 6.81 (d, 1H), 3.96 (s, 3H), 2.35 (s, 3H). LRMS (ESI, Positive) m/e 293.0 (M+1).

Provenance & Evidence