1,1'-Carbonyldiimidazole → HCID 86694158, compound

Participants

Reaction Conditions

Reaction Steps

To a heated (50° C.) solution of 6-bromo-N2-cyclopropylpyrazine-2,3-diamine (0.740 g, 3.23 mmol) in THF (20 mL) was added 1,1′-carbonyldiimidazole (1.00 g, 6.17 mmol) in one portion. The reaction was then heated at 66° C. for 3 h. Additional 1,1′-carbonyldiimidazole (1.00 g, 6.17 mmol) was added and the reaction was heated at 50° C. overnight. The reaction was cooled to room temperature and carefully quenched with water (slight exotherm) until gas evolution ceased. The solution was diluted with EtOAc and the layer were separated. The organic layer was washed with water (1×) and brine (1×). The solution was evaporated onto silica gel and purified by flash chromatography (ISCO(40 gram)) eluting with EtOAc:hexanes (0:1→2:3) to give 467 mg (57%) of a yellow crystalline solid. ESI MS 256.9 [M+1].

Provenance & Evidence