Water → HCID 14416594, compound

Participants

Reaction Steps

To a suspension of dimethyl 2-methyl-1H-imidazole-4,5-dicarboxylate (2 g, 10.1 mmol, prepared according to J. Med. Chem. 1989, 32, 119) in DMF (20 mL) was added under a nitrogen atmosphere potassium tert-butoxide (1.25 g, 11.1 mmol) at room temperature. The mixture was stirred for 15 min and iodomethane (694 μL, 11.1 mmol) was added. The reaction mixture was stirred for 2 h at the same temperature. The reaction mixture was poured into water (75 mL) and extracted with ethyl acetate (2×100 mL). The organic phase was washed water (3×50 mL) and brine (20 mL), dried and concentrated in vacuo to give 720 mg of crude product. The combined aqueous phases were back-extracted dichloromethane (4×50 mL), dried over MgSO4 and concentrated in vacuo to give another 1.4 g of crude product. The combined crude material was purified by flash chromatography (using silica gel and a MeOH/dichloromethane gradient) to give the product as colorless oil (1.89 g, 8.91 mmol, 88.3%). MS: M=213.1 (M+H)+

Provenance & Evidence