Tetrahydrofuran → HCID 19017756, compound

Participants

Reaction Steps

To ethyl 4-amino-1-methyl-2-(methylthio)imidazole-5-carboxylate (3.014 g, 14.00 mmol), prepared by the method of Gompper et al., Tetrahedron Lett. 1885 (1966), in dimethylformamide (50 mL) at 0° C. was added a solution of 1.0M sodium bis(trimethylsilyl)amide in tetrahydrofuran (14.0 mL, 14.0 mmol). After 1 hour, 1-iodobutane (1.75 mL, 15.4 mmol) was added and the reaction was stirred at ambient temperature for 18 hours. The mixture was diluted with ethyl acetate, washed with water and brine, dried over sodium sulfate and evaporated under reduced pressure. Chromatography of the residue on silica gel eluting with 5% ethyl acetate in hexane afforded 2.706 g (71%) of the desired product as an oil. TLC (10% ethyl acetate/90% hexane) Rf =0.24. 1H NMR (CDCl3, 300 MHz) d 0.94 (t, 3H), 1.34 (t, 3H), 1.35-1.65 (m, 4H), 2.62 (s, 3H), 3.38-3.49 (m, 2H), 3.66 (s, 3H), 4.28 (q, 2H), 5.58 (br s, 1H). MS (DCl/NH3) m/e 272 (M+H)+.

Provenance & Evidence