Formamide → HCID 69560135, compound

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Reaction Steps

A mixture of 2-amino-4-trifluoromethylpyrimidine (2.0 g, 12.2 mmol) and N,N-dimethylformamide dimethyl acetal (1.79 ml, 13.5 mmol) in toluene (50 ml) was heated at reflux for 1 h and then concentrated under reduced pressure. The resulting formamide was treated with ethyl bromoacetate (1.49 ml, 13.4 mmol) in toluene (60 ml) at reflux for 12 h and then concentrated under reduced pressure. The product was treated with saturated sodium hydrogencarbonate solution (50 ml) and extracted with EtOAc (3×50 ml). The combined organic extracts were washed with brine (50 ml), dried (MgSO4) and then concentrated while dry loading onto silica. Subsequent purification by column chromatography on silica using diethyl ether gave ethyl 7-trifluoromethylimidazo[1,2-α]pyrimidine-3-carboxylate (2.01 g, 64%): δH (360 MHz, CDCl3) δ 1.45 (3H, t, J 7.1), 4.47 (2H, q, J 7.1), 7.44 (1H, d, J 7.1), 8.60 (1H, s), 9.77 (1H, d, J 7.1); m/z (ES+) 347 (M++H).

Provenance & Evidence