Dimethylformamide → 6-chloro-2-(trifluoromethyl)-7H-purine

Participants

Reaction Steps

A mixture of 15 g (73 mmol) of 2-trifluoromethylhypoxanthine and 300 mL of CHCl3 was warmed to reflux and treated with a solution of 26.7 mL (366 mmol) SOCl2 and 28.3 mL (366 mmol) DMF. The reaction was maintained at reflux for 1.5 h, cooled to room temperature, and poured into 1.2 L of ice-water. The organic layer was separated and washed with 2×300 mL of H2O. The pH of the combined aqueous phases was adjusted to 7 with saturated NaHCO3 and extracted with 3×1.2 L of ether. The combined ether and chloroform extracts were dried (MgSO4) and concentrated to dryness to give 7.4 g of crude product. 1H NMR (DMSO-d6) δ 14.45 (bs, 1H), 8.95 (s, 1H). MS (ES+) 222.96 (100%, M+H).

Provenance & Evidence