Sodium Hydroxide → HCID 22732477, compound

Participants

Reaction Steps

To a solution of 4-(2-methyl,5-nitroanilino)-2-(3-pyridinyl)-6-(trifluoromethyl)pyrimidine (75 mg, 0.200 mmol) in anhydrous ethanol (10 ml) was added slowly anhydrous tin chloride (152 mg, 0.800 mmol). The mixture was refluxed for 1 h and then rotary evaporated to leave a brown oil. The brown oil was basified with 2N NaOH to give a final pH of 8. The resulting precipitate was filtered and washed with ethyl acetate. The aqueous phase and organic phase was combined, washed with water (1×20 ml) and dried over anhydrous sodium sulfate. The ethyl acetate was rotary evaporated to dryness to give a dark yellow solid (33 mg, 44%). 1H NMR (CDCl3): 9.69-9.68 (m, 1H), 8.73-8.67 (m, 2H), 7.53 (s, 1H), 7.43-7.39 (m, 1H), 7.11 (d, J=8.4 Hz, 1H), 6.72 (s, 1H), 6.64 (d, J=2.7 Hz, 1H), 6.61 (s, 1H), 3.01 (bs, 2H), 2.17 (s, 3H).

Provenance & Evidence