Sodium Hydroxide → 3-Iodo-5-methoxy-2-(tetrahydro-pyran-4-yl)-pyridin-4-ylamine

Participants

Reaction Steps

To a stirred solution of 590 mg (2.66 mmol) 5-methoxy-2-(tetrahydro-pyran-4-yl)-pyridin-4-ylamine in 3 ml 65% aqueous sulfuric acid heated to 100° C. was added 728 mg (3.40 mmol) potassium iodate and stirring continued for 2 h at 100° C. The mixture was then cooled in an ice-bath before being made basic by addition of 5 N aqueous sodium hydroxide solution. The mixture was extracted three times with tetrahydrofuran and the combined organic phases were dried over sodium sulfate and concentrated in vacuo. Flash chromatography (ethyl acetate/hexane/triethylamine) afforded 516 mg (58%) 3-iodo-5-methoxy-2-(tetrahydro-pyran-4-yl)-pyridin-4-ylamine as a yellow crystalline solid. ES-MS m/e (%): 335 (M+H+, 100).

Provenance & Evidence