How long should I be routinely sitting my super strong-willed 3.5 yo down on the potty -- until it finally clicks for him to not pee in his underwear??

How long should I be routinely putting my 3.5 yo on the potty - days, weeks, months?? I've been routinely sitting him down on the potty every 45 min - 1 hr and he doesn't give a crap that his underwear gets completely soaked. He'll pee in the potty sometimes but he will pee in his underwear, too. It's been over a week of sitting him down on the potty every hour. It's not clicking for him to NOT pee in his underwear and to pee in the potty instead.... nothing works with this kid. Not even having a big brother help him.