Have you tried looking at the Web.config file for the maxrequestlength tag? The problem in this case is not the upload, but rather the request for the file, when the page is loaded. Look for the following line:
<httpruntime maxrequestlength="51200" executiontimeout="7200"/>
Where I set the second number to 2 hours (just a random timeout time) and the first number is the maximum file size that a page that needs the file can request. In this case, you can have 500Mb of upload size. This may fix it, however, there's also another section that you can edit, added in for security purposes:
<security>
<requestFiltering>
<requestLimits maxAllowedContentLength="524288000"/>
</requestFiltering>
</security>
Here, again you have 1024x1024*500=500Mb. This is edited in the session properties - you can do that through the Management Interface or through writing your own scripts. Have a look at MSDN here:
http://technet.microsoft.com/en-us/library/cc725820(v=ws.10).aspx