This is similar to the issue asked here in SE before https://sharepoint.stackexchange.com/questions/14649/why-are-user-permissions-set-in-ad-not-updated-immediately-to-sharepoint
but in my case it doesn't work.

I have a SharePoint 2010 Enterprise Portal. Authentication mode is Claims based with NTLM. We have also published the portal via TMG.

I noticed something weird with Active Directory Group membership that doesn't update immediately in SharePoint when a user is removed or added to AD Group.

I have setup a SharePoint Group and added the AD Security group inside this SP Group. Users are added and removed via AD Security Group. I have setup publishing page with unique permission with members in SP group can only access. When I add a user in AD it doesn't get immediately reflected in SharePoint. As mentioned in SE article above it take 24 hours to update. 

I ran this command to set the value to 1 minute(as mentioned in the post above) but no luck. But if I add the users directly to SharePoint Group it works immediately. There is something strange with Active Directory and SharePoint Synchronisation.

> stsadm -o setproperty -propertyname token-timeout -propertyvalue 1

>IISRESET


If I do a IIS Reset then the user permissions are properly updated. I have also set the User Profile service to run every 30 minutes(Incremental update).

Additional Info:
The AD group scope is "Global" and group type is "Security".

Does anyone come across similar issue and fixed it?

Additional references

> http://technet.microsoft.com/en-us/library/cc287917(office.14).aspx

>http://sharepointhacker.com/?p=50

>http://answers.flyppdevportal.com/categories/sharepoint2010/sharepoint2010setup.aspx?ID=7ca0d88e-4de0-4aad-99a9-e7d56219f35d