How to Upgrade Windows Server 2008 R2 From Standard to Datacenter

Open a command console or powershell as administrator and run the following

DISM /online /Set-Edition:ServerDataCenter /AcceptEula /Productkey:74YFP-3QFB3-KQT8W-PMXWJ-7M648

The key is a KMS key.

The server will reboot twice.