No, you cannot upload a PDF of a 1099R
Some 1099R's etc can be imported from the financial institutions that issue them. However, they are typically not ready for import until later -- even into February.
To import a 1099R go to Federal>Wages and Income>Retirement Plans and Social Security>IRA,401k, Pension Plan Withdrawals (1099R)
When you are on the screen that says Let's Enter your1099R, choose import from my bank or brokerage You will be able to choose from a list of banks/brokerages, etc.
You will need to know the account and user ID that you normally use to go on the website for that intsitution