I think your problem is in the notation conventions.
If you write everything in terms of functions the problem disappears. Suppose the area at time $t$ is $A(t)$ and the radius at time $t$ is $r(t)$. Those two functions are related:
$$
A(t) = \pi r(t)^2.
$$
Differentiating with respect to $t$, using the chain rule on the right:
$$
A'(t) = 2 \pi r(t) r'(t) .
$$
Then the substitutions you make are straightforward and routine:
$$
5 = 2 \pi \times 5 \times r'(t) .
$$
Then solve that for $r'(t)$. (You don't know and can't find out what time that actually happens, but you don't care.)
If you want to use the differential notation (which is valuable and worth knowing how to do correctly) you should think of "$dr$" as "a little bit of $r$", not as "$d$ times the value of $r$".
Then the equation
$$
(dA) = 2 \pi r (dr)
$$
tells you the relationship between a small change in the radius and a small change in the area. That makes geometric sense if you think of surrounding a circle of radius $r$ by an annulus of width $dr$ and seeing how the area changes.
Dividing by a small change $dt$ in $t$ turns those small changes into instantaneous rates of change.