Part 1
I wish to show that:
$$E(X)=E[(X|Y=y1)*Pr(Y=y1)+(X|Y=y2)*Pr(Y=y2)]$$
where the random variable Y can take 2 possible values.
As many comments and answers have suggested, this may be technically confusing and ill posed, so as an extension I am posting the motivation for writing something like this:
Suppose I want to calculate $E(S(T))$ Where $S(T)$ represents the stock price at time T. However, it so happens that $T$ is also a random variable, so I want to be able to write this as:
$$E[S(T1)*1(T=T1)+S(T2)*1(T=T2)]$$
Note that $S(T1)$ and $S(T2)$ are still random and are stock prices in the future.