I don't have something that could be of Crafting Interpreters level on hand, but the general suggestion given to this question on DotNetEvolution discord by Roslyn team members was to start with the spec itself:
https://ecma-international.org/publications-and-standards/st...This might be a bit of a learning curve if you don't have experience with writing compilers like that though.
There are other materials that might prove useful should you go down this path:
- A series of blog posts of a student who is writing a Rust to .NET compiler which you could follow along: https://fractalfir.github.io/generated_html/home.html The project itself: https://github.com/FractalFir/rustc_codegen_clr
- A video series on writing a compiler for .NET from scratch: https://www.youtube.com/watch?v=wgHIkdUQbp0&list=PLRAdsfhKI4... Notes: https://github.com/terrajobst/minsk/tree/master/docs
As for CLR via C#, while it has certain facts that remained the same, the ecosystem has changed a lot since then, you really want to target the latest LTS to get best experience and performance. If you liked it, then I can strongly suggest https://github.com/dotnet/runtime/tree/main/docs/design/core... which covers .NET runtime internals.
p.s.: if it's any consolation, the promise in CLR via C# of JIT having the advantage of dynamically profiling code execution and compiling to profile-guided version, tuned to the exact hardware and environment is finally fulfilled, many years later :)