diff --git a/vyper/ast/nodes.py b/vyper/ast/nodes.py
index ffd442f89a..40535e4b90 100644
--- a/vyper/ast/nodes.py
+++ b/vyper/ast/nodes.py
@@ -1194,9 +1194,6 @@ def evaluate(self, left, right) -> ExprNode:
         if not isinstance(left, type(right)):
             raise UnfoldableNode("Cannot compare different literal types")
 
-        if not isinstance(self.op, (Eq, NotEq)) and not isinstance(left, (Int, Decimal)):
-            raise TypeMismatch(f"Invalid literal types for {self.op.description} comparison", self)
-
         value = self.op._op(left.value, right.value)
         return NameConstant.from_node(self, value=value)
 
diff --git a/vyper/semantics/analysis/local.py b/vyper/semantics/analysis/local.py
index b865c8461a..dac55824d1 100644
--- a/vyper/semantics/analysis/local.py
+++ b/vyper/semantics/analysis/local.py
@@ -727,6 +727,16 @@ def visit_Compare(self, node: vy_ast.Compare, typ: VyperType) -> None:
             self.visit(node.right, rtyp)
 
         else:
+            # TODO: this is unreachable because this would throw when the parent node
+            # calls `validate_expected_type`
+            left = get_folded_value(node.left)
+            if not isinstance(node.op, (vy_ast.Eq, vy_ast.NotEq)) and not isinstance(
+                left, (vy_ast.Int, vy_ast.Decimal)
+            ):
+                raise TypeMismatch(
+                    f"Invalid literal types for {node.op.description} comparison", node
+                )
+
             # ex. a < b
             cmp_typ = get_common_types(node.left, node.right).pop()
             if isinstance(cmp_typ, _BytestringT):
diff --git a/vyper/semantics/analysis/pre_typecheck.py b/vyper/semantics/analysis/pre_typecheck.py
index c0d1c90403..88aeca20bc 100644
--- a/vyper/semantics/analysis/pre_typecheck.py
+++ b/vyper/semantics/analysis/pre_typecheck.py
@@ -179,7 +179,10 @@ def visit_BoolOp(self, node):
 
         values = [get_folded_value(i) for i in node.values]
         if all(isinstance(v, vy_ast.NameConstant) for v in values):
-            node._metadata["folded_value"] = node.evaluate(values)
+            try:
+                node._metadata["folded_value"] = node.evaluate(values)
+            except UnfoldableNode:
+                pass
 
     def visit_Call(self, node):
         for arg in node.args:
@@ -230,9 +233,11 @@ def visit_Compare(self, node):
             node._metadata["folded_value"] = node.evaluate(left, right)
             return
 
-        right = get_folded_value(node)
-        if isinstance(left, type(right)) and isinstance(left, (vy_ast.Int, vy_ast.Decimal)):
+        right = get_folded_value(node.right)
+        try:
             node._metadata["folded_value"] = node.evaluate(left, right)
+        except UnfoldableNode:
+            pass
 
     def visit_Constant(self, node):
         pass