Prodrugs of 2,4 pyrimidinediamine compounds and their uses
View Patent ↗The present disclosure provides the 2,4-pyrimidinediamine compound shown below, compositions comprising the compound, intermediates and methods for synthesizing the compound, and methods of using the compound in a variety of applications including treatment of autoimmune diseases.
1. A method of making a compound according to formula 3, and salts thereof, comprising:
(a) reacting compound 1:
with di-tert-butyl chloromethyl phosphate under conditions to make compound 2:
(b) exposing 2 to an acid to give compound 3; and
(c) exposing 3 to an aqueous base.
2. The method of claim 1 , wherein the said conditions in (a) comprise a base.
3. The method of claim 2 , wherein the base is cesium carbonate.
4. The method of claim 2 , wherein the said conditions in (a) further comprise an organic solvent.
5. The method of claim 4 , wherein the organic solvent is dimethylformamide.
6. The method of claim 1 , wherein the acid in (b) is acetic acid.
7. The method of claim 1 , wherein the aqueous base in (c) is a sodium ion containing base.
8. The method of claim 7 , wherein the sodium ion containing base is employed to form a disodium salt of compound 3.