Synthesis of 2,4-pyrimidinediamines
View Patent ↗Disclosed herein are methods for synthesizing 2,4-pyrimidinediamines as well as intermediates used therein.
1. A process for preparing a compound of formula VI:
comprising contacting a compound of formula IV:
with a compound of formula V:
in the presence of an amide,
wherein:
R 3 and R 4 are each independently C 1 -C 6 alkyl; and
X is halogen;
under conditions suitable for forming a compound of formula VI.
2. The process of claim 1 , wherein the compound of formula V is di-tert-butyl chloromethyl phosphate:
3. The process of claim 1 , wherein the conditions sufficient to produce the compound of formula VI comprise:
(i) combining the compound of formula IV with the compound of formula V with a base in a polar solvent; and
(ii) washing a product obtained from (i) in an aqueous base solution.
4. The process of claim 3 , wherein the base in (i) comprises at least one of cesium carbonate (Cs 2 CO 3 ) and potassium carbonate (K 2 CO 3 ); the polar solvent comprises at least one of DMF and N,N-dimethylacetamide (DMAc); and the aqueous base in (ii) comprises at least one of sodium bicarbonate (NaHCO 3 ) and sodium hydroxide (NaOH).
5. The process of claim 1 , wherein the compound of formula VI is not isolated.
6. The process of claim 1 , wherein the compound of formula V is stabilized with N,N-dimethylacetamide (DMAc) solvent.