Process for making hydroxylated cyclopentylpyrimidine compounds

Abstract

and salts thereof, wherein R1 is defined herein, and compounds and intermediates of said formula.

1 . (canceled) 
     
     
         2 . A compound of formula II or formula III: 
       
         
           
           
               
               
           
         
         or a salt thereof, wherein: 
         R 1  is tert-butoxycarbonyl; 
         R 2  is —CN, —COOR a  or —CONR a R b ; 
         R a  and R b  are independently hydrogen, —OR c , substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted phenyl or substituted or unsubstituted heterocyclyl; or 
         R a  and R b  are taken together with the atom to which they are attached to form a 3-7 membered heterocyclyl; 
         R c  is independently hydrogen or optionally substituted C 1-12  alkyl; 
         M is Li or Mg; and 
         R 3  is bromo or iodo. 
       
     
     
         3 . The compound of  claim 2 , wherein R 2 —COOR a  or —CONR a R b . 
     
     
         4 . The compound of  claim 2 , wherein R 2  is —COOH or —COOCH 3 . 
     
     
         5 . The compound of  claim 2 , wherein R 2  is —C(O)N(CH 3 )OCH 3 . 
     
     
         6 . The compound of  claim 2 , wherein R 3  is bromo. 
     
     
         7 . The compound of  claim 2 , that is a compound of formula II: 
       
         
           
           
               
               
           
         
         or a salt thereof. 
       
     
     
         8 . The compound of  claim 7 , wherein M is Mg. 
     
     
         9 . The compound of  claim 7 , wherein R 2  is —COOH or —COOCH 3 . 
     
     
         10 . The compound of  claim 7 , wherein R 2  is —C(O)N(CH 3 )OCH 3 . 
     
     
         11 . The compound of  claim 7 , wherein R 2  is —COOCH 3 . 
     
     
         12 . The compound of  claim 2  that is a compound of formula III: 
       
         
           
           
               
               
           
         
         or a salt thereof. 
       
     
     
         13 . The compound of  claim 12 , wherein R 2  is —COOH or —COOCH 3 . 
     
     
         14 . The compound of  claim 12 , wherein R 2  is —C(O)N(CH 3 )OCH 3 . 
     
     
         15 . The compound of  claim 12 , wherein R 3  is bromo.