Novel triazolo pyrimidine compounds

Abstract

The present invention relates to a pyrimidine compound (I) useful as a pharmaceutical intermediate, to a process for preparing said pyrimidine compound, to intermediates used in said process, and to the use of said pyrimidine compound in the preparation of pharmaceuticals.

1 . A compound of formula (I):  
       
         
           
           
               
               
           
         
       
     
     
         2 . A process for preparing a compound of formula (I), comprising reacting a compound of formula (II):  
       
         
           
           
               
               
           
         
         with a salt of a compound of formula (III):  
         
           
             
             
                 
                 
             
           
         
       
     
     
         3 . A process for preparing a compound of formula (I) as claimed in  claim 2  comprising hydrogenating a compound of formula (IV):  
       
         
           
           
               
               
           
         
         wherein Ar is phenyl optionally substituted by halogen, C 1-4  alkyl or C 1-4  alkoxy; to give a compound of formula (II), and reacting the compound of formula (II) with a compound of formula (III) to provide the compound of formula (I).  
       
     
     
         4 . A process for preparing a compound of formula (II):  
       
         
           
           
               
               
           
         
         comprising hydrogenating a compound of formula (IV):  
         
           
             
             
                 
                 
             
           
         
         wherein Ar is phenyl optionally substituted by halogen, C 1-4  alkyl or C 1-4  alkoxy.  
       
     
     
         5 . A process for preparing a compound of formula (II) as claimed in  claim 2 , comprising chlorinating a compound of formula (VIII):  
       
         
           
           
               
               
           
         
         wherein Ar is phenyl optionally substituted by halogen, C 1-4  alkyl or C 1-4  alkoxy, to provide a compound of formula (IV), and then hydrogenating the compound of formula (IV).  
       
     
     
         6 . The use of a compound of formula (I) to prepare a compound of formula (A):  
       
         
           
           
               
               
           
         
         comprising:  
         (a) reacting a compound of formula (I) with an alkali metal nitrite in the presence of a suitable acid to prepare a compound of formula (VII):  
         
           
             
             
                 
                 
             
           
         
         (b) coupling the compound of formula (VII) with a compound of formula (VI):  
         
           
             
             
                 
                 
             
           
         
         to provide a compound of formula (V):  
         
           
             
             
                 
                 
             
           
         
         and,  
         (c) deprotecting a compound of formula (V) to provide the compound of formula (A).  
       
     
     
         7 . A process for preparing a salt of a compound of formula (III):  
       
         
           
           
               
               
           
         
         comprising reacting a compound of formula (III) with the necessary acid.  
       
     
     
         8 . A process for preparing a salt of a compound of formula (III): comprising the steps:  
       
         
           
           
               
               
           
         
         (a) preparing a compound of formula (XI):  
         
           
             
             
                 
                 
             
           
         
         by reacting a compound of formula (XII):  
         
           
             
             
                 
                 
             
           
         
         with benzyl chloroformate;  
         (b) preparing a compound of formula (X):  
         
           
             
             
                 
                 
             
           
         
         by reacting a compound of formula (XI) with a compound L-CH 2 CO 2 R* {wherein R* is C 1-4 alkyl; and L is a leaving group};  
         (c) preparing a compound of formula (IX):  
         
           
             
             
                 
                 
             
           
         
         by reducing a compound of formula (X);  
         (d) preparing a compound of formula (III):  
         
           
             
             
                 
                 
             
           
         
         by deprotecting a compound of formula (IX); and,  
         (e) preparing a salt of a compound of formula (III) by reacting the compound of formula (III) with the necessary acid.  
       
     
     
         9 . An intermediate compound of formula (II), (IV), (VII), (VIII), (X) or (XI) or a salt of a compound of formula (III).