WO2010002774: Process for the preparation of substituted pyrimidine derivatives

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Biological target:

Histamine H4 receptor: H4



Steps Conditions Reactions
a NaOH, H2O then Benzyl chloroformate, CH2Cl2 Amine protection (CBz protection)
b H2, 10% Pd/C, H2O, AcOH (300 psi) 35oC or H2, 5% Rh/C, H2O, 50oC Pyridine reduction (piperidine formation)
c HCHO, H2, 35oC Reductive amination
d PL-TPP resin, DIAD, THF Mitsunobu reaction
e H2, Pd/C, EtOH (60 psi) Hydrogenolysis (CBz deprotection)
f 2N HCl
g Triethyl orthoformate, anhydride acetic, 95-115oC  
h Sodium ethoxide, EtOH, 80oC Pyrimidine formation