10-phenyl-2,3-dihydroimidazo[1,2-a]pyrido[2,3-d]pyrimidin-5(10H)-one → 10-phenyl-2,3,6,7,8,9-hexahydroimidazo[1,2-a]-pyrido[2,3-d]pyrimidin-5(10H)-one
Reaction equation
[C:1]1([N:7]2[C:12]3[N:13]=[CH:14][CH:15]=[CH:16][C:11]=3[C:10](=[O:17])[N:9]3[CH2:18][CH2:19][N:20]=[C:8]23)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>[Pd].C(O)(=O)C>[C:1]1([N:7]2[C:12]3[NH:13][CH2:14][CH2:15][CH2:16][C:11]=3[C:10](=[O:17])[N:9]3[CH2:18][CH2:19][N:20]=[C:8]23)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1Participants
4
Procedure
Hydrogenate a mixture of 10% Pd/C (2.5 g), 10-phenyl-2,3-dihydroimidazo[1,2-a]pyrido[2,3-d]pyrimidin-5(10H)-one (5 g) and glacial acetic acid (125 ml) at 60 psi in a Paar apparatus for 24 hrs. at 25° C. Filter the mixture and evaporate the solvent of the filtrate. Dissolve the residue in 1N NaHCO3 (50 ml), neutralize with additional solid NaHCO3 and extract with CHCl3. Wash combined extracts with H2O, dry and filter. Evaporate solvent of the filtrate and crystallize the residue from EtOAc--MeOH to give 10-phenyl-2,3,6,7,8,9-hexahydroimidazo[1,2-a]-pyrido[2,3-d]pyrimidin-5(10H)-one, m.p. 248.0°-250.5° C.