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

HRID 4267Notes

Reaction equation

HRID 4267 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]=1

Participants

4

Reactant 1

HCID 2015218410-phenyl-2,3-dihydroimidazo[1,2-a]pyrido[2,3-d]pyrimidin-5(10H)-one

Product 1

HCID 2015218910-phenyl-2,3,6,7,8,9-hexahydroimidazo[1,2-a]-pyrido[2,3-d]pyrimidin-5(10H)-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

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.

Workup

  1. customat 25° C
  2. filtrationFilter the mixture
  3. customevaporate the solvent of the filtrate
  4. dissolutionDissolve the residue in 1N NaHCO3 (50 ml)
  5. extractionextract with CHCl3
  6. washWash
  7. customdry
  8. filtrationfilter
  9. customEvaporate solvent of the filtrate and crystallize the residue from EtOAc

Sources & evidence

ORD record
ord-87003c6c45064e96a5879078c6f45037
Source dataset
uspto-grants-1988_02
Patent number
US04725596

Reaction notes

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