HCID 86723483, compound → HCID 77107224, compound

HRID 2201247Notes

Reaction equation

HRID 2201247 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([C:7]2[C:15]3[N:11]([C:12]([C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[CH:25]=4)=[C:13]4[C:19](=[O:20])[N:18]([CH3:21])[C:17](=[O:22])[N:16]([CH3:23])[C:14]4=3)[CH2:10][CH:9]([CH2:31][OH:32])[CH:8]=2)[S:5][CH:6]=1>[Pt].C(O)C.O1CCCC1>[Cl:1][C:2]1[N:3]=[C:4]([CH:7]2[C:15]3[N:11]([C:12]([C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[CH:25]=4)=[C:13]4[C:19](=[O:20])[N:18]([CH3:21])[C:17](=[O:22])[N:16]([CH3:23])[C:14]4=3)[CH2:10][CH:9]([CH2:31][OH:32])[CH2:8]2)[S:5][CH:6]=1

Participants

5

Reactant 1

HCID 86723483HCID 86723483, compound

Product 1

HCID 77107224HCID 77107224, compound

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 10-(4-Chlorothiazol-2-yl)-5-(3-fluorophenyl)-8-(hydroxymethyl)-1,3-dimethyl-7,8-dihydropyrimido[4,5-a]indolizine-2,4(1H,3H)-dione (310 mg, 0.66 mmol) and 10% platinum on carbon (310 mg) in ethanol (22 mL) and tetrahydrofuran (22 mL) was stirred under an atmosphere of hydrogen for 3 days. The reaction mixture was filtered and the filtrates concentrated under vacuum. The residue was dissolved in ethanol (22 mL) and tetrahydrofuran (22 mL), fresh 10% platinum on carbon (310 mg) was added and the mixture further stirred under an atmosphere of hydrogen for 5 days. The reaction mixture was filtered and the filtrates evaporated under vacuum. The residue was dissolved in 10 mL of 5% MeOH/DCM and the solution was treated with silica-TMT (trimercaptotriazine functionalized silica, ˜1 g) for 5 minutes, then filtered. The residue was washed with 5% MeOH/DCM and the filtrates evaporated under vacuum.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrates concentrated under vacuum
  3. dissolutionThe residue was dissolved in ethanol (22 mL)
  4. additiontetrahydrofuran (22 mL), fresh 10% platinum on carbon (310 mg) was added
  5. stirringthe mixture further stirred under an atmosphere of hydrogen for 5 days
  6. filtrationThe reaction mixture was filtered
  7. customthe filtrates evaporated under vacuum
  8. dissolutionThe residue was dissolved in 10 mL of 5% MeOH/DCM
  9. additionthe solution was treated with silica-TMT (trimercaptotriazine functionalized silica, ˜1 g) for 5 minutes
  10. filtrationfiltered
  11. washThe residue was washed with 5% MeOH/DCM
  12. customthe filtrates evaporated under vacuum

Sources & evidence

ORD record
ord-d34e4e55bc904a88a4f6ba0a27f50329
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

Loading…