HCID 86723475, compound → HCID 77107223, compound

HRID 2201241Notes

Reaction equation

HRID 2201241 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:28]=[CH:27][N:26]([CH3:29])[N: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][CH2:9][CH:8]=2)[S:5][CH:6]=1>[Pt].C(O)C.C1COCC1>[Cl:1][C:2]1[N:3]=[C:4]([CH:7]2[C:15]3[N:11]([C:12]([C:24]4[CH:28]=[CH:27][N:26]([CH3:29])[N: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][CH2:9][CH2:8]2)[S:5][CH:6]=1

Participants

5

Reactant 1

HCID 86723475HCID 86723475, compound

Product 1

HCID 77107223HCID 77107223, compound

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 10-(4-chlorothiazol-2-yl)-1,3-dimethyl-5-(1-methyl-1H-pyrazol-3-yl)-7,8-dihydropyrimido[4,5-a]indolizine-2,4(1H,3H)-dione (25 mg, 0.058 mmol) and 10% platinum on carbon (12 mg, 6.15 μmol) in ethanol (2.2 ml) and THF (6.6 ml) was stirred under an atmosphere of hydrogen for 7 days. The mixture was filtered and the residue rinsed thoroughly with ethanol and the combined filtrates evaporated under vacuum. Purification by chromatography on silica, eluting with 80% EtOAc/hexane afforded a crude material which was triturated with diethyl ether to afford the title compound.

Workup

  1. filtrationThe mixture was filtered
  2. washthe residue rinsed thoroughly with ethanol
  3. customthe combined filtrates evaporated under vacuum
  4. customPurification by chromatography on silica
  5. washeluting with 80% EtOAc/hexane
  6. customafforded a crude material which
  7. customwas triturated with diethyl ether

Sources & evidence

ORD record
ord-426e6163993d4a9791639c0c5260dd6b
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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