Diethyl Ether → HCID 77105800, compound

HRID 2201179Notes

Reaction equation

HRID 2201179 reaction equation
[CH3:1][N:2]1[C:7]2=[C:8]3[N:13]([C:14]([C:15]4[CH:16]=[C:17]([CH3:21])[CH:18]=[CH:19][CH:20]=4)=[C:6]2[C:5](=[O:28])[N:4]([CH3:29])[C:3]1=[O:30])[CH2:12][CH2:11][CH:10]=[C:9]3[C:22]1[S:23][CH:24]=[C:25]([CH3:27])[N:26]=1.[H][H].C(OCC)C>C(OCC)(=O)C.[Pt]>[CH3:1][N:2]1[C:7]2=[C:8]3[N:13]([C:14]([C:15]4[CH:16]=[C:17]([CH3:21])[CH:18]=[CH:19][CH:20]=4)=[C:6]2[C:5](=[O:28])[N:4]([CH3:29])[C:3]1=[O:30])[CH2:12][CH2:11][CH2:10][CH:9]3[C:22]1[S:23][CH:24]=[C:25]([CH3:27])[N:26]=1

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 86723424HCID 86723424, compound2×HCID 178418361HCID 178418361, compound

Product 1

HCID 77105800HCID 77105800, compound

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

1,3-Dimethyl-10-(4-methylthiazol-2-yl)-5-m-tolyl-7,8-dihydropyrimido[4,5-a]indolizine-2,4(1H,3H)-dione (Intermediate M) (100 mg, 0.24 mmol) was dissolved in ethyl acetate (20 mL) and the resulting solution was hydrogenated using the H-Cube® (10% platinum on carbon CatCart®), at atmospheric pressure of hydrogen and 20° C., for 6.5 hours. The solvent was removed under vacuum. The crude material was purified by chromatography on silica, eluting with 1-2% MeOH/DCM to obtain a gum. Diethyl ether was added and removed under vacuum to give the title compound as a solid.

Workup

  1. customThe solvent was removed under vacuum
  2. customThe crude material was purified by chromatography on silica
  3. washeluting with 1-2% MeOH/DCM
  4. customto obtain a gum
  5. customremoved under vacuum

Sources & evidence

ORD record
ord-f6ea4729e747455ba90d134adbcc95b3
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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