Dimethyl Sulfate → HCID 86723488, compound

HRID 2201251Notes

Reaction equation

HRID 2201251 reaction equation
[CH3:1][N:2]1[C:7]2=[C:8]3[N:13]([C:14]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)=[C:6]2[C:5](=[O:25])[N:4]([CH3:26])[C:3]1=[O:27])[C@H:12]([C:21]([OH:23])=[O:22])[CH2:11][CH2:10][C:9]3=[O:24].[C:28](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O>CC(C)=O.O>[CH3:1][N:2]1[C:7]2=[C:8]3[N:13]([C:14]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)=[C:6]2[C:5](=[O:25])[N:4]([CH3:26])[C:3]1=[O:27])[C@H:12]([C:21]([O:23][CH3:28])=[O:22])[CH2:11][CH2:10][C:9]3=[O:24]

Participants

6

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 86723487HCID 86723487, compound

Product 1

HCID 86723488HCID 86723488, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

(S)-1,3-Dimethyl-2,4,10-trioxo-5-phenyl-1,2,3,4,7,8,9,10-octahydropyrimido[4,5-a]indolizine-7-carboxylic acid (1.85 g, 5.04 mmol), potassium carbonate (2.088 g, 15.11 mmol) and dimethyl sulfate (1.444 mL, 15.11 mmol) were combined in acetone (50 mL) and water (5 mL). The mixture was heated at reflux for 1.5 hours, then cooled to room temperature and evaporated under vacuum. The residue was partitioned between DCM and water and the phases separated. The organic phase was passed through a hydrophobic frit and evaporated under vacuum. Purification by chromatography on silica, eluting with 40-80% EtOAc/hexane, afforded the title compound.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 1.5 hours
  3. customevaporated under vacuum
  4. customThe residue was partitioned between DCM and water
  5. customthe phases separated
  6. customevaporated under vacuum
  7. customPurification by chromatography on silica
  8. washeluting with 40-80% EtOAc/hexane

Sources & evidence

ORD record
ord-73dcccbba3ee40149fbc1d8b9e437301
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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