Sodium sulfate decahydrate → HCID 57786020, compound

HRID 1399263Notes

Reaction equation

HRID 1399263 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([C:31](OC)=[O:32])=[C:12]2[C:16]=1[N:15]=[C:14]1[N:17]([C:21]3[C:26]([Cl:27])=[CH:25][C:24]([O:28][CH3:29])=[CH:23][C:22]=3[Cl:30])[CH2:18][CH2:19][CH2:20][N:13]21.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>O1CCCC1.C(#N)C.C(=O)(O)[O-].[Na+].C(OCC)(=O)C.CS(C)=O>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([CH:31]=[O:32])=[C:12]2[C:16]=1[N:15]=[C:14]1[N:17]([C:21]3[C:22]([Cl:30])=[CH:23][C:24]([O:28][CH3:29])=[CH:25][C:26]=3[Cl:27])[CH2:18][CH2:19][CH2:20][N:13]21

Participants

10

Reactant 4

HCID 62649Sodium sulfate decahydrateHCID 159087TriacetoxyperiodinaneHCID 21226445Aluminium lithium hydrideHCID 57786371HCID 57786371, compound

Product 1

HCID 57786020HCID 57786020, compoundYield 89%

Reagents, catalysts & solvents 5

HCID 679Dimethyl SulfoxideSolventHCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a suspension of lithium aluminum hydride (45.7 mg, 1.20 mmol) in tetrahydrofuran (4 mL) was added a solution of methyl 9-chloro-1-(2,6-dichloro-4-methoxyphenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole-6-carboxylate (177 mg, 0.401 mmol) in tetrahydrofuran (4 mL) at 0° C., and the resultant mixture was stirred at 0° C. for 5 min. After sodium sulfate decahydrate (450 mg) was added at 0° C., the resultant mixture was filtered and concentrated in vacuo to give a crude solid. To a solution of the crude solid in acetonitrile (4 mL) and dimethylsulfoxide (0.8 mL) was added Dess-Martin reagent (204 mg, 0.481 mmol) at room temperature, and the resultant mixture was stirred at room temperature for 20 min, diluted with aqueous sodium bicarbonate and ethyl acetate, filtered and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a 20-50% ethyl acetate/n-hexane gradient mixture to give the title compound as a colorless solid (146 mg, 0.356 mmol, 89%).

Workup

  1. filtrationthe resultant mixture was filtered
  2. concentrationconcentrated in vacuo
  3. customto give a crude solid
  4. filtrationfiltered
  5. extractionextracted with ethyl acetate
  6. washThe combined organic layer was washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by flash column chromatography on silica gel eluting with a 20-50% ethyl acetate/n-hexane gradient mixture

Sources & evidence

ORD record
ord-ce1b12482a434c3d988f605fe80f1a57
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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