Tetrahydrofuran → HCID 57526819, compound

HRID 1452629Notes

Reaction equation

HRID 1452629 reaction equation
[O:1]1CCCC1.[CH2:6]([C:9]1[C:10]([Cl:35])=[N:11][C:12]2[N:13]([N:32]=[CH:33][CH:34]=2)[C:14]=1[N:15]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH3:31])=[CH:25][CH:24]=1)[C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH:7]=C.I([O-])(=O)(=O)=O.[Na+].S([O-])([O-])=O.[Na+].[Na+]>[Os](=O)(=O)(=O)=O.O>[C:18]([O:17][C:16](=[O:22])[N:15]([C:14]1[N:13]2[N:32]=[CH:33][CH:34]=[C:12]2[N:11]=[C:10]([Cl:35])[C:9]=1[CH2:6][CH:7]=[O:1])[C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH3:31])=[CH:25][CH:24]=1)([CH3:20])([CH3:19])[CH3:21]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 24437Sodium SulfiteHCID 23667635Sodium periodateHCID 57526828HCID 57526828, compound

Product 1

HCID 57526819HCID 57526819, compound

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent

Procedure

To a mixed solution of tetrahydrofuran (12 mL) and water (3 mL) containing tert-butyl (6-allyl-5-chloropyrazolo[1,5-a]pyrimidin-7-yl)(4-ethoxyphenyl)carbamate (1.5 g, 3.5 mmol), sodium periodate (2.3 g, 10.5 mmol) and osmium tetraoxide (2.5w/v % in tert-butanol, 1.8 mL, 0.15 mmol) were added with ice-cooling. After this mixture was stirred at room temperature for 5 hr, aqueous sodium sulfite was added here. The resultant mixture was extracted with ethyl acetate. The organic layer was washed with aqueous sodium hydrogen carbonate and then brine and dried over sodium sulfate. After the sodium sulfate was filtered off, the solvent was distilled off to obtain tert-butyl[5-chloro-6-(2-oxoethyl)pyrazolo[1,5-a]pyrimidin-7-yl](4-ethoxyphenyl)carbamate.

Workup

  1. additionwere added with ice-
  2. temperaturecooling
  3. extractionThe resultant mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with aqueous sodium hydrogen carbonate
  5. dry with materialbrine and dried over sodium sulfate
  6. filtrationAfter the sodium sulfate was filtered off
  7. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-86cbddd378b6422088e177e988206359
Source dataset
uspto-grants-2009_01
Patent number
US07473694B2

Reaction notes

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