Tetrahydrofuran → 2-(5,7-Dichloropyrazolo[1,5-a]pyrimidin-6-yl)acetaldehyde

HRID 1452615Notes

Reaction equation

HRID 1452615 reaction equation
C1C[O:4]CC1.[CH2:6]([C:9]1[C:10]([Cl:19])=[N:11][C:12]2[N:13]([N:16]=[CH:17][CH:18]=2)[C:14]=1[Cl:15])[CH:7]=C.I([O-])(=O)(=O)=O.[Na+].S([O-])([O-])=O.[Na+].[Na+]>[Os](=O)(=O)(=O)=O.O>[Cl:19][C:10]1[C:9]([CH2:6][CH:7]=[O:4])=[C:14]([Cl:15])[N:13]2[N:16]=[CH:17][CH:18]=[C:12]2[N:11]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 24437Sodium SulfiteHCID 23667635Sodium periodateHCID 575268456-Allyl-5,7-dichloropyrazolo[1,5-a]pyrimidine

Product 1

HCID 866137832-(5,7-Dichloropyrazolo[1,5-a]pyrimidin-6-yl)acetaldehyde

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent

Procedure

To a mixed solution of THF (24 mL) and water (6 mL) containing 6-allyl-5,7-dichloropyrazolo[1,5-a]pyrimidine (1.82 g, 7.89 mmol), sodium periodate (5.12 g, 23.9 mmol) and osmium tetraoxide (2.5w/v % in tert-butanol, 3 mL, 0.23 mmol) were added with ice-cooling. After this mixture was stirred at room temperature for 3 hr, aqueous sodium sulfite was added here. The resultant mixture was extracted with ethyl acetate and 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 5,7-dichloro-6-(2-oxoethyl)pyrazolo[1,5-a]pyrimidine.

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-4593c2454b6148dcb859fd46d5e0cbac
Source dataset
uspto-grants-2009_01
Patent number
US07473694B2

Reaction notes

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