Tetrahydrofuran → HCID 57526819, compound

HRID 1452625Notes

Reaction equation

HRID 1452625 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, compoundYield 59%

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 the reaction mixture was stirred at room temperature for 5 hr, aqueous sodium sulfite was added here, and the 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, and the residue was purified with column chromatography (20% ethyl acetate-hexane) to obtain the title compound (895 mg, 2.08 mmol, yield 59%). 1H NMR (CDCl3, 400 MHz) δ(ppm): 9.44 (s, 1H), 8.19 (s, 1H), 7.14 (dt, J=9.8 and 2.9 Hz, 2H), 6.81 (d, J=6.8 Hz, 2H), 6.73 (d, J=2.2 Hz, 1H), 3.98 (q, J=7.1 Hz, 2H), 3.84 (d, J=37.3 Hz, 1H), 1.56 (s, 2H), 1.38 (t, J=7.1 Hz, 3H).

Workup

  1. additionwere added with ice-
  2. temperaturecooling
  3. extractionthe 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
  8. customthe residue was purified with column chromatography (20% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-7f5631a15472477381fc2739784ccec4
Source dataset
uspto-grants-2009_01
Patent number
US07473694B2

Reaction notes

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