Hydrogen Peroxide → HCID 57526810, compound

HRID 1452628Notes

Reaction equation

HRID 1452628 reaction equation
[CH2:1]([C:4]1[C:5]([Cl:30])=[N:6][C:7]2[N:8]([N:27]=[CH:28][CH:29]=2)[C:9]=1[N:10]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH3:26])=[CH:20][CH:19]=1)[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH:2]=[CH2:3].CSC.B.[OH-:35].[Na+].OO>O1CCCC1>[C:13]([O:12][C:11](=[O:17])[N:10]([C:9]1[N:8]2[N:27]=[CH:28][CH:29]=[C:7]2[N:6]=[C:5]([Cl:30])[C:4]=1[CH2:1][CH2:2][CH2:3][OH:35])[C:18]1[CH:19]=[CH:20][C:21]([O:24][CH2:25][CH3:26])=[CH:22][CH:23]=1)([CH3:15])([CH3:14])[CH3:16]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 12423031(Dimethyl sulfide)trihydroboronHCID 57526828HCID 57526828, compound

Product 1

HCID 57526810HCID 57526810, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a tetrahydrofuran (23 mL) solution containing tert-butyl (6-allyl-5-chloropyrazolo[1,5-a]pyrimidin-7-yl)(4-ethoxyphenyl)carbamate (3.0 g, 7.0 mmol), borane-dimethyl sulfide complex (2 mol/L tetrahydrofuran solution, 5.6 mL, 23 mmol) was added over 30 min with ice-cooling. This mixture was stirred at room temperature for 2 hr and then again cooled on ice. Here, 1 mol/L aqueous sodium hydroxide (11.2 mL, 11.2 mmol) was added over 20 min, and hydrogen peroxide (30% aqueous solution, 0.81 mL, 8.4 mmol) was added. The resultant mixture was stirred for 1 hr. After the reaction, the reaction mixture was extracted with ethyl acetate. The combined ethyl acetate layer was washed with 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 (2.02 g, yield 65%).

Workup

  1. additionwas added over 30 min with ice-
  2. temperaturecooling
  3. temperatureagain cooled on ice
  4. customAfter the reaction
  5. extractionthe reaction mixture was extracted with ethyl acetate
  6. washThe combined ethyl acetate layer was washed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationAfter the sodium sulfate was filtered off
  9. distillationthe solvent was distilled off
  10. customthe residue was purified with column chromatography (20% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-0f0cc1a3bfc1400caa12018e093465b0
Source dataset
uspto-grants-2009_01
Patent number
US07473694B2

Reaction notes

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