Ethylamine → tert-butyl 4-((6-(methylamino)-3-phenyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)cyclohexylcarbamate

HRID 928237Notes

Reaction equation

HRID 928237 reaction equation
[C:1]([O:5][C:6](=[O:32])[NH:7][CH:8]1[CH2:13][CH2:12][CH:11]([CH2:14][N:15]2[C:19]3=[N:20][C:21](SC)=[N:22][CH:23]=[C:18]3[C:17]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[N:16]2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].ClC1C=C(C=CC=1)C(OO)=O.[CH2:44]([NH2:46])C>C(Cl)Cl>[CH3:44][NH:46][C:21]1[N:20]=[C:19]2[N:15]([CH2:14][CH:11]3[CH2:12][CH2:13][CH:8]([NH:7][C:6](=[O:32])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:9][CH2:10]3)[N:16]=[C:17]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:18]2=[CH:23][N:22]=1

Participants

5

Reactant 3

HCID 6341EthylamineHCID 70297m-Chloroperbenzoic acidHCID 67470951tert-Butyl-4-((6-(methylthio)-3-phenyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)cyclohexylcarbamate

Product 1

HCID 68212392tert-butyl 4-((6-(methylamino)-3-phenyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)cyclohexylcarbamateYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-Butyl-4-((6-(methylthio)-3-phenyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)cyclohexylcarbamate (0.14 g, 0.3 mmol) in methylene chloride (5 mL) was added meta-chloroperoxybenzoic acid (0.20 g, 0.9 mmol) at room temperature. After stirring at room temperature for 2 h, the light purple solution was quenched with a 1.0 N aqueous solution of NaOH. The aqueous layer was extracted with EtOAc (3×). The organic layers were combined, dried (Na2SO4), and concentrated. The residue was dissolved in THF (1 mL), followed by the addition of ethylamine (1.5 mL, 2.0 M in THF, 3 mmol). The resulting solution was heated at 60° C. for 2 h, cooled to room temperature, and concentrated. The crude mixture was purified by Isco to provide tert-butyl 4-((6-(methylamino)-3-phenyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)cyclohexylcarbamate (0.085 g, 81%) as a white solid.

Workup

  1. customthe light purple solution was quenched with a 1.0 N aqueous solution of NaOH
  2. extractionThe aqueous layer was extracted with EtOAc (3×)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in THF (1 mL)
  6. temperatureThe resulting solution was heated at 60° C. for 2 h
  7. temperaturecooled to room temperature
  8. concentrationconcentrated
  9. customThe crude mixture was purified by Isco

Sources & evidence

ORD record
ord-cd03b1c0bd6d4da88545609bc0d73014
Source dataset
uspto-grants-2016_03
Patent number
US09290499B2

Reaction notes

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