Triphenylphosphine → HCID 86721084, compound

HRID 923303Notes

Reaction equation

HRID 923303 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[NH:8][N:9]=[CH:10][C:3]=12.[N:11]1([CH2:17][CH2:18]O)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH2:18][CH2:17][N:11]3[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]3)[N:9]=[CH:10][C:3]=12

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 18232N-PiperidinoethanolHCID 2210954-Chloro-1H-pyrazolo[3,4-d]pyrimidineHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 86721084HCID 86721084, compoundYield 4,263.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 4-chloro-1H-pyrazolo[3,4-d]pyrimidine (0.2 g, 1.29 mmol) in anh THF (10 mL), 2-(piperidin-1-yl)ethanol (0.258 mL, 1.94 mmol) and triphenylphosphine (0.51 g, 1.94 mmol) were sequentially added. The reaction mixture was cooled to 0° C. and diisopropylazodicarboxylate (0.38 mL, 1.94 mmol) was added dropwise. The mixture was stirred for 30 min. at 0° C. and kept overnight at 4° C. The solvent was removed at reduced pressure and the residue was dissolved in DCM and washed with diluted HCl 1N. The aqueous phase was separated, basified and extracted with DCM. The organic phase was separated, dried and the solvent was removed under reduced pressure to give a residue that was purified by flash chromatography eluting with (EtOAc/Petroleum ether, 8:2) to yield 4-chloro-1-(2-(piperidin-1-yl)ethyl)-1H-pyrazolo[3,4-d]pyrimidine (146 mg, 55 mmol, 42%) as an oil that solidifies “on standing”.

Workup

  1. waitkept overnight at 4° C
  2. customThe solvent was removed at reduced pressure
  3. dissolutionthe residue was dissolved in DCM
  4. washwashed with diluted HCl 1N
  5. customThe aqueous phase was separated
  6. extractionextracted with DCM
  7. customThe organic phase was separated
  8. customdried
  9. customthe solvent was removed under reduced pressure
  10. customto give a residue that
  11. customwas purified by flash chromatography
  12. washeluting with (EtOAc/Petroleum ether, 8:2)

Sources & evidence

ORD record
ord-ce318b19611c4b648188d0064275d06b
Source dataset
uspto-grants-2016_03
Patent number
US09278974B2

Reaction notes

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