HCID 11281976, compound → HCID 21897527, compound

HRID 1864152Notes

Reaction equation

HRID 1864152 reaction equation
C([N:8]1[CH2:11][CH:10]([O:12][C:13]2[N:18]=[CH:17][N:16]=[C:15]3[N:19]([C:22]4[CH:27]=[CH:26][C:25]([S:28]([CH3:31])(=[O:30])=[O:29])=[CH:24][CH:23]=4)[N:20]=[CH:21][C:14]=23)[CH2:9]1)C1C=CC=CC=1.[H][H]>C(OCC)(=O)C.CO.[Pd]>[NH:8]1[CH2:9][CH:10]([O:12][C:13]2[N:18]=[CH:17][N:16]=[C:15]3[N:19]([C:22]4[CH:23]=[CH:24][C:25]([S:28]([CH3:31])(=[O:30])=[O:29])=[CH:26][CH:27]=4)[N:20]=[CH:21][C:14]=23)[CH2:11]1

Participants

6

Reactant 2

HCID 11281976HCID 11281976, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21897527HCID 21897527, compoundYield 318.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-(1-Benzyl-azetidin-3-yloxy)-1-(4-methanesulfonyl-phenyl)-1H-pyrazolo[3,4-d]pyrimidine (0.01 mmol, 46 mg) was dissolved in a mixture of ethyl acetate (5 mL) and methanol (5 mL). Palladium catalyst (30 mg, 65% by wt) was added to the reaction. The mixture was exposed to hydrogen gas for 60. minutes at room temperature and atmospheric pressure. The mixture was passed through celite to remove palladium catalyst. Removal of organic solvents in vacuo and purification by flash chromatography provided 4-(azetidin-3-yloxy)-1-(4-methanesulfonyl-phenyl)-1H-pyrazolo[3,4-d]pyrimidine as a white solid (11 mg, 5%). 1H NMR (400MHz, MeOH-d4) δ (ppm): 8.45 (m, 2H); 8.37 (d, 2H); 8.05 (d, 2H); 4.54 (m, 1H); 4.35 (dd, 2H); 3.69 (m, 2H); 3.09 (s, 3H). LCMS (ESI), m/z 346.2 (M+H+, 100%).

Workup

  1. customat room temperature
  2. customto remove palladium catalyst
  3. customRemoval of organic solvents
  4. customin vacuo and purification by flash chromatography

Sources & evidence

ORD record
ord-40c99b2099b047c69b54c23650c2c5f8
Source dataset
uspto-grants-2009_12
Patent number
US07625906B2

Reaction notes

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