Ammonium formate → HCID 135841424, compound

HRID 897502Notes

Reaction equation

HRID 897502 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:23]3[C:18](=[N:19][CH:20]=[N:21][C:22]=3[NH2:24])[N:17]([CH:25]3[CH2:29][CH2:28][CH2:27][CH2:26]3)[N:16]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1.C([O-])=O.[NH4+]>C(O)C.[Pd]>[NH2:24][C:22]1[N:21]=[CH:20][N:19]=[C:18]2[N:17]([CH:25]3[CH2:29][CH2:28][CH2:27][CH2:26]3)[N:16]=[C:15]([C:12]3[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][CH:13]=3)[C:23]=12

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 22346722HCID 22346722, compound

Product 1

HCID 135841424HCID 135841424, compoundYield 99.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-[4-(benzyloxy)phenyl]-1-cyclopentyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine (2.47 g, 6.41 mmol, 1 equiv), Pd black (0.341 g, 3.20 mmol, 0.5 equiv), and ammonium formate (2.02 g, 32 mmol, 5 equiv) in ethanol (50 mL) was heated at 80° C. for 4 h. The reaction mixture was allowed to cool to ambient temperature and the resulting solids were removed by filtration through a pad of Celite with the aid of EtOH (300 mL). The filtrate was concentrated to give a pale yellow solid which was purified by washing with CH2Cl2 (200 mL) to afford 4-(4-amino-1-cyclopentyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl)phenol as a white solid (1.89 g, 6.4 mmol): 1H NMR (d6 DMSO, 400 MHz): δH 8.22 (1H, s), 7.45 (2H, d, J=8.5 Hz), 6.92 (2H, d, J=8.5 Hz), 5.17-5.24 (1H, m), 2.01-2.10 (4H, m), 1.87-1.90 (2H, m), 1.67-1.70 (2H, m). RP-HPLC (Delta Pak C18, 5 μm, 300 Å, 15 cm; 5%-85% acetonitrile-0.1M ammonium acetate over 20 min, 1 mL/min) Rt 13.13 min. MS: MH+ 296.

Workup

  1. temperatureto cool to ambient temperature
  2. customthe resulting solids were removed by filtration through a pad of Celite with the aid of EtOH (300 mL)
  3. concentrationThe filtrate was concentrated
  4. customto give a pale yellow solid which
  5. customwas purified
  6. washby washing with CH2Cl2 (200 mL)

Sources & evidence

ORD record
ord-b7bd6034b30e4eb2a5f93d90bcbbee67
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

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