Ammonium formate → 1-(2-Fluorobenzyl)-3-[5-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)-2-pyrimidinyl]-1H-pyrazolo[3,4-b]pyridine

HRID 8587Notes

Reaction equation

HRID 8587 reaction equation
Cl[C:2]1[C:7]([N:8]2[CH2:14][CH:13]3[O:15][CH:10]([CH2:11][CH2:12]3)[CH2:9]2)=[C:6](Cl)[N:5]=[C:4]([C:17]2[C:25]3[C:20](=[N:21][CH:22]=[CH:23][CH:24]=3)[N:19]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[F:33])[N:18]=2)[N:3]=1.C([O-])=O.[NH4+]>CO.[Pd]>[F:33][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[CH2:26][N:19]1[C:20]2=[N:21][CH:22]=[CH:23][CH:24]=[C:25]2[C:17]([C:4]2[N:5]=[CH:6][C:7]([N:8]3[CH2:9][CH:10]4[O:15][CH:13]([CH2:12][CH2:11]4)[CH2:14]3)=[CH:2][N:3]=2)=[N:18]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 219835303-[4,6-Dichloro-5-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)-2-pyrimidinyl]-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine

Product 1

HCID 219835371-(2-Fluorobenzyl)-3-[5-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)-2-pyrimidinyl]-1H-pyrazolo[3,4-b]pyridine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

400 mg (0.68 mmol) of 3-[4,6-dichloro-5-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)-2-pyrimidinyl]-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine (example XII, step 7) are dissolved in 200 ml of methanol, and 86 mg of ammonium formate are added. Under argon, 26 mg of palladium on activated carbon (10%) are added, and the mixture is heated under reflux for 3 days. The reaction mixture is filtered and the residues are washed with methanol. The solvent is removed in vacuo, and the residue is purified by preparative HPLC. 99 mg (35% of theory) of the product are obtained.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 3 days
  3. filtrationThe reaction mixture is filtered
  4. washthe residues are washed with methanol
  5. customThe solvent is removed in vacuo
  6. customthe residue is purified by preparative HPLC
  7. custom99 mg (35% of theory) of the product are obtained

Sources & evidence

ORD record
ord-95a3c85d0be542beac729e463c062d1c
Source dataset
uspto-grants-2006_08
Patent number
US07091198B1

Reaction notes

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