Benzyl Bromide → 3-(4,6-Diamino-5-benzylpyrimidin-2-yl)-1-(2-fluorobenzyl)-1h-pyrazolo[3,4-b]pyridine

HRID 351661Notes

Reaction equation

HRID 351661 reaction equation
[F:1][C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[C:7]([C:14]([NH2:16])=[NH:15])=[N:6]1.[CH2:21]([C:24]#[N:25])[C:22]#[N:23].[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(=O)([O-])[O-].[K+].[K+].N1CCCCC1>CC(O)CCC>[NH2:23][C:22]1[C:21]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[C:24]([NH2:25])[N:16]=[C:14]([C:7]2[C:8]3[C:9](=[N:10][CH:11]=[CH:12][CH:13]=3)[N:5]([CH2:4][C:3]3[CH:17]=[CH:18][CH:19]=[CH:20][C:2]=3[F:1])[N:6]=2)[N:15]=1

Participants

7

Reactant 5

HCID 7498Benzyl BromideHCID 8010MalononitrileHCID 8082PiperidineHCID 11430Potassium CarbonateHCID 114039861-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carboximidamide

Product 1

HCID 99321903-(4,6-Diamino-5-benzylpyrimidin-2-yl)-1-(2-fluorobenzyl)-1h-pyrazolo[3,4-b]pyridine

Reagents, catalysts & solvents 1

HCID 223862-PentanolSolvent

Procedure

At 110° C., 200 mg (0.74 mmol) of 1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carboxamidine from Example 25A, 125 mg (0.8 mmol) of 2-benzylmalonodinitrile (preparable from malonodinitrile and benzyl bromide using a base such as potassium carbonate), 0.68 mg (0.8 mmol) of piperidine and 20 ml of 2-pentanol are stirred for 12 h. After cooling, the solvent is evaporated under reduced pressure and the residue is chromatographed over silica gel. This gives 165 mg (52.2% of theory) of the title compound.

Workup

  1. temperatureAfter cooling
  2. customthe solvent is evaporated under reduced pressure
  3. customthe residue is chromatographed over silica gel

Sources & evidence

ORD record
ord-035ab1d32ff540cbb8e18a54860f572a
Source dataset
uspto-grants-2004_06
Patent number
US06743798B1

Reaction notes

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