Ammonium formate → 4-(5-amino-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-(isopropylamino)pyrimidine-5-carbonitrile

HRID 887366Notes

Reaction equation

HRID 887366 reaction equation
[C:1]([C:3]1[C:4]([C:13]2[C:21]3[C:16](=[N:17][CH:18]=[C:19]([NH:22]C(=O)OCC4C=CC=CC=4)[CH:20]=3)[N:15]([S:33]([C:36]3[CH:42]=[CH:41][C:39]([CH3:40])=[CH:38][CH:37]=3)(=[O:35])=[O:34])[CH:14]=2)=[N:5][C:6]([NH:9][CH:10]([CH3:12])[CH3:11])=[N:7][CH:8]=1)#[N:2].C([O-])=O.[NH4+]>CCO.[Pd]>[NH2:22][C:19]1[CH:20]=[C:21]2[C:13]([C:4]3[C:3]([C:1]#[N:2])=[CH:8][N:7]=[C:6]([NH:9][CH:10]([CH3:11])[CH3:12])[N:5]=3)=[CH:14][N:15]([S:33]([C:36]3[CH:37]=[CH:38][C:39]([CH3:40])=[CH:41][CH:42]=3)(=[O:34])=[O:35])[C:16]2=[N:17][CH:18]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 68668357Benzyl 3-(5-cyano-2-(isopropylamino)pyrimidin-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-ylcarbamate

Product 1

HCID 686682684-(5-amino-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-(isopropylamino)pyrimidine-5-carbonitrile

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Benzyl 3-(5-cyano-2-(isopropylamino)pyrimidin-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-ylcarbamate (0.199 g, 0.342 mmol) in EtOH (15 mL) was charged with ammonium formate (0.129 g, 2.055 mmol, 6.0 Eq) and 10% Pd/C (0.040 g, 0.2 Eq) and heated at reflux for 3 hours.

Workup

  1. temperatureheated
  2. temperatureat reflux for 3 hours

Sources & evidence

ORD record
ord-27f1bdfd7d10483080f5c0d9e3c94abe
Source dataset
uspto-grants-2012_08
Patent number
US08247421B2

Reaction notes

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