3-cyclopropyl-3-(4-{5-methoxy-2-[(3-nitrophenyl)amino]pyrimidin-4-yl}-1H-pyrazol-1-yl)propanenitrile → 3-(4-{2-[(3-aminophenyl)amino]-5-methoxypyrimidin-4-yl}-1H-pyrazol-1-yl)-3-cyclopropylpropanenitrile

HRID 1876901Notes

Reaction equation

HRID 1876901 reaction equation
[CH:1]1([CH:4]([N:8]2[CH:12]=[C:11]([C:13]3[C:18]([O:19][CH3:20])=[CH:17][N:16]=[C:15]([NH:21][C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([N+:28]([O-])=O)[CH:23]=4)[N:14]=3)[CH:10]=[N:9]2)[CH2:5][C:6]#[N:7])[CH2:3][CH2:2]1.[H][H]>CO.[Pd]>[NH2:28][C:24]1[CH:23]=[C:22]([NH:21][C:15]2[N:14]=[C:13]([C:11]3[CH:10]=[N:9][N:8]([CH:4]([CH:1]4[CH2:3][CH2:2]4)[CH2:5][C:6]#[N:7])[CH:12]=3)[C:18]([O:19][CH3:20])=[CH:17][N:16]=2)[CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 2

HCID 580145013-cyclopropyl-3-(4-{5-methoxy-2-[(3-nitrophenyl)amino]pyrimidin-4-yl}-1H-pyrazol-1-yl)propanenitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 580145283-(4-{2-[(3-aminophenyl)amino]-5-methoxypyrimidin-4-yl}-1H-pyrazol-1-yl)-3-cyclopropylpropanenitrile

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 3-cyclopropyl-3-(4-{5-methoxy-2-[(3-nitrophenyl)amino]pyrimidin-4-yl}-1H-pyrazol-1-yl)propanenitrile (from example 321, 0.010 g, 0.000025 mol) in 2 mL of MeOH was hydrogenated in the presence of 10% Pd/C, under balloon pressure of hydrogen, for 2 h. After filtering off the catalyst, the filtrate was evaporated to dryness to provide the desired product as a racemic mixture (8 mg, 86.39%). LCMS (M+H) 376.1.

Workup

  1. filtrationAfter filtering off the catalyst
  2. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-a122926773af43de8521c74475b77b11
Source dataset
uspto-grants-2012_11
Patent number
US08309718B2

Reaction notes

Loading…