[1-(6-Amino-pyrimidin-4-yl)-1H-benzoimidazol-2-yl]-(2-methyl-5-nitro-phenyl)-amine → N3-[1-(6-Amino-pyrimidin-4-yl)-1H-benzoimidazol-2-yl]-4-methyl-benzene-1,3-diamine

HRID 1968424

Reaction equation

HRID 1968424 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([N:8]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[N:10]=[C:9]2[NH:17][C:18]2[CH:23]=[C:22]([N+:24]([O-])=O)[CH:21]=[CH:20][C:19]=2[CH3:27])[CH:3]=1>C(O)C.[Pd]>[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([N:8]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[N:10]=[C:9]2[NH:17][C:18]2[CH:23]=[C:22]([NH2:24])[CH:21]=[CH:20][C:19]=2[CH3:27])[CH:3]=1

Participants

4

Reactant 1

HCID 15949047[1-(6-Amino-pyrimidin-4-yl)-1H-benzoimidazol-2-yl]-(2-methyl-5-nitro-phenyl)-amine

Product 1

HCID 15948950N3-[1-(6-Amino-pyrimidin-4-yl)-1H-benzoimidazol-2-yl]-4-methyl-benzene-1,3-diamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

[1-(6-Amino-pyrimidin-4-yl)-1H-benzoimidazol-2-yl]-(2-methyl-5-nitrophenyl)-amine (135 mg, 0.37 mmol) is dissolved in ethanol (30 mL). After hydrogenation catalyzed by palladium (10 wt % on activated carbon, wet, Degussa type, 22 mg) under 1 atm H2 balloon overnight, the reaction mixture is filtered through a pad of celite and washed with ethanol. The combined filtrate and washings are concentrated to afford the title compound, which is used for next reaction without any further purification.

Workup

  1. filtrationthe reaction mixture is filtered through a pad of celite
  2. washwashed with ethanol
  3. concentrationThe combined filtrate and washings are concentrated

Sources & evidence

ORD record
ord-df738a17d522404a9b50ca0761e77f2b
Source dataset
uspto-grants-2013_04
Patent number
US08426404B2

Linked notes

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