N-(4-methyl-3-nitrophenyl)-4-(3-pyridyl)-2-pyrimidine-amine → N-(3-amino-4-methylphenyl)-4-(pyridin-3-yl)-2-pyrimidine-amine

HRID 736300Notes

Reaction equation

HRID 736300 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:14]=[C:13]([C:15]3[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=3)[CH:12]=[CH:11][N:10]=2)=[CH:4][C:3]=1[N+:21]([O-])=O>C(OCC)(=O)C.C(O)C>[NH2:21][C:3]1[CH:4]=[C:5]([NH:8][C:9]2[N:14]=[C:13]([C:15]3[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=3)[CH:12]=[CH:11][N:10]=2)[CH:6]=[CH:7][C:2]=1[CH3:1]

Participants

4

Reactant 1

HCID 68816439N-(4-methyl-3-nitrophenyl)-4-(3-pyridyl)-2-pyrimidine-amine

Product 1

HCID 24820369N-(3-amino-4-methylphenyl)-4-(pyridin-3-yl)-2-pyrimidine-amineYield 104.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-(4-methyl-3-nitrophenyl)-4-(3-pyridyl)-2-pyrimidine-amine (34 g, 0.11 mol) and stannous chloride dihydrate (124.5 g, 0.55 mol) were dissolved in a solvent mixture of ethyl acetate and ethanol (300 ml, 10/1, v/v) and reacted under reflux for 26 hours. The reaction mixture was cooled to room temperature, washed with 10% aqueous hydrochloric acid solution, concentrated, and subjected to column chromatography (chloroform/methanol=9/1, v/v) to give N-(3-amino-4-methylphenyl)-4-(3-pyridyl)-2-pyrimidine-amine (32 g).

Workup

  1. customv/v) and reacted
  2. temperatureunder reflux for 26 hours
  3. washwashed with 10% aqueous hydrochloric acid solution
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-015014954fee462796a60df3b49d6c6c
Source dataset
uspto-grants-2009_09
Patent number
US07595323B2

Reaction notes

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