Sodium Hydroxide → N-(4-methyl-3-nitrophenyl)-4-(3-pyridyl)-2-pyrimidine-amine

HRID 736302Notes

Reaction equation

HRID 736302 reaction equation
CN(C)[CH:3]=[CH:4][C:5]([C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1)=O.[N+]([O-])(O)=O.[CH3:18][C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26]([NH2:28])=[NH:27])=[CH:21][C:20]=1[N+:29]([O-:31])=[O:30].[OH-].[Na+]>C(O)(C)C>[CH3:18][C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26]2[N:28]=[C:5]([C:7]3[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=3)[CH:4]=[CH:3][N:27]=2)=[CH:21][C:20]=1[N+:29]([O-:31])=[O:30]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 5670331-(3-Pyridyl)-3-(dimethylamino)-2-propen-1-oneHCID 178426527HCID 178426527, compound

Product 1

HCID 68816439N-(4-methyl-3-nitrophenyl)-4-(3-pyridyl)-2-pyrimidine-amineYield 104,130,488%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
0 °C

Procedure

3-Dimethylamino-1-(3-pyridyl)-2-propen-1-one (20 g, 0.1 μmol), 4-methyl-3-nitrophenyl-guanidine nitrate (32 g, 0.12 mol), and sodium hydroxide (6.8 g, 0.17 mol) were dissolved in isopropanol, and reacted under reflux for 28 hours. The reaction solution was cooled to 0° C., filtered, washed with isopropanol, water and ethanol, and dried to give N-(4-methyl-3-nitrophenyl)-4-(3-pyridyl)-2-pyrimidine-amine (32 g).

Workup

  1. customreacted
  2. temperatureunder reflux for 28 hours
  3. filtrationfiltered
  4. washwashed with isopropanol, water and ethanol
  5. customdried

Sources & evidence

ORD record
ord-c889cb5cf0f146dbb3fcec9eacea389b
Source dataset
uspto-grants-2009_09
Patent number
US07595323B2

Reaction notes

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