Sodium Hydroxide → 2-(2-Methyl-5-nitroanilino)-4-(3-pyridyl)pyrimidine

HRID 1766989Notes

Reaction equation

HRID 1766989 reaction equation
[N+]([O-])(O)=O.[CH3:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:7]=1[NH:15][C:16]([NH2:18])=[NH:17].CN(C)[CH:21]=[CH:22][C:23]([C:25]1[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=1)=O.[OH-].[Na+]>C(O)(C)C>[CH3:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:7]=1[NH:15][C:16]1[N:18]=[C:23]([C:25]2[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=2)[CH:22]=[CH:21][N:17]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 5670331-(3-Pyridyl)-3-(dimethylamino)-2-propen-1-oneHCID 178426711HCID 178426711, compound

Product 1

HCID 106861492-(2-Methyl-5-nitroanilino)-4-(3-pyridyl)pyrimidine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 2-methyl-5-nitrophenylguanidine nitrate (25 g, 96 mmol) and 3-dimethylamino-1-(3-pyridyl)-2-propen-1-one (17 g, 96 mmol) in isopropanol (200 ml) was added sodium hydroxide (4.5 g). The reaction was refluxed for 12 hours and cooled to 0° C. The precipitate was filtered and washed with isopropanol to give N-(2-methyl-5-nitrophenyl)-4-(3-pyridyl)-2-pyrimidine-amine.

Workup

  1. temperatureThe reaction was refluxed for 12 hours
  2. filtrationThe precipitate was filtered
  3. washwashed with isopropanol

Sources & evidence

ORD record
ord-f580364c29f64504950f13b31a84730c
Source dataset
uspto-grants-2007_06
Patent number
US07232825B2

Reaction notes

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