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

HRID 440869

Reaction equation

HRID 440869 reaction equation
[N+]([O-])(O)=O.[N+:5]([C:8]1[CH:9]=[C:10]([NH:14][C:15]([NH2:17])=[NH:16])[CH:11]=[CH:12][CH:13]=1)([O-:7])=[O:6].[OH-].[Na+].CN(C)[CH:22]=[CH:23][C:24]([C:26]1[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=1)=O>C(O)(C)C>[N+:5]([C:8]1[CH:9]=[C:10]([NH:14][C:15]2[N:17]=[C:24]([C:26]3[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=3)[CH:23]=[CH:22][N:16]=2)[CH:11]=[CH:12][CH:13]=1)([O-:7])=[O:6]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 7145312-Propen-1-one, 3-(dimethylamino)-1-(4-pyridinyl)-HCID 1785125133-Nitrophenylguanidine Nitrate

Product 1

HCID 9814609N-(3-nitrophenyl)-4-(4-pyridyl)-2-pyrimidine-amine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

1.38 g (5.68 mmol) of 3-nitrophenyl-guanidine nitrate and 0.25 g (6.24 mmol) of sodium hydroxide are added to a solution of 1 g (5.68 mmol) of 3-dimethylamino-1-(4-pyridyl)-2-propen-1-one [U.S. Pat. No. 4,281,000] in 8 ml of isopropanol. The yellow suspension is heated at reflux for 20 hours and then cooled to 0°. After washing with 30 ml of isopropanol the filtration residue is made into a slurry in succession in 15 ml of ethanol and then in 15 ml of water and filtered each time. Drying under HV yields N-(3-nitrophenyl)-4-(4-pyridyl)-2-pyrimidine-amine; m.p. 282°-284°.

Workup

  1. temperatureThe yellow suspension is heated
  2. temperatureat reflux for 20 hours
  3. temperaturecooled to 0°
  4. washAfter washing with 30 ml of isopropanol the filtration residue
  5. filtrationin 15 ml of water and filtered each time
  6. customDrying under HV

Sources & evidence

ORD record
ord-e3808de72dab45edb0e711b8bcc44ce3
Source dataset
uspto-grants-1996_05
Patent number
US05521184

Linked notes

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