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

HRID 1786721Notes

Reaction equation

HRID 1786721 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[CH:5]=[CH:4][N:3]=1.[NH2:14][C:15]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[CH:17][C:16]=1[CH3:24].[OH-].[Na+]>Cl.C(O)CCC>[CH3:24][C:16]1[CH:17]=[CH:18][C:19]([N+:21]([O-:23])=[O:22])=[CH:20][C:15]=1[NH:14][C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 74442-Methyl-5-NitroanilineHCID 14798Sodium HydroxideHCID 118055432-Chloro-4-(pyridin-3-yl)pyrimidine

Product 1

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

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 2631-ButanolSolvent

Procedure

A 250 ml reactor, equipped with a mechanical stirrer and a reflux condenser, was charged with 2-chloro-4-(3-pyridyl)-pyrimidine (0.5 g, 2.6 mmol), 2-amino-4-nitrotoluene (0.5 g, 3.2 mmol), n-butanol (15 ml) and concentrated HCl (5 drops) and the mixture was refluxed for 38 hours. Then, the mixture was cooled, and 6 N NaOH was added to pH 8. The solvent was evaporated under reduced pressure and water (20 ml) was added to the residue, followed by extraction with dichloromethane (2×20 ml). The combined organic phase was concentrated to dryness to give the crude N-(2-methyl-5-nitrophenyl)-4-(3-pyridyl)-pyrimidine-amine, which was purified by column chromatography to yield a product having 80% purity. The residue was re-slurried twice in methanol (2×2 ml) and in water (3 ml) and dried under reduced pressure.

Workup

  1. customA 250 ml reactor, equipped with a mechanical stirrer and a reflux condenser
  2. temperaturethe mixture was refluxed for 38 hours
  3. temperatureThen, the mixture was cooled
  4. customThe solvent was evaporated under reduced pressure and water (20 ml)
  5. additionwas added to the residue
  6. extractionfollowed by extraction with dichloromethane (2×20 ml)
  7. concentrationThe combined organic phase was concentrated to dryness

Sources & evidence

ORD record
ord-87bb5e01cf2e42c38248e11b31a483e7
Source dataset
uspto-grants-2009_03
Patent number
US07507821B2

Reaction notes

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