Hydrochloric Acid → 4-(2-Methyl-5-nitroanilino)-2-(3-pyridinyl)-6-(trifluoromethyl)pyrimidine

HRID 1765193Notes

Reaction equation

HRID 1765193 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[N:5]=[C:4]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[N:3]=1.[CH3:18][C:19]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][C:20]=1[NH2:21].Cl.[OH-].[Na+]>O.C(O)C>[CH3:18][C:19]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][C:20]=1[NH:21][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[N:5]=[C:4]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[N:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 74442-Methyl-5-NitroanilineHCID 14798Sodium HydroxideHCID 14859904-Chloro-2-(pyridin-3-yl)-6-(trifluoromethyl)pyrimidine

Product 1

HCID 99696934-(2-Methyl-5-nitroanilino)-2-(3-pyridinyl)-6-(trifluoromethyl)pyrimidineYield 19%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

A mixture of 4-chloro-2-(3-pyridinyl)-6-(trifluoromethyl)pyrimidine (500 mg, 1.93 mmol), 2-methyl,5-nitroaniline (441 mg, 2.90 mmol), and 2N HCl (1.5 ml) in water:ethanol (1:1, 100 ml) was refluxed for 48 h. The mixture was cooled to room temperature and basified with aqueous 2N NaOH to pH 10–12. The resulting precipitate was filtered, washed with water and water:ethanol (2:1). The product was dried under vacuo and then washed with chloroform to give a yellow solid (136 mg, 19%). 1H NMR (DMSO-d6): 9.84 (s, 1H), 9.41 (s, 1H), 8.99 (s, 1H), 8.73 (d, J=4.2 Hz, 1H), 8.57 (d, J=7.8 Hz, 1H), 8.02 (dd, J=1.8, 7.8, 1H), 7.61 (d, J=8.1 Hz, 1H), 7.58–7.54 (m, 1H), 7.39 (s, 1H), 2.45 (s, 3H).

Workup

  1. temperaturewas refluxed for 48 h
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with water and water:ethanol (2:1)
  4. customThe product was dried under vacuo
  5. washwashed with chloroform

Sources & evidence

ORD record
ord-bb07be87c11f4447be6826fae4083cca
Source dataset
uspto-grants-2007_06
Patent number
US07226927B2

Reaction notes

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