Sodium Hydroxide → 4-(2-Chloro-5-methoxyanilino)-2-phenyl-6-(trifluoromethyl)pyrimidine

HRID 1765185Notes

Reaction equation

HRID 1765185 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:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:3]=1.Cl.[Cl:19][C:20]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][C:21]=1[NH2:22].[OH-].[Na+]>O.C(O)C>[Cl:19][C:20]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][C:21]=1[NH:22][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[N:5]=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 6141014-Chloro-2-phenyl-6-(trifluoromethyl)pyrimidineHCID 27239002-Chloro-5-methoxyanilinium chloride

Product 1

HCID 227325094-(2-Chloro-5-methoxyanilino)-2-phenyl-6-(trifluoromethyl)pyrimidineYield 38.2%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

A mixture of 4-chloro-2-phenyl-6-(trifluoromethyl)pyrimidine (50 mg, 0.193 mmol) and 2-chloro-5-methoxyaniline hydrochloride (56 mg, 0.290 mmol) in water:ethanol (1:1, 10 ml) was refluxed for 48 h. The mixture was cooled to room temperature and then basified with aqueous 2N NaOH to pH 10–12. The resulting precipitate was filtered, washed with water, water:ethanol (2:1) and isolated as a brown solid (28 mg, 38%). 1H NMR (CDCl3): 8.50–8.47 (m, 2H), 7.99 (d, J=3.0 Hz, 1H), 7.53–7.47 (m, 3H), 7.36 (d, J=9.0 Hz, 1H), 7.29 (s, 1H), 6.91 (s, 1H), 6.71 (dd, J=3.0, 9.0 Hz, 1H), 3.88 (s, 3H).

Workup

  1. temperaturewas refluxed for 48 h
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with water, water:ethanol (2:1)

Sources & evidence

ORD record
ord-47e50ca6067747e3aa00ddb6d12238e1
Source dataset
uspto-grants-2007_06
Patent number
US07226927B2

Reaction notes

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