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

HRID 2084131Notes

Reaction equation

HRID 2084131 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-0a3e6297671f460b8f089111eb8e54ee
Source dataset
uspto-grants-2004_04
Patent number
US06716851B2

Reaction notes

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