Sodium Hydroxide → 4-(3-Phenylanilino)-2-(3-pyridinyl)-6-(trifluoromethyl)pyrimidine

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.[NH2:18][C:19]1[CH:20]=[C:21]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:22]=[CH:23][CH:24]=1.[OH-].[Na+]>>[C:25]1([C:21]2[CH:20]=[C:19]([CH:24]=[CH:23][CH:22]=2)[NH:18][C:2]2[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[N:5]=[C:4]([C:12]3[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=3)[N:3]=2)[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

Reactant 3

HCID 14798Sodium Hydroxide

HCID 167173-Aminobiphenyl

HCID 14859904-Chloro-2-(pyridin-3-yl)-6-(trifluoromethyl)pyrimidine

Product 1

HCID 227323724-(3-Phenylanilino)-2-(3-pyridinyl)-6-(trifluoromethyl)pyrimidine

Procedure

The title compound was prepared from a mixture of 4-chloro-2-(3-pyridinyl)-6-(trifluoromethyl)pyrimidine (50 mg, 0.193 mmol) and 3-aminobiphenyl (65 mg, 0.386 mmol) similar to Example 58. The mixture was basified with aqueous 2N NaOH to pH 10–12. The resulting precipitate was collected by filtration, washed with excess water:ethanol (1:1) and isolated as a light brown solid (64 mg, 85%). 1H NMR (CDCl3): 9.67 (s, 1H), 8.75 (d, J=5.4 Hz, 2H), 7.68 (s, 1H), 7.63–7.37 (m, 10H), 6.98 (s, 1H).