4-Amino-2,5-dimethylphenol → 4-(2,5-Dimethyl-4-hydroxyanilino)-2-(4-pyridinyl)-6-(trifluoromethyl)pyrimidine

HRID 1765245Notes

Reaction equation

HRID 1765245 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][N:15]=[CH:14][CH:13]=2)[N:3]=1.[NH2:18][C:19]1[C:24]([CH3:25])=[CH:23][C:22]([OH:26])=[C:21]([CH3:27])[CH:20]=1>>[CH3:25][C:24]1[CH:23]=[C:22]([OH:26])[C:21]([CH3:27])=[CH:20][C:19]=1[NH:18][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][N:15]=[CH:14][CH:13]=2)[N:3]=1

Participants

3

Reactant 2

HCID 765444-Amino-2,5-dimethylphenolHCID 14859894-Chloro-2-(pyridin-4-yl)-6-(trifluoromethyl)pyrimidine

Product 1

HCID 1357943474-(2,5-Dimethyl-4-hydroxyanilino)-2-(4-pyridinyl)-6-(trifluoromethyl)pyrimidine

Procedure

The title compound was prepared from a mixture of 4-chloro-2-(4-pyridinyl)-6-(trifluoromethyl)pyrimidine (50 mg, 0.193 mmol) and 4-amino-2,5-dimethylphenol (40 mg, 0.290 mmol) similar to Example 117 and isolated as a white solid (2 mg). 1H NMR (CDCl3): 8.77 (d, J=6.0 Hz, 2H), 8.27 (d, J=6.3 Hz, 2H), 7.05 (s, 1H), 6.86 (s, 1H), 6.77 (s, 1H), 6.47 (s, 1H), 5.25 (bs, 1H), 2.26 (s, 3H), 2.19 (s, 3H).

Sources & evidence

ORD record
ord-a0e0e7561106432391834bc771bfe730
Source dataset
uspto-grants-2007_06
Patent number
US07226927B2

Reaction notes

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