2,5-Dimethoxyaniline → 4-(2,5-Dimethoxyanilino)-2-(3-pyridinyl)-6-(trifluoromethyl)pyrimidine

HRID 2084095

Reaction equation

HRID 2084095 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][O:19][C:20]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][C:21]=1[NH2:22]>>[CH3:18][O: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:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[N:3]=1

Participants

3

Reactant 2

HCID 76132,5-DimethoxyanilineHCID 14859904-Chloro-2-(pyridin-3-yl)-6-(trifluoromethyl)pyrimidine

Product 1

HCID 101563584-(2,5-Dimethoxyanilino)-2-(3-pyridinyl)-6-(trifluoromethyl)pyrimidine

Procedure

The title compound was prepared from a mixture of 4-chloro-2-(3-pyridinyl)-6-(trifluoromethyl)pyrimidine (100 mg, 0.385 mmol) and 2,5-dimethoxyaniline (59 mg, 0.385 mmol) similar to Example 13 and isolated as a greenish-yellow solid (24 mg, 17%). 1H NMR (CDCl3): 9.67-9.66 (m, 1H), 8.74-8.70 (m, 2H), 8.02 (s, 1H), 7.44-7.39 (m, 1H), 6.91 (s, 1H), 7.67 (s, 1H), 6.87 (d, J=8.7 Hz, 1H), 6.65 (dd, J=3.0, 9.0 Hz, 1H), 3.86 (d, J=7.2 Hz, 6H).

Sources & evidence

ORD record
ord-95b7d0432a854a9fbd794c50ba69eb36
Source dataset
uspto-grants-2004_04
Patent number
US06716851B2

Linked notes

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