6-Chloro-m-anisidine → 4-(2-Chloro-5-methoxyanilino)-2-(4-pyridinyl)-6-(trifluoromethyl)pyrimidine

HRID 2084108Notes

Reaction equation

HRID 2084108 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.[Cl:18][C:19]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][C:20]=1[NH2:21]>>[Cl:18][C:19]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][C:20]=1[NH:21][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 754606-Chloro-m-anisidineHCID 14859894-Chloro-2-(pyridin-4-yl)-6-(trifluoromethyl)pyrimidine

Product 1

HCID 101103454-(2-Chloro-5-methoxyanilino)-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 2-chloro-5-methoxyaniline (38 mg, 0.193 mmol) similar to Example 13 and isolated as a pink solid (18 mg, 25%). 1H NMR (CDCl3): 8.82 (dd, J=1.4, 4.7 Hz, 2H), 8.32 (dd, J=1.7, 4.4 Hz, 2H), 7.84 (d, J=2.1 Hz, 1H), 7.50 (s, 1H), 7.41 (d, J=8.7 Hz, 1H), 7.02 (s, 1H), 6.77 (dd, J=3.3, 9.3 Hz, 1H), 3.90 (s, 3H).

Sources & evidence

ORD record
ord-3d5b68cb9ad541bc894197da200e7bb7
Source dataset
uspto-grants-2004_04
Patent number
US06716851B2

Reaction notes

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