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

HRID 2084144Notes

Reaction equation

HRID 2084144 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][N: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][CH:15]=[CH:14][N:13]=2)[N:3]=1

Participants

3

Reactant 2

HCID 754606-Chloro-m-anisidineHCID 113115004-Chloro-2-(2-pyridinyl)-6-(trifluoromethyl)pyrimidine

Product 1

HCID 227323704-(2-Chloro-5-methoxyanilino)-2-(2-pyridinyl)-6-(trifluoromethyl)pyrimidine

Procedure

The title compound was prepared from a mixture of 4-chloro-2-(2-pyridinyl)-6-(trifluoromethyl)pyrimidine (25 mg, 0.096 mmol) and 2-chloro-5-methoxyaniline (23 mg, 0.144 mmol) similar to Example 92 and isolated as a white solid (11 mg, 48%). 1H NMR (CDCl3): 8.84-8.82 (m, 1H), 8.58-8.54 (m, 1H), 7.90-7.85 (m, 1H), 7.66 (s, 1H), 7.60 (s, 1H), 7.46-7.41 (m, 1H), 7.37 (d, J=8.7 Hz, 1H), 7.01 (s, 1H), 6.75 (dd, J=3.0, 8.7 Hz, 1H), 3.88 (s, 3H).

Sources & evidence

ORD record
ord-0a47a93a7b094eecb6ba5e5f8a38a723
Source dataset
uspto-grants-2004_04
Patent number
US06716851B2

Reaction notes

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