4-Chloro-5-methyl-o-anisidine → 4-(4-Chloro-2-methoxy-5-methylanilino)-2-(3-pyridinyl)-6-(trifluoromethyl)pyrimidine

HRID 2084256Notes

Reaction equation

HRID 2084256 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.[Cl:18][C:19]1[C:25]([CH3:26])=[CH:24][C:22]([NH2:23])=[C:21]([O:27][CH3:28])[CH:20]=1>>[Cl:18][C:19]1[C:25]([CH3:26])=[CH:24][C:22]([NH:23][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)=[C:21]([O:27][CH3:28])[CH:20]=1

Participants

3

Reactant 2

HCID 807824-Chloro-5-methyl-o-anisidineHCID 14859904-Chloro-2-(pyridin-3-yl)-6-(trifluoromethyl)pyrimidine

Product 1

HCID 227323834-(4-Chloro-2-methoxy-5-methylanilino)-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 4-chloro-2-methoxy-5-methylaniline (50 mg, 0.289 mmol) similar to Example 117 and isolated as a tan solid (26 mg, 34%). 1H NMR (CDCl3): 9.65-9.63 (m, 1H), 8.75-8.70 (m, 2H), 8.18 (s, 1H), 7.46-7.41 (m, 1H), 7.36 (s, 1H), 6.97 (s, 1H), 6.87 (s, 1H), 3.91 (s, 3H), 2.42 (s, 3H).

Sources & evidence

ORD record
ord-a3621243c1704f868d247de3760849ca
Source dataset
uspto-grants-2004_04
Patent number
US06716851B2

Reaction notes

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