5-Fluoro-o-toluidine → 4-(5-Fluoro-2-methylanilino)-2-(3-pyridinyl)-6-(trifluoromethyl)pyrimidine

HRID 1765191Notes

Reaction equation

HRID 1765191 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.[F:18][C:19]1[CH:20]=[CH:21][C:22]([CH3:26])=[C:23]([CH:25]=1)[NH2:24]>>[F:18][C:19]1[CH:20]=[CH:21][C:22]([CH3:26])=[C:23]([CH:25]=1)[NH:24][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 677745-Fluoro-o-toluidineHCID 14859904-Chloro-2-(pyridin-3-yl)-6-(trifluoromethyl)pyrimidine

Product 1

HCID 99462684-(5-Fluoro-2-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 5-fluoro-2-methylaniline (36 mg, 0.290 mmol) similar to Example 58 and isolated as a tan solid (4 mg, 6%). 1H NMR (CDCl3): 9.71 (dd, J=0.80, 2.3 Hz, 1H), 8.74–8.71 (m, 1H), 8.68 (dd, J=1.7, 5.0 Hz, 1H), 7.72 (s, 1H), 7.44–7.39 (m, 1H), 7.33–7.28 (m, 2H), 7.02–6.95 (m, 1H), 6.67 (s, 1H), 2.29 (s, 3H).

Sources & evidence

ORD record
ord-044746c8be854dc3a4c5f6f7179e6d72
Source dataset
uspto-grants-2007_06
Patent number
US07226927B2

Reaction notes

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