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

HRID 2084109Notes

Reaction equation

HRID 2084109 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.[CH3:18][O:19][C:20]1[CH:21]=[CH:22][C:23]([CH3:27])=[C:24]([CH:26]=1)[NH2:25]>>[CH3:18][O:19][C:20]1[CH:21]=[CH:22][C:23]([CH3:27])=[C:24]([CH:26]=1)[NH:25][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 995005-Methoxy-o-toluidineHCID 14859894-Chloro-2-(pyridin-4-yl)-6-(trifluoromethyl)pyrimidine

Product 1

HCID 101331274-(5-Methoxy-2-methylanilino)-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 5-methoxy-2-methylaniline (27 mg, 0.193 mmol) similar to Example 13 and isolated as a pink solid (23 mg, 33%). 1H NMR (CDCl3): 8.77 (d, J=5.7 Hz, 2H), 8.27 (d, J=5.7 Hz, 2H), 7.32 (s, 1H), 7.26 (d, J=9.0 Hz, 1H), 6.99 (s, 1H), 6.70 (s, 1H), 6.85 (dd, J=2.7, 8.4 Hz, 1H), 3.82 (s, 3H), 2.24 (s, 3H).

Sources & evidence

ORD record
ord-a9c68165ee4244c88b6c6984342f903c
Source dataset
uspto-grants-2004_04
Patent number
US06716851B2

Reaction notes

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